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West Chop Vacation Rentals Martha's Vineyard

West Chop Homes for in Rent Martha’s Vineyard | MV Seacoast

Master Bedroom

Bedroom 2

Part of an acre+ compound on the bluffs of Chappaquiddick this beach cottage offers a spectacular view of Edgartown's Lighthouse and outer harbor.  Privacy landscaping & private beach just down a stairway guarantee a peaceful vacation amid Chappy's gorgeous vistas. You can walk to the ferry dock in 5 minutes.
Chappaquiddick Rudder cottage furnished with cottage antiques. 
TENANT supplies sheets and towels.

4 Caleb Pond Lane - "Rudder"

Bedroom 3

Bedroom 4

Bedroom 5

Welcome to the gentle breezes of Ocean Pines in Katama.  This 2866 sq. ft. contemporary home and privately sited on 1 acre offers easy summer living near South Beach and a few minutes from the village of Edgartown.  There are two ensuite master bedrooms. The media room has a  plasma TV.  This room can double as a 5th bedroom with its daybed & trundle that can combine into a king size bed. The basement game room has ping pong table.  The private association tennis courts are nestled in the woods next door.  Smooth paved roads and safe bike paths provide easy access to South Beach and Edgartown Village. Multiple AC splits provide cool air throughout the house.

10 Old Dunham Corner Way

READY FOR 2025 BOOKINGS!
Beautifully crafted post & beam home nestled in a pastoral setting. To reach this three-bedroom air-conditioned oasis you drive past grazing Alpacas before turning right at the strawberry field. You enter thru the farmer's porch into an open floor plan. Three skylights in the family room provide natural sunlight. The dining area accommodates seating for eight. The kitchen includes all new appliances. The two bedrooms on the main floor each have large windows to take advantage of the island breezes and a set of French doors that lead to outdoor decks. The second-floor bedroom has an en-suite powder room and a private deck that provides a great spot for star gazing. Recent improvements to this charming house include a large screened porch off the great room, a completely remodeled master bathroom, updated to 3.5 bathrooms,  a new TV room and another primary bedroom en suite with a walk-in closet.

26 Bridle Path Road

Beautiful little 2 bedroom home in a quiet neighborhood.  It is brightly decorated and nicely furnished with an open living area porches & new appliances.  Impeccably maintained cottage used to be in the Campground before moving to the edge of East Chop.

12 Chickawaukee Street

Bedroom 6

READY FOR 2023 BOOKINGS! 
A Martha's Vineyard Landmark property on a small road in West Chop just a few houses up from the original Holmes Hole landing. There's a water view from the end of the driveway and the beach is a few steps away! This Historic Cape is minutes from downtown and the ferry yet nestled in a quiet residential neighborhood on an oversized lot for plenty of privacy and space for the family to spread out. A visit to the MV Museum and you will learn of Captain Eldridge and this home that was once home to his daughters. This is not a restored or renovated property but rather a well-cared-for home that is remarkably preserved as if frozen in time.  Decorated and adorned by a family that has called this place their home for many generations.  Open light airy high ceilings, spacious living room and a large dining room with a formal dining table that seats twelve.  Six bedrooms.  2 queen bedrooms, the Master being on the main floor with an ensuite Bath, sitting area that steps out to a brick patio for morning coffee or a little stargazing before bed. Another queen and a shared full bath on the main floor. 3 bedrooms upstairs. 2 of the twin bedrooms share a half bath with a full bedroom upstairs.  Sunny deck off kitchen for outdoor meals. Both a gas and charcoal grill.  Brick patio off the dining room for quiet reading or evening cocktails.  Back and side yard ideal for croquet bocce and more fun. There are bicycles and kayaks as well as an outdoor shower. Easy walk to the beach with views of East Chop main street and West Chop lighthouse views of the sunrise.  Relaxed Vineyard comfort that has been enjoyed since the 1900s for one or two families!  Linens are not included. Ferry tickets may be available at the tenant's expense.  MORE PHOTOS COMING!

22 Grove Avenue

READY FOR 2023 BOOKINGS! This darling 2-bedroom cottage is right in Edgartown Village. Meant for a small family or 2 couples the convenience of walking to town and Fuller Street Beach for a fair price is priceless! Enjoy the recently updated accommodations inside and out with comfortable furnishings, an outdoor shower and a front porch that is a great place to get some sun or have a cocktail after a day at the Beach. There is adequate parking for 2 vehicles. On-site washer and dryer. *Note Linens and Towels are not provided. Tenants may inquire on renting or bring their own.

5 Silva Lane

Ready for 2025 rentals!
WOW Is the only way to describe this Newly built Country Colonial in town Vineyard Haven.  Stainless kitchen has Granite counters 4 large bedrooms and 2.5 bathrooms. Enclosed outdoor shower. Green grass to run barefoot patio on lowest level back sun bathing deck off of the kitchen for easy snacking covered country porch for shade lovers and the landscaping is just beautiful.  This is a home you'll love to re-rent year after year!

206 Spring Hill Road

Bedroom 7

Enjoy the best of Oak Bluffs from the cornerstone of Ocean Park.   This elegant home overlooking Nantucket Sound is one of the premiere houses on Martha's Vineyard. A glass enclosed porch with antique wicker swings is the perfect spot to enjoy band concerts in the gazebo or view the annual August fireworks display. Wide porches envelop three sides of the house a five minute walk from Circuit Avenue the Flying Horses Carousel and the ferry terminal. 
----Six airy bedrooms and an open attic loft with picture windows and two skylights.  Large den spacious living room with a jukebox and game table and fully equipped antique pool room. Newly renovated eat-in kitchen. Hardwood floors and high ceilings throughout. Enclosed yards are large enough for several tents. Ideal for vacationing weddings reunions retreats and corporate events

101 Ocean Ave

Situated with two other houses on a magnificent 88 acre ocean-front property this secluded barn house has a 2 story living room with oak beams fieldstone fireplace and sliding  glass  doors overlooking the deck a long sweeping meadow and private beach.  Loft has queen bed 2nd bedroom has pull out couch (Single). Master Bedroom with Queen. Large estate offers nature walks and trails two tennis courts and a basketball backboard.  Kitchen is modern neat and cheerful. Evokes the flavor of an artist's studio in Cornwall England.

