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Search results; Over 1,000 homes in Oak Bluffs

Top guest favorite
Bed and breakfast
This Oak Bluffs suite gives you a private entrance, king bed, and breakfast on the deck
1 bedroom, 1 bed, 1 private bath
Aug 28 – Sep 2
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5.0 out of 5 average rating, 37 reviews
Top guest favorite
This newly built rustic cabin in Oak Bluffs gives you a private entrance and porch
5.0 out of 5 average rating, 10 reviews, 1 bedroom, 1 bed, 1 bath
Sep 13 – 18
Top guest favorite
This Oak Bluffs suite gives you a private deck and entrance near a golf course
4.98 out of 5 average rating, 202 reviews, 1 bedroom, 1 bed, 1 bath
Aug 20 – 25
Featured hotel
Room in Oak Bluffs
Queen
5.0 out of 5 average rating, 3 reviews, 1 queen bed, 1 bath
Sep 29 – Oct 4
Guest favorite
This Oak Bluffs post-and-beam barn studio gives you a private entrance and patio
4.94 out of 5 average rating, 519 reviews, 2 beds, 1 bath
Sep 28 – Oct 3
Guest favorite
This Oak Bluffs apartment puts you right on the bike path with a private entrance
4.95 out of 5 average rating, 431 reviews, 2 bedrooms, 2 beds, 1 bath
Oct 18 – 23
Top guest favorite
Stargaze through the circular skylight of this Oak Bluffs luxury yurt
4.93 out of 5 average rating, 316 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 19 – 24
Guest favorite
This 1800s gingerbread cottage in Oak Bluffs puts you steps from Circuit Ave
4.92 out of 5 average rating, 211 reviews, 3 bedrooms, 6 beds, 1 bath
Sep 20 – 25
Top guest favorite
Private room
Look out over the ocean from the porch of this Oak Bluffs Victorian suite
4.99 out of 5 average rating, 228 reviews, 1 double bed, 1 bath
Nov 22 – 27
Guest favorite
This renovated Oak Bluffs home gives you a wraparound porch over an acre of lawn
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 1 bath
Aug 26 – 31
Top guest favorite
Private room
Harbor views greet you at this historic Tisbury room, 2 blocks from the ferry
4.94 out of 5 average rating, 139 reviews, 1 queen bed, 1 bath
Sep 20 – 25
Wake to Lagoon views at this Oak Bluffs waterfront house with a guest cottage
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2 baths
Sep 27 – Oct 2
Guest favorite
This Vineyard Haven house gives you a wood-fired pizza oven, fire pit, and two decks
4.93 out of 5 average rating, 188 reviews, 3 bedrooms, 5 beds, 2 baths
Oct 18 – 23
This gingerbread Victorian in Oak Bluffs puts you a walk from the beach
New place to stay, 4 bedrooms, 5 beds, 3.5 baths
Sep 27 – Oct 2
Superhost
Private room
This Oak Bluffs private room gives you your own entrance and outdoor shower
1 double bed, 1 bath
Sep 13 – 18
Top guest favorite
This Oak Bluffs house gives you French country charm and a spacious backyard
4.96 out of 5 average rating, 131 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 8 – 13
Top guest favorite
Perched on a bluff, this Oak Bluffs cottage gives you panoramic lagoon views and private beach access
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 2 baths
Oct 3 – 8
Guest favorite
This bright contemporary Oak Bluffs home gives you deck space on a wooded cul-de-sac
4.79 out of 5 average rating, 259 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 26 – Oct 1
Top guest favorite
Bed and breakfast
A 200-year-old captain’s home in Edgartown where you’ll have a private suite
4.85 out of 5 average rating, 563 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 27 – Oct 2