Farm Pond Rentals
From $246 per night (USD)VRBO
Martha’s Vineyard studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Studio apartment on highly sought resort island of Martha’s Vineyard. 500 square feet with private entrance, bathroom, ...
From $246 per night (USD)VRBO
From $723 per night (USD)VRBO
Charming Oak Bluffs Retreat – Walk to Town, Harbor & More
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Just outside downtown Oak Bluffs, this 3-bedroom, 2.5-bath home features Central AC and an open layout ideal for gatheri ...
From $723 per night (USD)VRBO
From $961 per night (USD)VRBO
Historical house with wraparound porch, modern updates, enclosed yard, & W/D
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Victorian by the Sea Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $961 per night (USD)VRBO
From $526 per night (USD)Expedia
Inviting, two-story home with a large yard, sunroom, balcony, & washer/dryer
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Gingerbread Dream Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $526 per night (USD)Expedia
From $565 per night (USD)VRBO
Family-built Oak Bluffs property in a wonderful location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Frazier Circle, Unit 1 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $565 per night (USD)VRBO
From $1214 per night (USD)Expedia
Family-built Oak Bluffs property in a great location with kitchens & hot tub
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Frazier Circle Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1214 per night (USD)Expedia
From $726 per night (USD)VRBO
Family-built Oak Bluffs property in a wonderful location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Frazier Circle, Unit 2 Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter ...
From $726 per night (USD)VRBO
From $871 per night (USD)Expedia
Spacious home in central location with beautiful patio, pool table, W/D, & AC
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Bird Street Breeze Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $871 per night (USD)Expedia
From $830 per night (USD)VRBO
New 2 min from Circuit ave
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
* new for 2025: Gameroom with pool table and ping pong table. * Welcome to this beautifully renovated home, located wit ...
From $830 per night (USD)VRBO
From $572 per night (USD)Expedia
Charming cottage near the beach with a furnished deck, yard, & washer/dryer
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Birds of Paradise Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $572 per night (USD)Expedia
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Cute 4-BR House within walking distance of Circuit Avenue
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
It is all about location! Leave the car at the house, and walk right into town. This 4 bedroom, 2 bath home features a l ...
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From $348 per night (USD)VRBO
Tree Top Suite Get-Away
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Our beautiful suite has a private entrance, is a walk down an old fashioned dirt road to a private beach and also right ...
From $348 per night (USD)VRBO
From $1502 per night (USD)VRBO
** Vineyard Vacation Retreat ** with HOT TUB
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Gated 2br house with lots of different places to lounge and relax. Drive through the 10’ granite gate onto the shell dri ...
From $1502 per night (USD)VRBO
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Secluded but not Isolated home for all to enjoy
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
A lovely contemporary cape in East Chop with 3 bedrooms, loft & 2 full baths. High ceilings & skylights. A 1/2 mile walk ...
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3 BR cozy Vineyard Vacation Apartment
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
3 BR apartment located on Circuit Ave walking distance to town. This unit feels like its own house. The kitchen and livi ...
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From $1512 per night (USD)Expedia
**Vineyard Vacation Retreat** -3 BR
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Just a stone's throw from Oak Bluffs and it's beaches, this chic 3 bedroom home provides comfort and privacy. The large ...
From $1512 per night (USD)Expedia
From $620 per night (USD)VRBO
Spacious colonial home close to town with AC, porches, & W/D
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Seabreeze Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $620 per night (USD)VRBO
From $366 per night (USD)Expedia
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Book your next East Coast escape at this Oak Bluffs vacation rental! Conveniently located near downtown Oak Bluffs, this ...
From $366 per night (USD)Expedia
From $955 per night (USD)VRBO
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 $955 per night (USD)VRBO
From $1097 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 $1097 per night (USD)VRBO
From $585 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 $585 per night (USD)VRBO
From $1862 per night (USD)Expedia
\"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 $1862 per night (USD)Expedia
From $2327 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 $2327 per night (USD)VRBO
From $518 per night (USD)VRBO
September 2025 Available! 6 Beds! Near Ocean Park, Inkwell, Ferry, Flying Horses
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
6 Bedrooms with incredible location will comfortably allow your family to vacation in the best part of Oak Bluffs. The l ...
From $518 per night (USD)VRBO
From $263 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 $263 per night (USD)VRBO
From $947 per night (USD)VRBO
Inca Gardens Apt. New To Market - Lg Patio - Pets
- Bedrooms:
- 1
- Bathrooms:
- 3
- 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 $947 per night (USD)VRBO
From $369 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 $369 per night (USD)VRBO
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Luxury Loft Historic Center Oak Bluffs
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 13
This is a wonderfully designed contemporary loft space that is both chic and comfortable. The couches and chairs are do ...
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GingerBread Cottage at Oak Bluffs
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Resort may charge damage deposit fees, cleaning fees, activities fees, and applicable Resort lodging taxes. Intimate Ho ...
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Remodeled and historic, beautiful Oak Bluffs home. Walk to Town and Ferry.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This is a beautifully remodeled, and meticulously maintained house in Cottage City. The property is a short walk to town ...
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