14 Quammox Rd

Tranquility on Chappaquiddick.  Charming restored antique farmhouse on 80 acre estate. Eat-in country kitchen large sunporch fabulous views of South Beach and Katama Bay private beach.   The 2nd floor was renovated in 2010 with new sheetrock & insulation and redone floors.  At that time the screened porch was turned into a year round sunporch.  As of 2013 there is a large TV with Blu-Ray player and Hulu.  and The compound has 2 tennis courts and a basketball backboard.  May moor small boat good warm water swimming no traffic and lots of room to roam.  Prohibited - spike heel shoes pets open fires and off road driving.

8 Quammox Rd

Ready for 2025 bookings

Part of an acre+ compound on Chappaquiddick this cottage offers some of the best views on the Vineyard--the spectacular Edgartown Lighthouse and Outer Harbor.  With some tackle & a good book you'll be all set for a peaceful stay amid Chappy's gorgeous vistas. You can walk to the ferry dock in 5 minutes.  New owners in 2015 have improved the views raised the foundation redone the kitchen and deck and installed WiFi.

6B Caleb Pond Lane-Mizzen

READY FOR 2023 BOOKINGS! This breathtaking West Chop waterfront property boasts a prime location with stunning views of sailboats entering the Harbor. The property features a private dock that is shared with a neighbor, providing direct access to the water. The beautifully landscaped yard enhances the natural beauty of the area, and a set of stairs leads down to the water, allowing for easy access to the private dock. The location of this property is highly desirable, as it offers the convenience of being within walking distance of the town. In addition, the backyard provides the perfect spot to swim and enjoy the water. This exceptional property offers the perfect blend of luxury, convenience, and natural beauty, making it a truly remarkable find.
This listing is for the Main House Only. ----If you need additional accommodations ask about adding the in-law apartment over the garage for an additional fee. It offers a King bed bathroom w/shower kitchenette and a Living area w/TV.

55 Harborview Lane

Ready to book in 2025!

Beautiful modern colonial - style house on 2 acres of private landscaped property within walking distance of downtown Edgartown and Fuller Street Beach.  The house has sweeping views of Nantucket Sound and is accessed by a long private driveway.  The house itself abuts ten acres of ocean front conservation land that adds to the property's feeling of privacy and space.  All bedrooms have views of the water and the great room (living room and dining room combined) has a two-story living room with views of the water and a twenty-six foot wall of windows.  There is parking for approximately four cars on the gravel driveway.

7 Angevin Lane

Reverse contemporary designed with pleasing architectural angles to catch an ocean glimpse or open fields of conservation land. Cathedral living room open kitchen/dining plan with sliders to the large wrap-around deck. Perfect vacation home just a five minute walk to beautiful South Beach!  For 2019 many improvements - new kitchen counters cabinets & sink new 2nd floor shower and LR couch.

7-A Katama Farm South

READY FOR 2024 BOOKINGS! 
Mill Pond House is a completely restored 1840s farmhouse adjacent to the famous Mill Pond in historic West Tisbury. Remodeled by the present owner, it is beautifully appointed with antiques charming accessories and comfortable furnishings. An old pine floor and columns add to the ambience of the interior. A new heating and cooling system throughout! The first floor has been converted to an open space plan with a cozy living room a smart TV, fireplace(no burning), a fully equipped kitchen and a charming dining area seating eight. Adjoining is a double bedroom with half-bath as well as a screened porch with a dining table TV seating area and beautiful view of the spacious deck container plantings and yard rolling down toward to the Mill Pond. The main house is 2700sf. Upstairs there is a king, queen and twin bedrooms; two with a beautiful pond view. Laundry conveniently located in one of the two full bathrooms. THE SUMMER HOUSE An adjacent old barn converted to a studio with living space a half-bath bar sink and WiFi serves as a wonderful private space for work or play. Children will delight in a full size playhouse toys and games. A fence around the front of the property secures small children. The back yard and vista provide a lovely pastoral setting often enhanced by brilliant sunsets. Linens need to be supplied by tenant/rented. BRAND NEW MINI SPLITS A/C!

709 Old County Road

READY FOR 2024 BOOKINGS! 
3 bedroom Cape just a 15-20 min walk to downtown OB and beach.  Open floor plan has large living/dining/kitchen area on first floor along with 2 bedrooms and both full bathrooms.   Upstairs is one huge room with 2 twins at one end and a family room w/kids' TV at the other end.  House is comfortably furnished and has Hi-Speed internet & cable TV on main floor.  Large landscaped yard. Close to everything but out of the traffic - Bike to Inkwell in under 5 minutes! *Linens not provided by owner

73 Wing Road

Enjoy the best of both worlds in this delightful Village property.  The original wing of the house is very quaint with a wood-paneled dining room & brick fireplace updated kitchen and two cozy bedrooms.  The recent addition has central AC a large family room with wet bar on the first floor and a beautiful Master Suite upstairs with views of Nantucket Sound.  All just a few blocks from Main Street and the beach.   The bedrooms in the original section of the house have wall-unit AC and newer window treatments.  Also a bigger outdoor shower and new grill. Studio with A/C and full bath available for July and August rentals.  Property overlooks Sheriff's Meadow Sanctuary with water view from upstairs master bedroom.  Key to private Black Point Beach is provided. Sleeps 9 in season with studio /7 off season without studio.

23 Pierce Lane

You will have amazing views from this well-maintained beach house on Upper Chilmark Pond. Boat across the pond to gorgeous Lucy Vincent Beach or relax on the spacious deck overlooking the pond the dunes and ocean. This home has an open floor plan perfect for a relaxed vacation. The master bedroom and great room (living room/dining room/kitchen) open onto an expansive deck through sliding glass doors. With lots of glass this home is light and airy. A convenient location (an easy drive to Chilmark Community Center the Chilmark Store Alley's etc.) and a truly spectacular setting. Enjoy magnificent sunrises on the beach!

