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Search results; Over 1,000 homes in Oak Bluffs

Guest favorite
Condo in Oak Bluffs
113B Cutest! Walk to Beach, Town and Harbor!
1 bedroom, 1 bed, 1 private bath
Aug 26 – 31
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4.9 out of 5 average rating, 271 reviews
Top guest favorite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4 bedrooms, 5 beds, 5.5 baths
Oct 4 – 9
4.93 out of 5 average rating, 221 reviews
Top guest favorite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bath
Sep 13 – 18
5.0 out of 5 average rating, 10 reviews
Top guest favorite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed, 1 bath
Aug 23 – 28
4.98 out of 5 average rating, 201 reviews
Top guest favorite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds, 2.5 baths
Oct 16 – 21
4.98 out of 5 average rating, 56 reviews
Top guest favorite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds, 2 baths
Oct 3 – 8
5.0 out of 5 average rating, 12 reviews
Top guest favorite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bath
Oct 19 – 24
4.93 out of 5 average rating, 316 reviews
Guest favorite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds, 1 bath
Oct 18 – 23
4.95 out of 5 average rating, 428 reviews
Guest favorite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
3 bedrooms, 6 beds, 2.5 baths
Aug 31 – Sep 5
4.98 out of 5 average rating, 86 reviews
Top guest favorite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds, 3 baths
Sep 27 – Oct 2
4.98 out of 5 average rating, 54 reviews
Guest favorite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds, 1 bath
Sep 20 – 25
4.92 out of 5 average rating, 211 reviews
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds, 3.5 baths
Sep 27 – Oct 2
New place to stay
Home in Oak Bluffs
Vineyard Family Home
3 bedrooms, 3 beds, 1 bath
Aug 22 – 27
Top guest favorite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom, 2 beds, 1.5 baths
Sep 18 – 23
4.97 out of 5 average rating, 186 reviews
Guest favorite
Cottage in Oak Bluffs
#Islandbeachrose. Walk To Beach and Town!
4 bedrooms, 6 beds, 2 baths
Sep 6 – 13
4.92 out of 5 average rating, 26 reviews
Top guest favorite
Apartment in Oak Bluffs
14D Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bath
Aug 24 – 29
4.95 out of 5 average rating, 37 reviews
Guest favorite
Home in Oak Bluffs
Sunny 3-bed close to beach and town
3 bedrooms, 3 beds, 2 baths
Aug 22 – 27
4.91 out of 5 average rating, 33 reviews
Top guest favorite
Cottage in Tisbury
Island Charmer!
2 bedrooms, 2 beds, 1 bath
Aug 22 – 29
5.0 out of 5 average rating, 40 reviews
Top guest favorite
Home in Oak Bluffs
The Lighthouse
3 bedrooms, 6 beds, 2 baths
Sep 6 – 11
4.94 out of 5 average rating, 158 reviews