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Search results; Over 1,000 homes in Oak Bluffs

Guest favorite
Home in Oak Bluffs
Renovated with a fire pit and deck
3 bedrooms, 4 beds, 2 private baths
Aug 31 – Sep 5
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4.78 out of 5 average rating, 137 reviews
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
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
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
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
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
Post-and-beam barn near the beach
4.94 out of 5 average rating, 519 reviews, 2 beds, 1 bath
Sep 28 – Oct 3
Guest favorite
Cottage in Oak Bluffs
Vaulted ceilings, 5-minute walk to town
4.95 out of 5 average rating, 198 reviews, 1 bedroom, 2 beds, 1.5 baths
Sep 13 – 18
Guest favorite
Home in Oak Bluffs
1800s Gingerbread cottage near the beach
4.92 out of 5 average rating, 211 reviews, 3 bedrooms, 6 beds, 1 bath
Sep 20 – 25
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
Room in Oak Bluffs
Ocean and park views from the porch
4.99 out of 5 average rating, 228 reviews, 1 double bed, 1 bath
Nov 22 – 27
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
Room in Tisbury
Harbor views, 2 blocks from the ferry
4.94 out of 5 average rating, 139 reviews, 1 queen bed, 1 bath
Sep 20 – 25
Superhost
Room in Oak Bluffs
Private entrance, walk to the beach
1 double bed, 1 bath
Sep 13 – 18
Home in Oak Bluffs
Lagoon sunsets from the waterfront deck
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2 baths
Sep 27 – Oct 2
Guest favorite
Home in Tisbury
Wood-fired pizza oven and a fire pit
4.93 out of 5 average rating, 188 reviews, 3 bedrooms, 5 beds, 2 baths
Oct 18 – 23
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
Rooms in Edgartown
1800s whaling captain’s home, walkable Edgartown
4.85 out of 5 average rating, 563 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 27 – Oct 2
Top guest favorite
Home in Oak Bluffs
French country chic on Martha’s Vineyard
4.96 out of 5 average rating, 131 reviews, 3 bedrooms, 3 beds, 2 baths
Sep 8 – 13