22 Tilton Cove Way

READY FOR 2025 BOOKINGS.

Beautiful new contemporary in Dodgers Hole.  Open living-dining-kitchen Great Room with vaulted ceilings and beach stone fireplace.  Gourmet kitchen granite counter tops. 2 flat screen TV's.  Two master bedroom suites on the 2nd floor. A large deck and landscaped yard are perfect for outdoor entertaining or relaxing after a sunny day at the beach.
Property offers central AC

7 Sparrow Lane

This charming & unique house has graced Ocean Park for more than 100 years.  New kitchen and bathrooms with granite counters central AC Wi-Fi and more.  You can walk to everything. The child friendly beach is just across the road where you can make sandcastles in the sand or stroll along the boardwalk above the beach and rest on a bench facing the water. Or stay at home sit on the porch and gaze over Ocean Park with its iconic gazebo. Have your own private front seat to the concerts and fireworks in Ocean Park during the summer.

37 Ocean Park

This is a large single house with 2 levels 4 bedrooms on 2nd level master bedroom with separate full bath  front porch with lounging chairs full deck with table chairs and gas grill off dining room through sliding doors.  Good-size yard and walk-to-town make for a terrific family accommodation.  The finished basement has high ceilings and a media space perfect for the kids to hang out! The basement has a full bath with a shower and washer/dryer. The studio suite above the attached garage is very convenient for in-laws and guests.  It contains a Queen bed TV kitchenette full bath with shower private deck & grill.  Doors between the units can be locked for privacy.  There is an outdoor shower for use to remove sand.

80 Midland Avenue

READY FOR 2025 RENTAL SEASON!!!
Lovely well-appointed Condominium in Tashmoo Woods with association swimming pool tennis courts and beach. Open Floor Plan with Cathedral Ceilings. Very light. Windows all along the back side of the unit. Door to back deck and wooded/garden area.  Living Room with Fireplace. Spacious Kitchen and separate Dining Room. First floor Den. Lovely open rung wood railed stairway to 2nd Floor leads to Two Bedrooms each with a private bath.  The finished basement has a rec room with large flat screen TV sofa bed and full bathroom.
Property accepts two weeks minimum rentals.
The owner accepts pets under consideration.

256 Sandpiper Lane

Enjoy luxury on the Vineyard. Beautiful 3 bedroom home with beach stone fireplace. Gorgeous "Costa Esmeralda" granite counter tops with solid cherry cabinets French doors to patio 3.5 marble bathrooms with Calcutta gold marble master bath has rain shower with cast iron herring bone tub. Master has walk in closet. All new designer furniture. Custom stairways with entertainment center in basement with 52 inch plasma screen. Enjoy high speed internet with two additional plasma TV's. Close to bike path for easy ride into town. Short walk to beach. Backyard cobblestone patio and outdoor shower complete this wonderful luxurious getaway.
*Linens and towels are not provided. Tenants may use a linen rental service or bring their own.

36 Winne

Ready for 2025 bookings.

Historic Cape reverse set up, with living area, kitchen and powder room on the upper level with spectacular ocean views and the remaining living space on the lower level, consisting of an additional family room with a fireplace and double sofa bed, four bedrooms and two bathrooms. Upstairs the kitchen is fully equipped to create any meal. The living areas include dining as well as a tv and of course the panoramic ocean view. This private beachfront home is set back on one acre of lush lawn and landscaping. Be sure to meander to the beach which overlooks the sound depicting a clear view of the steamship authority ferry and various fishermen. You are minutes from the village of Oak Bluffs and an East Chop stroll.

BR1 King en suite with shower stall, 1st floor
BR2 Queen, 1st floor
BR3 Double, 1st floor
BR4 (2)Twin beds, 1st floor
Hall bath with tub/shower, 1st floor
Double sofa bed, 1st floor sitting room
Half bath, 2nd floor

10 Temahigan Ave

READY FOR 2023 BOOKINGS! Located in the heart of Oak Bluffs this spacious Campground cottage offers a very convenient location.  Minutes away from all the town shops local beaches beautiful Ocean Park and the Oak Bluffs ferry terminal.  Sleeps up to 8 people, has a fenced-in yard and onsite parking and a great covered porch for relaxing on those lazy days.  A great place for your summer vacation!*Linens and Towels not provided by owner

5 Rock Ave

READY TO BOOK FOR 2025 SEASON!!
 Simple Elegance in Chilmark! Only a mile away from Lucy Vincent Beach this refined beach house is wheelchair accessible has 4 bedrooms and floor to ceiling windows in the Kitchen & Dining Room allowing for superb natural light. Centrally located between Middle & South Road in Chilmark this home is perfectly situated to afford you privacy and proximity to Chilmark town center. Hollywood in Flip Flops is the best way to describe this rare gem of a home. It even has an exercise pool.

6 Trails End

READY FOR 2025 BOOKINGS! 

Lovely 4-bedroom, 2bath Colonial Saltbox in Katama.  Located on a quiet road off Herring Creek exactly mid-way between South Beach and Edgartown Village. This natural light-filled home has a modern kitchen, an open floor plan and glowing hardwood floors beneath your feet. Warm, spacious and inviting whether you are inside or outside. Enjoy a refreshing outdoor shower after a day at South Beach. Relax inside with A/C provided in all areas. There is a full laundry on the premises and everything you could need to feel at home at your MV retreat! A very reasonably priced home in a very great location! This home does not provide linens or towels (tenant may bring their own or rent).

