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Search results; Over 1,000 homes in Oak Bluffs

Guest favorite
This Oak Bluffs house on Lagoon Pond gives you a pizza oven and private beach
5 bedrooms, 6 beds, 2 private baths
Sep 13 – 18
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4.94 out of 5 average rating, 66 reviews
Top guest favorite
This Oak Bluffs house gives you a private pool and backyard beach access
4.93 out of 5 average rating, 221 reviews, 4 bedrooms, 5 beds, 5.5 baths
Oct 4 – 9
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 23 – 28
Top guest favorite
This Oak Bluffs house puts you half a mile from Eastville Beach with a big back deck
4.98 out of 5 average rating, 58 reviews, 3 bedrooms, 5 beds, 2.5 baths
Oct 16 – 21
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
Top guest favorite
This brand new Oak Bluffs home gives you direct lagoon access and a fire pit
4.98 out of 5 average rating, 54 reviews, 3 bedrooms, 3 beds, 3 baths
Sep 27 – Oct 2
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
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
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
Guest favorite
Cathedral ceilings and hardwood floors greet you at this new Oak Bluffs home
4.98 out of 5 average rating, 86 reviews, 3 bedrooms, 6 beds, 2.5 baths
Aug 31 – Sep 5
Top guest favorite
Sip wine on the deck at this Tisbury cottage with a private backyard
5.0 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 22 – 29
This quiet Oak Bluffs guesthouse gives you a fire pit and outdoor shower
4.91 out of 5 average rating, 11 reviews, 1 bedroom, 2 beds, 1 bath
Aug 30 – Sep 4
This Oak Bluffs home puts you near Town Beach with a private backyard
3 bedrooms, 3 beds, 1 bath
Aug 22 – 27
Guest favorite
This secluded Oak Bluffs home gives you a fire pit, hammock, and lush gardens
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 6 beds, 3 baths
Aug 23 – 28
Guest favorite
This newly built Oak Bluffs home gives you a private yard, patio BBQ, and bikes
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1.5 baths
Aug 29 – Sep 3
Top guest favorite
This brand-new Oak Bluffs apartment puts you a short walk from Inkwell Beach
5.0 out of 5 average rating, 28 reviews, 1 bedroom, 2 beds, 1 bath
Aug 25 – 30
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
Guest favorite
High vaulted ceilings greet you at this Oak Bluffs cottage with a patio and grill
4.95 out of 5 average rating, 198 reviews, 1 bedroom, 2 beds, 1.5 baths
Sep 13 – 18