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Search results; Over 1,000 homes in Oak Bluffs

Top guest favorite
Apartment in Oak Bluffs
Historic 1862 building in Oak Bluffs’ heart
2 bedrooms, 4 beds, 1 private bath
Sep 20 – 25
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4.92 out of 5 average rating, 133 reviews
Top guest favorite
Home in Oak Bluffs
Pool and private beach on the Vineyard
4.93 out of 5 average rating, 221 reviews, 4 bedrooms, 5 beds, 5.5 baths
Oct 4 – 9
Top guest favorite
Guest suite in Oak Bluffs
Private deck minutes from the beach
4.98 out of 5 average rating, 202 reviews, 1 bedroom, 1 bed, 1 bath
Aug 23 – 28
Top guest favorite
Cabin in Oak Bluffs
Newly built with a front porch
5.0 out of 5 average rating, 10 reviews, 1 bedroom, 1 bed, 1 bath
Sep 13 – 18
Top guest favorite
Home in Oak Bluffs
Half mile from the beach, big deck
4.98 out of 5 average rating, 58 reviews, 3 bedrooms, 5 beds, 2.5 baths
Oct 16 – 21
Home in Oak Bluffs
Gingerbread Victorian, walk to the beach
New place to stay, 4 bedrooms, 5 beds, 3.5 baths
Sep 27 – Oct 2
Top guest favorite
Cottage in Oak Bluffs
Private beach on a 25-foot bluff
5.0 out of 5 average rating, 12 reviews, 4 bedrooms, 5 beds, 2 baths
Oct 3 – 8
Top guest favorite
Home in Oak Bluffs
Luxury yurt with a circular skylight
4.93 out of 5 average rating, 316 reviews, 2 bedrooms, 3 beds, 1 bath
Oct 19 – 24
Guesthouse in Oak Bluffs
Quiet neighborhood with a fire pit
4.91 out of 5 average rating, 11 reviews, 1 bedroom, 2 beds, 1 bath
Aug 30 – Sep 4
Top guest favorite
Cottage in Tisbury
Private backyard, blocks from the beach
5.0 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 22 – 29
Top guest favorite
Home in Oak Bluffs
Brand-new home with direct lagoon access
4.98 out of 5 average rating, 54 reviews, 3 bedrooms, 3 beds, 3 baths
Sep 27 – Oct 2
Guest favorite
Guest suite in Oak Bluffs
Private entrance on the bike path
4.95 out of 5 average rating, 431 reviews, 2 bedrooms, 2 beds, 1 bath
Oct 18 – 23
Guest favorite
Home in Oak Bluffs
New build with cathedral ceilings and deck
4.98 out of 5 average rating, 86 reviews, 3 bedrooms, 6 beds, 2.5 baths
Aug 31 – Sep 5
Top guest favorite
Apartment in Oak Bluffs
Brand-new luxury, blocks from the beach
5.0 out of 5 average rating, 28 reviews, 1 bedroom, 2 beds, 1 bath
Aug 25 – 30
Guest favorite
Home in Oak Bluffs
Newly built with bikes and a BBQ
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1.5 baths
Aug 29 – Sep 3
Guest favorite
Home in Oak Bluffs
Wraparound porch on a full acre
5.0 out of 5 average rating, 8 reviews, 3 bedrooms, 3 beds, 1 bath
Aug 26 – 31
Top guest favorite
Apartment in Oak Bluffs
Vaulted ceilings, 5-minute walk to beaches
4.95 out of 5 average rating, 201 reviews, 1 bedroom, 2 beds, 1 bath
Aug 30 – Sep 4
Home in Oak Bluffs
Walk to Circuit Ave and Town Beach
3 bedrooms, 3 beds, 1 bath
Aug 22 – 27
Guest favorite
Home in Oak Bluffs
Secluded lot with a fire pit
5.0 out of 5 average rating, 5 reviews, 4 bedrooms, 6 beds, 3 baths
Aug 23 – 28