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From $1180 per night (USD)
VRBO
Charming 4-bedroom home in marvelous Tisbury walking distance to shops and ferry
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to Lake Street Haven, a beautifully decorated 4 bedroom, 3 bathroom private home located in the heart of Vineyard ...
From $1180 per night (USD)
VRBO
From $951 per night (USD)
Expedia
Charming, Victorian in East Chop
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Relax with the whole family at this peaceful place to stay. Ideally located in East Chop, in walking distance to the B ...
From $951 per night (USD)
Expedia
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VRBO
Ocean View, Walk to Beach, Dog Friendly
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Beautiful Aquinnah Home: Ocean View, Walk to Beach Oceanview Escape Near Lobsterville Beach | Dog Friendly + Spacious D ...
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VRBO
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Expedia
Historic 11 room Full House Rental in Oak Bluffs walking distance to beach
Bedrooms:
7
Bathrooms:
12
Sleeps:
20
Nestled in the heart of Oak Bluffs, this expansive and beautifully designed home offers the ultimate getaway. Just a sho ...
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Expedia
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VRBO
Quintessential Martha's Vineyard cottage with yard/patio - walk to Inkwell Beach
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Summary: The Pinkletink The Space: Full of classic island charm and beautiful views of the surrounding brush and we ...
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VRBO
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Expedia
Enchanting bungalow with golf nearby, full kitchen, central AC, & washer/dryer
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Summary: East Chop 90 The Space: Welcome to coastal living on the East Chop, a perfect place to bring loved ones fo ...
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Expedia
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VRBO
Split-Level, Family-Friendly Home w/ a Rear Deck, Gas Grill, Free WiFi, & W/D
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Summer Daze The Space: This two-level, family-friendly home welcomes you with open arms, inviting you to s ...
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VRBO
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Expedia
Edgartown Trumpet Vine: Walk to Everything
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
You will feel right at home in this owner/architect designed 2-bedroom, 1 ½-bath house with original art in the heart of ...
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Expedia
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VRBO
Coastal Comfort in Vineyard Haven: Newly Renovate Home: Sleeps 8
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to our beautifully renovated Vineyard Haven retreat at 14 Uncatena Terrace, with access to a private association ...
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VRBO
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VRBO
BLUFF BREEZE - Timeless 6BR East Chop Compound
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Summary: Nestled in the heart of East Chop, this timeless Oak Bluffs retreat offers an idyllic blend of nostalgic islan ...
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VRBO
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VRBO
Charming Waterfront 2-bedroom house in beautiful Vineyard Haven
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Nestled on a peaceful road in Vineyard Haven, this marvelous house offers a cozy waterfront retreat for up to 6 guests. ...
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VRBO
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VRBO
Updated Coastal Oak Bluffs Retreat - AC, Patio, Walk to Town & Beach
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
For offseason rentals, (fall and winter 2026-2027), please inquire for the dates you are interested in. We will respond ...
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VRBO
From $2180 per night (USD)
VRBO
Downtown Edgartown - Loved Family home -Walk to Town and Beaches
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Our home is a well loved Vineyard family home. Located just .2 mile from Main Street down town Edgartown on a quiet, pr ...
From $2180 per night (USD)
VRBO
From $319 per night (USD)
VRBO
Spacious 1 Bedroom Apt - 3 min Walk to the Beach!
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
A perfect place for 1-4 people to stay! You will have plenty of room, shared use of a grill, backyard, and outdoor dinin ...
From $319 per night (USD)
VRBO
From $1212 per night (USD)
VRBO
Bright, fresh Edgartown saltbox
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Recently refreshed and refurnished salt box. Home is steps away from the tennis courts, walking distance to Morning Glor ...
From $1212 per night (USD)
VRBO
From $909 per night (USD)
VRBO
5BR in West Tisbury village with private beach access
Bedrooms:
1
Bathrooms:
5
Sleeps:
9
Spacious house in heart of historic West Tisbury, under 5 minutes walk from: Library, playground, Alley's, 7a, Grange Ha ...
