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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds, 1 private bathroom
30 Aug – 4 Sept
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4.8 out of 5 average rating, 351 reviews
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds, 3.5 bathrooms
30 Aug – 4 Sept
New place to stay
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bathroom
19–24 Oct
4.93 out of 5 average rating, 314 reviews
Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds, 2 bathrooms
3–8 Oct
5.0 out of 5 average rating, 12 reviews
Home in Oak Bluffs
Newly restored cottage in downtown Oak Bluffs!
3 bedrooms, 7 beds, 1 bathroom
13–18 Sept
New place to stay
Home in Oak Bluffs
Oak Bluffs Summer Home
3 bedrooms, 4 beds, 2 bathrooms
5–10 Sept
New place to stay
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, 427 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds, 2.5 bathrooms
16–21 Oct
4.98 out of 5 average rating, 54 reviews
Superhost
Home in Oak Bluffs
Cozy, Central Island Family Home
5 bedrooms, 7 beds, 2 bathrooms
26 Jul – 1 Aug
5.0 out of 5 average rating, 3 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, 34 reviews
Top guest favourite
Home in Oak Bluffs
*NEW* 3 min drive to OB Circuit ave
5 bedrooms, 6 beds, 2 bathrooms
30 Aug – 4 Sept
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Cottage in Oak Bluffs
111I Beautiful and walk to everything Oak Bluffs!
1 bedroom, 2 beds, 1.5 bathrooms
13–18 Sept
4.97 out of 5 average rating, 183 reviews
Home in Oak Bluffs
East Chop Oceanview Escape
6 bedrooms, 8 beds, 4.5 bathrooms
21–27 Aug
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
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
5.0 out of 5 average rating, 3 reviews
Guest house in Oak Bluffs
Charming guesthouse in OB
1 bedroom, 2 beds, 1 bathroom
23–28 Aug
4.89 out of 5 average rating, 9 reviews
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
3 bedrooms, 6 beds, 2.5 bathrooms
31 Aug – 5 Sept
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Home in Oak Bluffs
** Vineyard Vacation Retreat ** with HOT TUB
2 bedrooms, 2 beds, 2.5 bathrooms
19–24 Sept
4.92 out of 5 average rating, 146 reviews
Home in Oak Bluffs
Waterfront Retreat w/ Guest Cottage & Sunsets
4 bedrooms, 5 beds, 2 bathrooms
11–16 Sept
New place to stay