No. 01
Blissful Island Haven
House
4 bedroom
sleeps 4
Beachfront
Blissful Island Haven offers a spacious holiday home in Oak Bluffs, United States.
The Vineyard's 100 square miles cover six towns, each with its own character. Edgartown for captains' houses, Chilmark for cliffs, Oak Bluffs for gingerbread cottages, Aquinnah for red clay bluffs. Rentals concentrate in July-August; May and September are cheaper and quieter.
StateMA
Peak seasonJuly to August
Best forWaterfront stays
Featured9 rentals
The curated list · 9 rentals
Where we would stay in Oak Bluffs, Martha's Vineyard.
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No. 02
Island Dream
Vacation Home
4 bedroom
sleeps 8
Sea view
Island Dream in Oak Bluffs offers a spacious holiday home with four bedrooms and five bathrooms.
No. 03
Seabreeze Retreat
House
4 bedroom
sleeps 8
Ocean View
Spacious Accommodations in Oak Bluffs with four bedrooms and two bathrooms.
No. 04
Winthrop Cottage
Vacation Home
3 bedroom
sleeps 6
Steps to Beach
Spacious Accommodations: Winthrop Cottage in Oak Bluffs offers a spacious holiday home with three bedrooms and one bathroom.
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No. 05
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
Apartment
2 bedroom
sleeps 4
Beachfront
Beachfront location with direct access to Inkwell Beach.
No. 06
Heart of Oak Bluffs Walk to Beach & Ferries
Vacation Home
2 bedroom
sleeps 4
Steps to Beach
The entire place is yours with a private kitchen and city views.
No. 07
The Pinkletink
Holiday home
1 bedroom
sleeps 4
Oceanfront
Comfortable Living: The Pinkletink in Oak Bluffs offers a holiday home with one bedroom and a living room.
No. 08
Capricorn House
Oceanfront
Housed in a historic building, Capricorn House features accommodations with a terrace and free Wifi in Oak Bluffs, a 1-minute walk from Oak Bluffs Town Beach.
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9
curated rentals in Oak Bluffs, Martha's Vineyard
No. 09
Breezy Oak Bluffs Condo - Steps to Inkwell Beach!
Oceanfront
Breezy Oak Bluffs Condo - Steps to Inkwell Beach! is located in Oak Bluffs, just a few steps from Oak Bluffs Town Beach and 5.9 miles from Edgartown Lighthouse.
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