20 Prada's Way

Part of a large private waterfront estate. This 2 bedroom 2 bathroom "guest house" feels more like a regular home.  All light oak floors throughout. The kitchen has new appliances and is very expansive. The living room is also large enough for family to gather. Both bathrooms come fully equipped and are also very spacious.  On the grounds of this estate, there are two tennis courts, a basketball backboard, hiking trails, play-set & fixings for badminton, softball and croquet.Sure to be a memorable vacation for your family and guests at this exclusive compound. On this 80 acre compound there is a 6 bedroom Farmhouse 2 bdrm Retreat and 2 bdrm Barn/house that may be rented separately. Ask your Rental Agent for details.

12A Chasin Road

Come and enjoy this light-filled, beautifully maintained three-level contemporary home complete with gardens, a landscaped yard, and a children's backyard playground.
The main level features an open kitchen, dining, and TV/living room area, all leading to an expansive deck perfect for large outdoor dining and seating areas. Designed for easy vacation meals, entertainment, and relaxation, this home also includes a separate living room with a fireplace and an en-suite master bedroom with a queen size bed. On the second level, you'll find two additional queen en-suite bedrooms. The lower level of the house offers a well-equipped children's playroom, an adult workout area with a treadmill and stationary exercise bike, a TV room, an office nook, and a full bathroom. Additionally, the lower level features a den with a queen sleep sofa, accommodating extra guests comfortably. Meadow View Farms is conveniently located near town beaches, Farm Neck Golf Club, and more, sitting on one acre of beautifully landscaped property. Enjoy summer days on the magnificent back porch overlooking an additional patio and a swing set.
The home includes association tennis courts, an outdoor shower, central AC, and all the amenities you need for your Vineyard vacation. A porta-crib is also available upon request.

17 High Meadow Lane

READY FOR 2023 BOOKINGS! Great central location! Close to the Lagoon bike path and town. Three bedrooms two baths with additional space in the second floor loft. Home features an open living kitchen and dining area as well as a full bath and queen bedroom (with privacy curtain) on the first floor. The second floor consists to 2 bedrooms (1 queen 1 twin) full bath and loft area. There is a covered front porch a side screened in porch and an enclosed outdoor shower. Home is fully equipped with all the modern conveniences.

23 Beacon Ave

READY TO BOOK FOR 2025 SEASON!!
This very comfortable property will be one the family or friends want to return to year after year.  A clean well kept rental with two outdoor showers and a large deck on the front taking in plenty of sun! 4 Bedrooms with one being a large room on the 2nd floor that has King at one end,  4 twins at other end and Queen sleeper in the middle.  On the first floor  1 queen size bedroom. Primary ensuite bedroom with king size bad.  Living room  open to the Kitchen with an island and dining area make this a great social house for get togethers and barbecues !
Studio above garage - queen size bed plus a futon.
Property is located in the very popular area of Windsor Drive.  Close to the bike path. Across VH/Edg Rd is Felix Neck Sanctuary,  lovely walking neighborhoods of Majors and Hidden Coves connecting to Sengy Pond looking out to State Beach. Well worth the price!

1 Essex Court EDG

READY FOR 2024 BOOKING! This very well maintained 4 bedroom, 3 bath home recently updated with new wood flooring, appliances, A/C and more.  Tucked into Hidden Cove, an established quiet neighborhood in Oak Bluffs - central to all down Island towns. 
You are less than a 10 minute drive to the beach. There are association tennis courts to enjoy and you are located just off a main bike path that can bring you to any town. Easy access to Sengekontacket Pond. This 3 level home has a Queen bedroom as well as a 2 twin bedroom on the lower level. On the second level is a Queen bedroom and a Master Queen ensuite with its own access to the deck. All Linens, with the exception of towels, are included for your stay.

19 Hidden Cove Rd.

READY FOR 2023 BOOKINGS!

With endless water views, remodeled, fully updated, and steps from a sandy beach excellent for swimming, our walk-to-town home has been gorgeously redone and designed with a simple yet sophisticated Martha's Vineyard-meets-California feel. 
Airy and uncluttered, with central air conditioning, and wide open ocean views, the home has 4 bedrooms and sleeps 9. We have the rare (in Oak Bluffs) benefit of being buffered by a generous lawn; so you can enjoy all the beach-going and socializing of Inkwell Beach and the Ocean Park area, but we are set back a little, with more breathing room. 
Inside you'll find wide-plank pine floors, a kitchen with a cook's view to the sea, and pro-style appliances including: dishwasher, gas range, French door refrigerator with ice maker & filtered water, and a full-sized washer/dryer set apart in its own laundry room. There's a back entrance here, off the wraparound porch, for easy access to, and from, the enclosed outdoor shower (outdoor shower is in addition to subway tile/glass door indoor shower). There is a king-size bed in a larger than usual (for OB) master BR. Plentiful seating inside at a large table as well as at bar stools at the butcher-block topped island/bar area, as well as the spacious, level, wraparound porch (3-sided). You're perfectly situated for the annual fireworks, dining/coffee/cocktails outside or just watching the world go by.*Linens not provided by owner

4 Canonicus Ave

UPDATED FOR 2023 BOOKING! Spectacular 18th century waterfront home overlooking the heart of VH harbor with  private sandy beach.  Watch the sunny activity in the harbor from the deck/porch or take a stroll into town. Comfortably furnished with antiques that will make you feel like you have gone back in time;  original Currier & Ives posters & chifforobes abound.  With newer wood floors downstairs and original wide pines up the main floor has living room with Steinway piano & marvelous views dining room fully equipped kitchen and glassed-in porch.  The 1st floor Master Suite has a Queen bed and a Full bed in the study/sitting room. 2nd floor has 4 bedrooms and 2 baths. All beds have newer mattresses. A great setting with landscaped lawn all around; the wraparound deck has wisteria vines climbing up & over and gorgeous iris beds below.
The property has Smart TV.

39 Crocker Avenue

UPDATED FOR 2023 BOOKING! Lovely contemporary cape in East Chop with 4 bedrooms a loft and 2 full baths. Cathedral ceilings and skylights fill the house with light. Walk to town, beaches, shopping, and ferry.  Cable TV service includes DVR.  A very quiet location just 1/2 mile to the beach and to Circuit Ave. This is vacation central.