From $909 per night (USD)
VRBO
From $333 per night (USD)
VRBO
Up-Island Treehouse with Roofdeck and Waterviews
Bedrooms:
1
Bathrooms:
2
Sleeps:
3
Welcome to our getaway. The Up-Island Treehouse offers an open, light-filled and breezy spot on the western tip of Marth ...
From $333 per night (USD)
VRBO
From $606 per night (USD)
VRBO
Chic Luxury Cottage In Edgartown Village
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
POINT B EXCLUSIVE - Tucked away on a quiet village lane, this renovated classic cottage has stylish details throughout. ...
From $606 per night (USD)
VRBO
From $1279 per night (USD)
VRBO
Classic Modern House on its Own Point of Land with Astounding Views
Bedrooms:
1
Bathrooms:
5
Sleeps:
11
Designed by a student of the famous architect Walter Gropius, our house was built in 1949. The house is open and light, ...
From $1279 per night (USD)
VRBO
From $2141 per night (USD)
VRBO
3 bedroom home in Edgartown, steps from bike path and island bus.
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Enjoy this 2200 sq foot Edgartown home . 5 Complimentary bikes to use during your stay. Everything in this Vineyard home ...
From $2141 per night (USD)
VRBO
From $575 per night (USD)
VRBO
Edgartown Pied-à-Terre
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
IMPORTANT: PLEASE SEND AN INQUIRY (click on contact host) PRIOR TO SENDING A BOOKING REQUEST. Booking requests sent with ...
From $575 per night (USD)
VRBO
From $4431 per night (USD)
VRBO
Waterfront House On Oak Bluffs Harbor
Bedrooms:
1
Bathrooms:
5
Sleeps:
10
Rarely available, large 5 bedroom home with 2 bathrooms and an outside shower right on Oak Bluffs Harbor. Great for fami ...
From $4431 per night (USD)
VRBO
From $8713 per night (USD)
VRBO
Perfect Luxury Vineyard Retreat
Bedrooms:
4
Bathrooms:
6
Sleeps:
15
Sit back and relax in this chic, recently renovated and expanded, beautifully furnished six-bedroom home overlooking the ...
From $8713 per night (USD)
VRBO
From $753 per night (USD)
VRBO
Edgartown/Katama Newly Renovated Vineyard Escape
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Recently renovated wonderful 3 bedroom, 2 bath Vineyard house. Our guests will be delighted by the clean, beach vibe r ...
From $753 per night (USD)
VRBO
$\The Carousel House\ - Ocean Park - Featured in New York Times$
From $2050 per night (USD)
VRBO
\"The Carousel House\" - Ocean Park - Featured in New York Times
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
This house, built in 1865, was featured in the New York Times article on Oak Bluffs, 'The President Was Here (Grant, Tha ...
From $2050 per night (USD)
VRBO
From $624 per night (USD)
VRBO
Oak Bluffs Retreat - The perfect getaway!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Six minute drive to beach! This two floor beauty with central AC boasts ample yard space and all the amenities you look ...
From $624 per night (USD)
VRBO
From $2197 per night (USD)
VRBO
Relaxing Beach Front Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
The Perfect Vineyard Vacation: This beautiful beachfront home is on the east side of Lagoon Pond, in the town of Oak Blu ...
From $2197 per night (USD)
VRBO
From $2358 per night (USD)
VRBO
Family Friendly Quiet Neighborhood Heated In-ground Pool SUNDAY CHECKIN
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Cape style home with heated in ground pool located only a 4 minute walk to Sengekontacket Pond where you can kayak or pa ...
From $2358 per night (USD)
VRBO
From $1479 per night (USD)
VRBO
Big Beach House - Ocean Views!
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
Original 1900 Victorian home, updated in 2006, located in the historic Copeland District just one block from the beach. ...
From $1479 per night (USD)
VRBO
From $1560 per night (USD)
VRBO
Charming1700's Edgartown Village Cottage 5 Minute walk to Downtown
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Charming & Historical Circa 1700 Edgartown Village Classic with original pumpkin pine floors throughout. Fuller Street b ...
From $1560 per night (USD)
VRBO
From $1398 per night (USD)
VRBO
Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
A unique opportunity to spend your vacation in peaceful Abel’s Hill in Chilmark. This lovely cottage is located in the h ...
