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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Cottage in Oak Bluffs
East Chop Cottage - walk to lighthouse & beach!
1 bedroom, 1 bed, 0.5 private bathroom
25–30 Aug
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4.9 out of 5 average rating, 143 reviews
Featured hotel
Hotel in Oak Bluffs
Water view double queen
1 bedroom, 2 queen beds
16–21 Sept
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds
18–23 Oct
4.95 out of 5 average rating, 423 reviews
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds
16–21 Oct
4.93 out of 5 average rating, 308 reviews
Guest favourite
Cottage in Oak Bluffs
Oak Bluffs, Martha's Vineyard; Gingerbread House
3 bedrooms, 4 beds
12–19 Jul
4.88 out of 5 average rating, 16 reviews
Top guest favourite
Guest house in Oak Bluffs
Oak bluffs cottage Perfect place to honeymoon!
2 bedrooms, 2 beds
18–23 Oct
4.97 out of 5 average rating, 132 reviews
Cabin in Oak Bluffs
Newly built cabin walking distance from Oak Bluffs
1 bedroom, 1 bed
21–26 Jul
New place to stay
Guest favourite
Home in Oak Bluffs
Studio apt in newly built barn
2 beds
27 Sept – 2 Oct
4.94 out of 5 average rating, 511 reviews
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage - Sleeps 8
3 bedrooms, 4 beds
16–21 Jul
New place to stay
Guest favourite
Room in Oak Bluffs
Oak Bluffs/ Harbor Views/ Queen Bed/ In Town
1 queen bed
30 Aug – 4 Sept
4.9 out of 5 average rating, 104 reviews
Guest favourite
Guest house in Oak Bluffs
Sweet Summer Cottage
1 bedroom, 1 queen bed
26–31 Jul
4.92 out of 5 average rating, 65 reviews
Superhost
Home in Oak Bluffs
Quintessential 1920s renovated bungalow new 2026!
2 bedrooms, 2 beds
23–28 Jul
New place to stay
Top guest favourite
Flat in Oak Bluffs
14A Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds
20–25 Jul
4.97 out of 5 average rating, 29 reviews
Top guest favourite
Flat in Oak Bluffs
Beautiful private apartment walk to everything!
1 bedroom, 2 beds
18–23 Jul
4.95 out of 5 average rating, 194 reviews
Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed
12–17 Jul
4.98 out of 5 average rating, 196 reviews
Top guest favourite
Flat in Oak Bluffs
Town/Beach: Vineyard Vacation Houses welcomes you!
1 bedroom, 2 beds
15–20 Oct
4.89 out of 5 average rating, 303 reviews
Top guest favourite
Room in Tisbury
Historic Captain's House. Walk to town and ferry
2 beds
29 Sept – 4 Oct
4.99 out of 5 average rating, 154 reviews
Guest favourite
Home in Oak Bluffs
Oak Bluffs | A/C, Outdoor Shower, Walk to Town
3 bedrooms, 6 beds
10–15 Jul
5.0 out of 5 average rating, 7 reviews
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds
17–22 Jul
New place to stay