2 Monahegan Ave.

READY FOR 2024 BOOKINGS! Country living at the Sea Side!  Beautiful reverse contemporary with a bright open floor plan. In Katama this is just a short walk to South Beach. Large open lot for kids and outdoor play.  This 3 bedroom 2.5 bath home is filled with natural light and open and airy. There is also an outdoor shower. Beautiful Henry Link wicker furniture all newly covered. Spacious deck to enjoy evening dinners or to lounge after a day at the beach.

11 Katama Farm South

READY FOR 2023 BOOKINGS! Adorable contemporary cape with cathedral ceilings. This is a very comfortable 3 Bedroom 2 Bath house with A/C in a great neighborhood that's safe for children and pets (with owners prior approval). First floor has open kitchen , dining and living room. Sliding doors to a spacious new deck and outdoor shower. A full bathroom with a washer & dryer are connected to the master bedroom. Upstairs there are two more bedrooms with a shared full bath in the hallway.  Close to the Oak Bluffs town line, Felix Neck Wildlife Sanctuary  and  just 2-3 miles to town and beach. Short paved quiet dead end street with no traffic. Great for bike riding skate boarding roller skating etc. Central to all down Island towns that are each only 5 minutes away by car. Jump on the bike path that also leads to the town of your choice. Monthly and off season rates available-inquire with rental department.

4 Essex Court

FERRY TICKETS PROVIDED!
Modified 4-bedroom cape across from Felix Neck Bird Sanctuary - quietly tucked away on a private wooded lot. Fully appointed kitchen with dining area leads out to deck complete with outdoor furniture. Large brick fireplace in the living room. On the main floor there are two bedrooms one with an antique queen sleigh bed and the other with 2 double beds.  The upstairs opens to a loft casually appointed as an extra family room.  The second floor also has two bedrooms one with a king bed and the other with a queen & single bed. Located in a quiet private development complete with grassy common land across the road for outdoor fun. Great central location - just a 5-minute drive to all three down Island towns and beaches!

3 Laura's Way

READY FOR 2024 BOOKINGS! Sparkling contemporary in a wonderful family vacation neighborhood close to townBeach and public access to Edgartown Great Pond.  Large front deck.  The main floor has a spacious living room with cathedral ceiling open kitchen-dining area and slider to a screened porch. The master bedroom suite is on the main floor.  Three more bedrooms and a full bath are located upstairs.  You can bike in minutes to South Beach or the picturesque village of Edgartown.

175 Meetinghouse Way

Large Victorian beautifully furnished in wicker with stone fireplace in the Living Room large stained-glass window in the Dining Room wraparound porch and large fenced yard.  This magnificent home is bright and airy with lovely wood flooring and fresh paint on many walls.  There are five bedrooms and two bathrooms upstairs.  Fantastic location surrounded by Oak Bluffs' picturesque Victorians and an easy stroll to town or beach.  Recent improvements include new bathrooms, updated kitchen appliances and furnishings.

28 Pequot Ave.

READY FOR 2023 BOOKINGS!
One half acre wooded lot - very private with a small courtyard in back. Eat-in kitchen dining room living room open area with cathedral ceiling.  First-floor bedroom has one queen bed.  There are two upstairs bedrooms one with a Double Bed and the other with 2 Queens. Nice wrap-around deck and outdoor shower.  Recent improvements include new sectional couch light fixtures 46" flatscreen TV and hardwood flooring in Living Room. Updated bathrooms and kitchen with granite counter top. NEW PHOTOS COMING!

2 Schoolhouse Rd

READY FOR 2024 BOOKINGS! A modest 3 bedroom ranch is tucked into a fabulous location! Just a short distance from the boat landing on Katama Bay and one half-mile from South Beach. In the recent renovation brings new paint updated kitchen, bathrooms and flooring. This property has a great back yard and an outdoor deck to BBQ and an outdoor shower. This is a wonderful location to walk or jog in the morning/evening. Pack a picnic rent Kayaks and launch at the landing and paddle to the South Shore for the day! And on your way back you can go clamming for your dinner! (Town of Edgartown sells the clamming license). Close to South Beach and close to the bike path and VTA bus to ride into Edgartown.  Also close to The Dunes South Beach Restaurant. A great location for a wonderful vacation!

11 Town Lot Road

A classic Vineyard waterfront home that looks across a beautiful lawn to Katama Bay, Chappaquiddick and distant Edgartown harbor.  There is a sand & pebble beach a small bath house and a long private dock with 6ft draft at high tide 2ft. at low.  The house is attractively furnished light and airy and tastefully decorated in summer colors. A new French front door will enhance already spectacular waterviews. The house has three separate living areas; living dining room and sun room with entertainment center.  A terrace on the west side of the home is a wonderful place to relax.  The sitting room upstairs has a 2nd flat screen TV. Store your bicycles in the garage for use on the nearby bike path along Katama Road.  Enjoy the outdoor shower after a day at your own private beach!

17 Edgartown Bay Road

If you're looking for a nice house for 6 in a quiet neighborhood but located between South Beach and Edgartown Main Street then you will like this property. The furnishings are very comfortable and the wrap-around deck is a joy to sit on when the sun gets too hot for the beach and it's time for a BBQ and cocktails. With an outdoor shower to make your vacation easier and Gas grill to help you feel at home you can't go wrong.

16 Zoll Rd.

READY FOR 2025 BOOKINGS! A myriad of beautiful lush hydrangeas welcome you to this tucked away property just a short stroll to Downtown Edgartown Village, you will find this pristine 4 bedroom 3 bathroom one level home with generous landscaped backyard. Upscale well equipped kitchen with adjacent dining area. Double sliders open to outdoor furnished deck with gas grill and outdoor shower.

6 Mariner Circle, Edgartown

Delightful colonial style guest house on the 7 Angevin Lane property. Beautifully detailed 2 Bedroom 2 Bath Guest House with fireplace bay windows and glass doors look out to a water view.  Can be rented with the main house #90576 as a family compound or separately.

