Lakeside Park Rentals
From $611 per night (USD)VRBO
Inviting, two-story home with a large yard, sunroom, balcony, & washer\/dryer
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Gingerbread Dream Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $611 per night (USD)VRBO
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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 ...
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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 ...
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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 ...
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From $1035 per night (USD)VRBO
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 $1035 per night (USD)VRBO
From $884 per night (USD)Expedia
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 $884 per night (USD)Expedia
From $643 per night (USD)VRBO
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 $643 per night (USD)VRBO
From $1374 per night (USD)Expedia
Vineyard Social-Spacious 5BR Home in Oak Bluffs
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Experience comfort and style in this newly completed 5-bedroom home just 1 mile from downtown OB. The home features fant ...
From $1374 per night (USD)Expedia
From $436 per night (USD)VRBO
Martha's Vineyard Home: Walk to Oak Bluffs Beach!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Book your next East Coast escape at this Oak Bluffs vacation rental! Conveniently located near downtown Oak Bluffs, this ...
From $436 per night (USD)VRBO
From $597 per night (USD)Expedia
September 2025 Available! 6 Beds! Near Ocean Park, Inkwell, Ferry, Flying Horses
- Bedrooms:
- 3
- 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 $597 per night (USD)Expedia
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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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From $586 per night (USD)Expedia
Perfect location! By Beach, Harbor & Town! Gorgeous Gingerbread Upstairs Aptmt
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
July and August: Turnover day is generally Friday. This lovely, in-town, impeccably renovated 1800's historic Oak Bluff ...
From $586 per night (USD)Expedia
From $2169 per night (USD)VRBO
Waterfront House On Oak Bluffs Harbor
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Rarely available, large 5 bedroom home with 2 bathrooms and an outside shower right on Oak Bluffs Harbor. Great for kids ...
From $2169 per night (USD)VRBO
From $598 per night (USD)Expedia
Oak Bluffs Retreat - The perfect getaway!
- Bedrooms:
- 3
- 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 $598 per night (USD)Expedia
From $1364 per night (USD)VRBO
\"The Carousel House\" - Ocean Park - Featured in New York Times
- Bedrooms:
- 3
- Bathrooms:
- 7
- 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 $1364 per night (USD)VRBO
From $2170 per night (USD)Expedia
Relaxing Beach Front Home
- Bedrooms:
- 4
- 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 $2170 per night (USD)Expedia
From $1224 per night (USD)VRBO
Big Beach House - Ocean Views!
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 12
Original 1900 Victorian home, updated in 2006, located in the historic Copeland District just one block from the beach. ...
From $1224 per night (USD)VRBO
From $322 per night (USD)Expedia
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 $322 per night (USD)Expedia
From $448 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 $448 per night (USD)VRBO
From $2425 per night (USD)VRBO
Fabulous Waterfront 3-Bedroom Martha's Vineyard Cottage
- Bedrooms:
- 2
- 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 $2425 per night (USD)VRBO
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Remodeled and historic, beautiful Oak Bluffs home. Walk to Town and Ferry.
- Bedrooms:
- 4
- 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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From $908 per night (USD)Expedia
Luxury Loft Historic Center Oak Bluffs
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 13
This is a wonderfully designed contemporary loft space that is both chic and comfortable. The couches and chairs are do ...
From $908 per night (USD)Expedia