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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
impeccable cottage STEPS to downtown OB & beach!
3 bedrooms, 6 beds, 1 private bathroom
20–25 Sept
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4.92 out of 5 average rating, 210 reviews
Home in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 double beds, 1 bathroom
8–15 Aug
Superhost
Flat in Falmouth
On the Shores of Eel Pond
2 bedrooms, 2 queen beds, 2 bathrooms
22–27 Aug
New place to stay
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds, 3.5 bathrooms
22–27 Aug
New place to stay
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
4.95 out of 5 average rating, 213 reviews
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4 bedrooms, 5 beds, 5.5 bathrooms
4–9 Oct
4.93 out of 5 average rating, 221 reviews
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bathroom
16–21 Oct
4.93 out of 5 average rating, 313 reviews
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
4.8 out of 5 average rating, 349 reviews
Guest house in Oak Bluffs
Charming guesthouse in OB
1 bedroom, 2 beds, 1 bathroom
1–6 Aug
4.88 out of 5 average rating, 8 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds, 1 bathroom
18–23 Oct
4.95 out of 5 average rating, 426 reviews
Top guest favourite
Home in Tisbury
Martha’s Vineyard Waterfront Private Beach
8 bedrooms, 10 beds, 5.5 bathrooms
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Top guest favourite
Flat in Oak Bluffs
14D Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Flat in Oak Bluffs
111B Beautiful and Short walk beach, town, harbor!
1 bedroom, 2 beds, 1 bathroom
18–23 Aug
4.93 out of 5 average rating, 87 reviews
Featured hotel
Room in Oak Bluffs
Water view double queen
2 queen beds, 1 bathroom
16–21 Sept
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Home in Tisbury
Sunny, Spacious Vineyard Retreat
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 302 reviews
Flat in Oak Bluffs
Island Oasis
1 bedroom, 3 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 6 reviews
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom, 2 beds, 1.5 bathrooms
13–18 Sept
4.95 out of 5 average rating, 193 reviews