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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Cottage in Oak Bluffs
East Chop Cottage - walk to lighthouse & beach!
1 bedroom, 1 bed, 0.5 private bathroom
20–25 Sept
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4.9 out of 5 average rating, 149 reviews
Top guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4 bedrooms, 5 beds
4–9 Oct
4.93 out of 5 average rating, 221 reviews
Home in Oak Bluffs
East Chop Oceanview Escape
6 bedrooms, 8 beds
21–27 Aug
5.0 out of 5 average rating, 5 reviews
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, 431 reviews
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
3 bedrooms, 6 beds
31 Aug – 5 Sept
4.98 out of 5 average rating, 86 reviews
Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds
27 Sept – 2 Oct
4.98 out of 5 average rating, 54 reviews
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds
19–24 Oct
4.93 out of 5 average rating, 316 reviews
Top guest favourite
Home in Tisbury
Martha’s Vineyard Waterfront Private Beach
8 bedrooms, 10 beds
20–25 Sept
5.0 out of 5 average rating, 18 reviews
Home in Oak Bluffs
Amanda’s Veranda
4 bedrooms, 5 beds
27 Sept – 2 Oct
New place to stay
Top guest favourite
Guest suite in Oak Bluffs
Quiet Hide Away
1 bedroom, 1 queen bed
20–25 Aug
4.98 out of 5 average rating, 202 reviews
Guest favourite
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds
3–8 Oct
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds
8–13 Sept
4.96 out of 5 average rating, 131 reviews
Top guest favourite
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
1 bedroom, 1 bed
13–18 Sept
5.0 out of 5 average rating, 10 reviews
Superhost
Home in Oak Bluffs
Oak Bluffs 4BR • 5 Min Drive to Downtown
4 bedrooms, 4 beds
27 Sept – 2 Oct
4.88 out of 5 average rating, 68 reviews
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms, 3 beds
29 Aug – 3 Sept
5.0 out of 5 average rating, 7 reviews
Top guest favourite
Home in Oak Bluffs
*NEW* 3 min drive to OB Circuit ave
5 bedrooms, 6 beds
30 Aug – 4 Sept
5.0 out of 5 average rating, 22 reviews
Guest favourite
Home in Oak Bluffs
Brand new! MV summer home!
3 bedrooms, 3 beds
26–31 Aug
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Oak Bluffs
Pinkletink Plantation
3 bedrooms, 5 beds
16–21 Oct
4.98 out of 5 average rating, 58 reviews