5 Angevin Lane

54 Kennebac Ave

Bedroom 8

Bedroom 9

Bedroom 10

Part of a large private waterfront estate the Main House has expansive views tennis court and private beach. Open floor plan great for large groups entertaining and corporations. Two tennis courts a basketball backboard hiking trails playset & fixings for badminton softball and croquet.  All light oak floors throughout. Two nicely furnished fully equipped kitchens one in front and one in rear with large roasting pit. There are three refrigerators a water cooler and an indoor water pump. The main house includes the use of the Beach Cabana with deck close to the Bay and the Studio for reading meditation & exercise. 2021 improvements include bathroom remodels and a new projection screen TV with AV system in the living room.   Sure to be a memorable vacation for your family and guests at this exclusive compound. On this 80 acre compound there is a 6 bedroom Farmhouse 2 bdrm Retreat and 2 bdrm Barn/house that may be rented separately. Ask your Rental Agent for details.

12 Chasin Rd

READY FOR 2023 BOOKINGS!
Located in a secluded neighborhood yet a short ten minute ride to town, this privately custom-built house is perfect to host your family during its Vineyard vacation. Set on over half an acre, the home has been meticulously maintained and upgraded. This 3 bedroom, 2.5 bath has everything: gourmet kitchen with all necessities; a/c splits; mesh wi-fi throughout house; perfect work-from-home office space; screened-in porch with bar; outside deck with hot tub; incredible landscaping; smart TV's.

64 Saddle Club Road

This luxury enclave, complete with 4 bedrooms and 3.5 bathrooms, is located in a private community that is centrally located and comprised of upscale properties. The simply elegant home is a brand new construction that is nestled in a woodland setting with quaint views of a golden meadow and a beautiful pond. The stunning property connects to miles of walking/hiking trails and a bike path to Farm Neck Golf Club, in addition to 3 down island towns and beaches. With carefully crafted architecture, this house is full of character and integrity. The contemporary design offers upstairs and downstairs master bedroom suites as well as a first and second floor family-style living rooms complete with plasma screen TVs. At the top of the winding staircase is the hallway that wraps around to observe the open entry hall below. Two additional bedrooms are located upstairs with a bath and the kitchen has gorgeous cabinetry with high end appliances. There is wide oak flooring throughout and gleaming marble tile detail in the bathrooms. Other highlights include french doors that open to a large deck off of the living and dining room, complete with a table that sits 8 people, a lounge couch, and chairs. Additionally, there is a stone patio off of the first floor master bedroom, a stone fireplace anchors the living room, and a large and spacious backyard borders the back of the home.

24 Paddock Lane

READY FOR 2024 BOOKINGS! This unique 3-level Vineyard style cottage perched on a 25' bluff offers you a panoramic view of the Lagoon's shimmering waters, picturesque sunsets, and Nantucket Sound. From across the bay, you can see and faintly hear the Vineyard Haven Ferry departing. Simply follow the wooded path leading to over 110 feet of your own private sandy beach with clean, calm waters which allows for safe kayaking and canoeing yet has the perfect breezes for windsurfing and sailing from your own mooring. 
This light-filled home has an open floor plan on the first floor with reclaimed chestnut floors and a tiled kitchen, large windows and spectacular water views. The lower level has a private bedroom with direct access to the rear deck and a large outdoor shower. The second floor features a master bedroom, with a full shared bath. There is also an additional bedroom (that doubles as an office) on this level along with a lounge area with sky and waterviews for miles. The home has central air conditioning, 4 televisions, and adjustable beds for your sleeping comfort. Outdoors, there is a flagstone patio, a deck for al fresco dining, and an additional patio area. The outdoor patio area and deck have breathtaking waterviews.

13 Hubbard Lane

Centrally located between the Edgartown and Katama sections of the island, 27 Schoolhouse is situated less than 10 minutes from Downtown Edgartown, South Beach, Morning Glory Farm, Edgartown Golf Club and Martha's Vineyard Airport.  It also provides convenient access to various underutilized roads that get you to all parts of the island.

This handsome home comfortably accommodates six to eight guests between three bedrooms and a loft space and has two bathrooms, onsite washer / dryer and is wifi enabled with flat screen TVs throughout.  While the natural breezes are plentiful in this area, mini-split units are located throughout the house to cool it on warmer days.   27 Schoolhouse is a tranquil retreat from the summer crowds where one can sit outside on the wrap-around decks to enjoy a morning coffee or an evening of grilling while gathering with loved ones.

27 Schoolhouse Rd

READY FOR 2025 BOOKINGS!
Custom Built 3+ bedroom home with beautiful waterviews of Lagoon Pond and just a walk down hill from the backyard to the beach.  Enjoy this uniquely private setting surrounded by 15acres of conservation land just minutes to downtown Vineyard Haven. 
A full kitchen and bar area leading out to the oversized garden patio. Sit with a book or enjoy an evening entertaining at home with family and friends. Take a refreshing outdoor shower after hiking the many nearby trails or a day at the beach. Relax with a soak in the spacious hot tub for eight.
The  Master Suite is on the 1st floor with a full tub and separate shower. The office with an additional trundle bed, a half bath, the outdoor shower and full laundry are also on the main level. The upper level has a two bedrooms  with a gorgeous view that share a full bath with a double sink and shower. 
The living room, dining room and kitchen share a bright open floor plan with high ceilings and large windows looking out to the pond.  Bike, kayak or just relax at this private retreat that is just around the corner from the ferry, shopping and a hop over the bridge to OakBluffs or turn left head to Edgartown.
This is truly a hidden gem to create many Vineyard  vacation memories!
MORE PHOTOS COMING!
*Monthly and off season rates available - inquire with rental dept.

80 Bellevue Ave VH

7 Katama South Farm

Beautiful Scandinavian Style brand new sophisticated Main House welcomes to the House On The Plains compound. Complete with pool, beautiful decking, screened porch and landscaping.
Main House can be rented together with a Guest House (see separate listing - 9 Katama Farm South - Guest House) or separately. Ask the agent about pricing.