From $1398 per night (USD)
VRBO
From $925 per night (USD)
VRBO
Modern & Spacious Edgartown Home with Pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Enjoy your vacation in this wonderfully charming three bedroom home with an in-ground heated pool. Head to the beach or ...
From $925 per night (USD)
VRBO
From $1268 per night (USD)
VRBO
New King Bed, Studio -Downtown Edgartown
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Incredible location in downtown Edgartown. This remodeled unit is located on the upper level and features a corner posit ...
From $1268 per night (USD)
VRBO
From $409 per night (USD)
VRBO
Walk to Town & Water from your PERFECT SUMMER COTTAGE
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
JULY AND AUGUST: turnover day is Monday ----------------------------- We'd love to welcome you into our lovely 500 sq. f ...
From $409 per night (USD)
VRBO
From $1461 per night (USD)
VRBO
New 4 BR house near center and beaches with bikes
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Renovated 4 bedrooms/2 bathrooms house with a lovely kitchen that includes all the amenities and much more. Large Living ...
From $1461 per night (USD)
VRBO
From $645 per night (USD)
VRBO
Modern Edgartown Retreat - Minutes to Beaches & Town Centers
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Tucked away off Edgartown/Vineyard Haven Road, this stylish, modern home offers the perfect blend of privacy, comfort an ...
From $645 per night (USD)
VRBO
From $894 per night (USD)
VRBO
6 Beds! Walk to Beach, Ferry, Ocean Park and OB!
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Our home with 6 Bedrooms and incredible location will comfortably allow your family to vacation in the best part of Oak ...
From $894 per night (USD)
VRBO
From $877 per night (USD)
VRBO
Centrally located Oak Bluffs property next to Bike Path
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Welcome to our vacation rental in Oak Bluffs, Martha's Vineyard! Lovely home in the sought after Meadow View Farms commu ...
From $877 per night (USD)
VRBO
From $774 per night (USD)
VRBO
Waterfront cottage a short boat ride to the ocean beach
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Our waterfront cottage on Chilmark Pond is a short boat ride to a stunning barrier beach on the Atlantic Ocean. There i ...
From $774 per night (USD)
VRBO
From $3073 per night (USD)
Expedia
Stunning private family home - spectacular sunsets
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Our family home is a 4-acre waterfront paradise with wonderful sunsets. The private location sits between a large wooded ...
From $3073 per night (USD)
Expedia
From $390 per night (USD)
VRBO
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
July and August: Turnover day is generally Friday. This lovely, in-town, impeccably renovated 1800's historic Oak Bluff ...
From $390 per night (USD)
VRBO
From $670 per night (USD)
Expedia
Vineyard Haven Oasis!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This Vineyard Haven Oasis is fully equipped. It’s Centrally Located to Downtown Vineyard Haven, Island attractions, res ...
From $670 per night (USD)
Expedia
From $574 per night (USD)
VRBO
Quiet Edgartown vacation home - 10 minutes from door to beach chair!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This home is equipped with everything you need for a day on South Beach, State Beach or nearby Long Point. Perfect for a ...
From $574 per night (USD)
VRBO
From $1661 per night (USD)
Expedia
Edgartown Village Home w/ Pool. 4bdrm / 3.5bth
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Fully renovated in 2020, this 4 bedroom / 3.5 bath cottage is the perfect spot for fun and relaxation. 0.4 miles to Main ...
From $1661 per night (USD)
Expedia
From $926 per night (USD)
VRBO
Renovated colonial in private Island Grove community
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
**Transferrable Ferry tickets available 6/28-7/5; 7/5-7/12; 8/23-8/30** Spacious Colonial in private Edgartown communit ...
From $926 per night (USD)
VRBO
From $1407 per night (USD)
VRBO
In Town Captain's house
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
An elegant historic Captain’s house 2 blocks to downtown, the ferry, town pier and beach, and restaurants. An expansive ...
From $1407 per night (USD)
VRBO
From $1679 per night (USD)
VRBO
Wintucket Cove Path--On The Great Pond--Boating And Biking! Central A/C
Bedrooms:
4
Bathrooms:
6
Sleeps:
12
Beautiful, large and comfortable Cape farmhouse on 8.8 acres in exclusive Edgartown location on the Great Pond. Walk do ...
