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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, 146 reviews
Place to stay in Oak Bluffs
Oak Bluffs Cottage Walk To Town
1 bedroom, 2 double beds, 1 bathroom
8–15 Aug
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom, 2 beds, 1.5 bathrooms
22–27 Jul
4.95 out of 5 average rating, 189 reviews
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
3 bedrooms, 6 beds, 2.5 bathrooms
29 Sept – 4 Oct
4.98 out of 5 average rating, 83 reviews
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, 309 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds, 2.5 bathrooms
10–15 Oct
4.98 out of 5 average rating, 53 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, 10 reviews
Guest favourite
Home in Oak Bluffs
Brand new! MV summer home!
3 bedrooms, 3 beds, 1 bathroom
19–24 Jul
5.0 out of 5 average rating, 5 reviews
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, 209 reviews
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds, 5.5 bathrooms
29 Sept – 4 Oct
4.83 out of 5 average rating, 65 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
Top guest favourite
Flat in Oak Bluffs
111B Beautiful and Short walk beach, town, harbor!
1 bedroom, 2 beds, 1 bathroom
31 Jul – 5 Aug
4.93 out of 5 average rating, 85 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, 424 reviews
Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds, 3 bathrooms
16–21 Sept
4.98 out of 5 average rating, 51 reviews
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds, 1 bathroom
29 Aug – 3 Sept
4.79 out of 5 average rating, 345 reviews
Superhost
Home in Oak Bluffs
NEW! Charming Oak Bluffs Cottage w/ AC - Sleeps 8
3 bedrooms, 4 beds, 2 bathrooms
18–23 Jul
New place to stay
Guest favourite
Flat in Oak Bluffs
14C Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 22 reviews
Top guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
4.96 out of 5 average rating, 125 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