Bedroom One: Second floor, 1 king bed, private outdoor space, indoor, outdoor heated shower, double sink, ensuite
Bedroom Two: Ground Floor; 1 king bed, private outdoor space.
Bedroom Three Lower Level: Twin Over Queen Bunk Bed, Private Bath, Shared Outdoor Patio
Bedroom Four Lower Level: (2) Extra Large Twin Beds Or (1) King Bed, Private Bath, Shared Outdoor Patio

Guest House:
Bedroom Five Guest House: Second Level: King Bed, Private Bath
Bedroom Six Guest House: First Level: Additional Sleeping Space With (2) Extra Large Twin Beds

9 Katama Farm South - Main House+Guest House

Brand New!!!

This sophisticated Guest House welcomes you to The House On The Plains compound close to South Beach. 
Complete with inground pool, deck and lawn area. 
Natural light and open concept living room, kitchen, dining area with vaulted celling and windows all around. Beautiful hardwood floors, gas fireplace, light wood beams above. Stylish Contemporary furnishings. Front loft area offers extra sleeping area..
Bright natural wood stairway in rear of house up to Primary Bedroom with a balcony and ensuite bathroom. 
One bedroom on the first floor with two XL twin beds. 
Lower level family room with its own exterior entrance.

9 Katama Farm South - Guest House

This stunning modern contemporary home boasts a unique reverse floor plan, offering a fresh and innovative approach to living. Upon entering the home, you'll be greeted by the spacious bedrooms on the lower level, each thoughtfully designed to offer ultimate comfort and privacy. On this level, you'll also find one full bathroom, beautifully appointed, adding a touch of luxury to your living experience.

As you make your way upstairs, you'll discover the living spaces, including an open floor plan that seamlessly integrates the living room, dining area, and kitchen. The kitchen is fully equipped with an ice maker, juicer, blender, and a variety of dining spices, providing everything you need to cook delicious meals at home. Open the three sliding glass doors to step out onto the large back deck, providing an ideal space for friendly get-togethers or simply enjoying some solitude.

For those who love the outdoors, this home offers the added luxury of an outdoor gas fireplace, furnished patio, propane grill, and grill tools, perfect for relaxing and taking in the beautiful surroundings. The third-floor primary bedroom is a true oasis, complete with its own private veranda overlooking the beautiful fields of Farm Institute, providing a tranquil escape.

Overall, this home offers the perfect combination of comfort, style, and convenience, making it an ideal choice for anyone looking to enjoy a truly luxurious living experience.

9 Mattakesett Way

Contemporary with a mid-century modern decor results in a truly unique beach house vibe. The details, many of which are tailor-made include custom headboards, a 12 x 4 foot Mahogany dining table, enhance the innate tranquility of the property, while the gourmet kitchen with dual ovens, downdraft Zline stove and wine cooler reiterate the glamour of the experience. There are two ensuite bedrooms on the main floor, one with a king size bed and access to the back deck, the other, queen bed. Two additional bedrooms on the second floor, as well as a finished lower level with a stunning Brunswick pool table, there is a full bathroom on this level as well. There is a 86-inch flat screen television in the living room and a 75-inch flat screen on the second floor landing, which opens to a private balcony. Enjoy the 22X40 heated POOL, surrounded by a striking blue stone patio that gorgeously contrasts the 1+ acres of lush green landscape. No outdoor shower, but an expansive deck with fabulous outdoor grill/kitchen and patio space for entertaining. Take in the stunning vistas of the Vineyard Golf Club and bask in the peace and quiet...

BR1 King Bedroom 5 piece en-suite, opens up onto back deck, Main floor, BR2 Queen Bedroom en-suite, Shower only, ceiling fan, Main Floor, BR3 Three Double Beds, Second Floor, BR4 Queen Bedroom, ceiling fan, Deck, Second Floor. Shared Bathroom Second Floor. Half Bath off Kitchen on Main Floor

61 Edgartown Meadows Rd

Recently Renovated. A few blocks from Lagoon Pond. 1.5 miles from VH center. VH West Lagoon. A/C. Wifi. Laundry on site. Deck with Grill.
Additional Amenities: High Chair. Pack -n- Play.

36 Park Ave

READY FOR 2025 BOOKINGS!!

This 3 bedroom 2.5 bathroom property is nestled in a quiet neighborhood midway between Oak Bluffs and Vineyard Haven. Only a stones throw away from the Sailing Camp on Barnes Rd. this house is a 10 minute car drive and 15-20 minute bike ride away from both Oak Bluffs town center and Vineyard Haven town center. Provided with bicycles, beach chairs and beach blankets so you can enjoy the quintessential vineyard experience. With a deck that spans the back of the house that not only holds a propane grill but is also attached to a screened in porch to make entertaining a dream. Just off this same deck is an enclosed OUTDOOR SHOWER making rinsing off from the beach and heading right inside seamless. This property also has a library nook with games for family entertaining. Central A/C, WiFi, Washer/dryer, Fire pit. You will love this property!

50 Pondview Dr

Enjoy the luxury, spaciousness, and privacy of a 5,850 square foot retreat nestled amidst nature and surrounded by an Egyptian Lotus Pond and pasture with alpaca, sheep, goats & mini donkeys. Three floors of living space provide ample opportunities for family gatherings and peaceful "me" time. This spectacular Sanctuary can sleep up to 22 and boasts a library, multiple decks, a bar & billiard room, and optimal spaces for entertaining, relaxing, and enjoying the surroundings- indoors and out. Enjoy the proximity to Lambert's Cove Beach or explore the many beaches and ponds on Island. After a leisurely day in the sun, cool off in the outdoor shower and enjoy a cocktail while listening to your favorite tunes with Sonos speakers throughout the house. With 4.6 acres, there's plenty of backyard space for lawn games and family fun. And indoors, there are 5 TVs, including an 81-inch screen to view a movie or catch up on your favorite TV show. There are books to read, board games to play, and memories to be made. This is a one-of-a-kind setting for your one-of-a-kind vacation.