From $1679 per night (USD)
VRBO
From $1163 per night (USD)
VRBO
Chilmark two bedroom, one bath cottage with waterfront and private beach
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A wonderful two bedroom cottage nicknamed The Palace ,and it truly is one! on a private estate with private access to th ...
From $1163 per night (USD)
VRBO
From $886 per night (USD)
VRBO
Chilmark pond side cottage with beach access, sweeping views
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Everyday is a beach day! A magical beach retreat cottage at the water's edge, nicknamed Gadget. at Wades Cove at lower ...
From $886 per night (USD)
VRBO
From $1413 per night (USD)
Expedia
NEW! Edgartown 3 BR 2 Bath Newly Remodeled Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Completely renovated home located less than 3 miles from the Edgartown center and conveniently located near bike path a ...
From $1413 per night (USD)
Expedia
From $874 per night (USD)
VRBO
Inca Gardens Apartment w Large Patio and Deck - Pets OK
Bedrooms:
1
Bathrooms:
4
Sleeps:
6
Inca Gardens is a 2nd-floor apartment of a cute house located in a quiet area of Martha's Vineyard between Oak Bluffs an ...
From $874 per night (USD)
VRBO
From $563 per night (USD)
VRBO
Family cottage in Oak Bluffs. Close to town
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Bright cottage for a small family or friends getaway with a large yard for lounging and outdoor dining. One mile from d ...
From $563 per night (USD)
VRBO
From $3407 per night (USD)
VRBO
Modern 6Bed-6Bath New in 2023!
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Full Renovation just completed December 2022 - Very Modern New Kitchen and all Miele new appliances and 40 Bottle Wine F ...
From $3407 per night (USD)
VRBO
From $2735 per night (USD)
VRBO
Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
This quintessential Vineyard cottage was built in the 1920's, and retains most of its original charm and character. Loca ...
From $2735 per night (USD)
VRBO
From $2308 per night (USD)
VRBO
NEW Edgartown Luxury Home with Pool / Walk to Downtown Village
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Brand new house with high-end everything! Gourmet Kitchen-Subzero/Wolf Large bathrooms with two sink vanities 10 foot ...
From $2308 per night (USD)
VRBO
From $1836 per night (USD)
VRBO
East Chop beach house, private beach with sunsets views.
Bedrooms:
3
Bathrooms:
3
Sleeps:
9
Quintessential, beach cottage on East Chop near light house. Water views from almost every window. Beach, boating, wate ...
From $1836 per night (USD)
VRBO
From $775 per night (USD)
VRBO
A View Fit for Royalty! Top Compliments: so clean! fab hot tub! best view!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The reviews say it all. We are a 5-star property because we surprise and delight our renters with not only a great hom ...
From $775 per night (USD)
VRBO
From $902 per night (USD)
Expedia
Luxury Loft Historic Center Oak Bluffs
Bedrooms:
2
Bathrooms:
6
Sleeps:
14
This is a wonderfully designed contemporary loft space that is both chic and comfortable. The couches and chairs are do ...
From $902 per night (USD)
Expedia
From $685 per night (USD)
VRBO
Classic Vineyard Summer Cottage; Private Waterfront Access; Menemsha Pond Views.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Classic Vineyard summer cottage with private waterfront access to cove on Menemsha Pond on 1.5+/- acres within a few min ...
From $685 per night (USD)
VRBO
From $586 per night (USD)
VRBO
Spectacular Martha's Vineyard Island Home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
12
This is our beautiful home on Martha's Vineyard we call Shangri-La! Spectacular setting with a great peaceful view overl ...
From $586 per night (USD)
VRBO
From $1032 per night (USD)
VRBO
Beautiful Oak Bluffs Home, Steps from the Lagoon
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Come enjoy this beautifully designed home. With 3 bedrooms and 3 full bathrooms you will have all the space you need. An ...
From $1032 per night (USD)
VRBO

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Dukes Area Rentals

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Results: 861 Rentals