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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
Beautiful 3 bedroom in Oak Bluffs, walk to beach
3 bedrooms, 6 beds, 2.5 private bathrooms
30 Aug – 4 Sept
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4.82 out of 5 average rating, 128 reviews
Home in Oak Bluffs
Amanda’s Veranda
New place to stay, 4 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
Home in Oak Bluffs
East Chop Oceanview Escape
5.0 out of 5 average rating, 4 reviews, 6 bedrooms, 8 beds, 4.5 bathrooms
21–27 Aug
Home in Oak Bluffs
Adorable Oak Bluffs Gingerbread House
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 5 beds, 2.5 bathrooms
19–26 Jun
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
4.93 out of 5 average rating, 313 reviews, 2 bedrooms, 3 beds, 1 bathroom
19–24 Oct
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 427 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
5.0 out of 5 average rating, 5 reviews, 1 bedroom, 1 bed, 1 bathroom
13–18 Sept
Home in Oak Bluffs
Oak Bluffs Summer Home
New place to stay, 3 bedrooms, 4 beds, 2 bathrooms
22–27 Aug
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
4.95 out of 5 average rating, 213 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
4.8 out of 5 average rating, 350 reviews, 2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
5.0 out of 5 average rating, 7 reviews, 2 bedrooms, 3 beds, 1.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
4.98 out of 5 average rating, 53 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Oct
Top guest favourite
Flat in Oak Bluffs
111B Beautiful and Short walk beach, town, harbor!
4.93 out of 5 average rating, 87 reviews, 1 bedroom, 2 beds, 1 bathroom
18–23 Aug
Guest house in Oak Bluffs
Charming guesthouse in OB
4.89 out of 5 average rating, 9 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Tisbury
Martha’s Vineyard Waterfront Private Beach
5.0 out of 5 average rating, 18 reviews, 8 bedrooms, 10 beds, 5.5 bathrooms
20–25 Sept
Home in Oak Bluffs
MV Sea Glenn Flower
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
4.98 out of 5 average rating, 86 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
31 Aug – 5 Sept
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
4.83 out of 5 average rating, 66 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
29 Sept – 4 Oct
Top guest favourite
Home in Oak Bluffs
Charming Oak Bluffs Retreat
4.96 out of 5 average rating, 28 reviews, 6 bedrooms, 11 beds, 2.5 bathrooms
27 Sept – 2 Oct