67 Hidden Village Rd

READY FOR 2025 BOOKINGS!!!

Waterfront with Mooring (5ft)!!! This beautiful property is located very close to downtown Edgartown yet still has the privacy of being out of sight and right on the water. With two spacious bedrooms and two full bathrooms, this house is a perfect getaway spot for a small group. If you love the ocean you will love this house!
Beautifully located on Sengekontacket Pond.
Sengie, as it is familiarly called, is one of the most visible coastal ponds on the Vineyard, separated from Nantucket Sound by the scenic Beach Road which runs along the shore from Edgartown to Oak Bluffs. On the Edgartown side it is called Anthier’s Pond, while Sengekontacket lies on the Oak Bluffs end. A popular public bike path runs along the pond side. Rich with bay scallops and quahaugs, the pond is a haven for shellfishermen. Shorebirds forage for food in the salt marshes and nest at Sarson’s island in the center of the pond. Rounding out the colorful scene are kayakers and windsurfers in the summer months, flyfishermen in the fall.
Two tidal inlets running under bridges connect the pond with Nantucket Sound.

189 Boulevard

Right Next To The Beach! Right In Town!
This 1 bedroom 1 bathroom apartment is located in downtown Oak Bluffs. The property is located on ocean ave which circles Ocean Park. Don't have a ferry reservation? Don't worry! The proximity to the Oak Bluffs ferry terminal can hardly be beaten. Everything inside is set up simply for a seamless vacation. New Floors! The location will have you in the center of all the action in Oak Bluffs. Book Now!

101 Ocean View Ave A

This lovely, recently built home is set right outside the center of Oak Bluffs. This is a house you will want to rent year after year. This spacious 2 bedroom 2 bathroom house has many great features that make it a wonderful stay like a large outdoor shower for washing off after the beach and a large screened in porch set up for indoor/outdoor dinning. Not to mention the open kitchen with butcher block countertops, recessed lighting and new appliances which will allow you to cook like a top chef without missing out on spending time with your company. The convenience of this property can hardly be beat. All of the action on Circuit Ave in Downtown Oak Bluffs is only 1.1 mi away and don't worry about running late to catch the ferry since the Oak Bluffs ferry terminal is only 1.4mi away. By staying at this property you will enjoy the modern comforts of home whilst being whisked away by the charm of the vineyard. OPEN FOR 2024 BOOKINGS!

63 Tradewinds Rd.

This beautiful newly built home was designed for a relaxing getaway in the beautiful nature of Martha's Vineyard. The raw materials here bring the beauty of nature inside. A mix of artistic details create a peaceful environment for your vacation. The first floor holds a bedroom and the bathroom along with the living area and kitchen. The second floor offers a gorgeous expansive open loft with a queen sized bed. Right next door is a community pool.

37 Stoney Hill Lane

NEW PROPERTY!!!!
SO CLOSE TO TOWN! If you are searching for a place that accommodates your group while staying close to Oak Bluffs town center, then search no further. Your guests will have a choice of two first floor bedrooms, and 3 upstairs bedrooms including a master suite that has its own private seating area. This property offers 3 full bathrooms and one outdoor shower. The kitchen offers high end appliances to create the ultimate entertaining experience. Skylights are perfectly placed to bring in plenty of natural light. The expansive gorgeously manicured lawn comes with a play-set to keep the kids happy and busy. This property is set in the historic, favored neighborhood of East Chop which offers privacy and tranquility while still being a stones throw away from town center and the famous Oak Bluffs town beach also known as the Inkwell beach. East Chop also offers its own secluded beach many locals are familiar with. Bring your pet if you'd like because this property is also pet friendly. This is your new summer rental to return to year after year. INQUIRE NOW!

60 Monahegan Ave

Ready to book 2025!

This stunning 5-bedroom, 4,5-bathroom home in Katama, Edgartown boasts an abundance of natural light, creating an inviting and airy atmosphere. With spacious rooms, modern amenities, and a picturesque setting, it offers the perfect blend of comfort and elegance.
Enjoy the serene surroundings and luxuries living in this beautiful property.

4 Steven-John

READY FOR 2025 BOOKINGS

Welcome to the Falu House, a European-inspired A-Frame cottage in walking distance to the Lagoon and close to the Oak Bluffs town center!

This cozy home boasts two bedrooms and bathrooms, a perfect getaway for a memorable family vacation. The cottage has recently been renovated to create a comfortable, laid back vacation retreat. The open-concept living area is ideal for relaxing after a day of exploring the island, while a fully equipped kitchen invites you to whip up delicious meals for family and friends. The free-standing gas stove provides warmth and coziness during cooler nights. And with new air-conditioning in the living and bedroom spaces, you will stay comfortable during those warm summer days. 

Outside you will find a spacious deck overlooking the wooded surroundings--the perfect spot to savor your morning coffee. Use the charcoal BBQ grill to entertain legendary summer gatherings, or enjoy a glass wine by the fire pit on the newly added garden patio. A spacious outdoor shower completes your Vineyard experience! 

Both bedrooms offer comfortable queen-sized beds with premium cotton sheets. The property provides linens and towels and is pet- and infant-friendly (we offer a travel crib, high chair, and baby bath upon request). We also provide beach gear, including beach towels, a cooler, beach chairs, and a beach umbrella. 

The property is a five-minute walk to Lagoon pond where you can launch your kayak or paddle board and enjoy the sunset. The MV Sail Camp is also in walking-distance. Oak Bluffs Town Center is a 20-minute walk or 4-minute drive. The neighborhood is peaceful and quiet while close to all amenities as well as the ferry terminals in Vineyard Haven and Oak Bluffs.

Conveniently located in Oak Bluffs this house is a perfect home base for your Martha's Vineyard adventure.

Property provides linens and towels and is pet friendly.

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