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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 beds, 1 private bathroom
16–21 Oct
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4.93 out of 5 average rating, 311 reviews
Top guest favourite
Cottage in Oak Bluffs
The WestLake
5.0 out of 5 average rating, 10 reviews, 4 bedrooms, 5 beds, 2 bathrooms
3–8 Oct
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
10–15 Oct
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
4.95 out of 5 average rating, 191 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
30 Jul – 4 Aug
Guest favourite
Home in Oak Bluffs
New Pristine Luxury Home on Martha's Vineyard
4.98 out of 5 average rating, 83 reviews, 3 bedrooms, 6 beds, 2.5 bathrooms
29 Sept – 4 Oct
Home in Oak Bluffs
MV Sea Glenn Flower
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
4.95 out of 5 average rating, 212 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
Guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 424 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
4.93 out of 5 average rating, 15 reviews, 3 bedrooms, 5 beds, 1 bathroom
2–7 Aug
Room in Oak Bluffs
Oak Bluffs Cottage Walk To Town
2 double beds, 1 bathroom
8–15 Aug
Top guest favourite
Home in Oak Bluffs
** Vineyard Vacation Retreat ** with HOT TUB
4.92 out of 5 average rating, 146 reviews, 2 bedrooms, 2 beds, 2.5 bathrooms
19–24 Sept
Top guest favourite
Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
4.98 out of 5 average rating, 52 reviews, 3 bedrooms, 3 beds, 3 bathrooms
27 Sept – 2 Oct
Top guest favourite
Flat in Oak Bluffs
111C Beautiful private condo walk to everything!
4.95 out of 5 average rating, 195 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Guest favourite
Home in Oak Bluffs
Modern cabin in the woods.
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Aug
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
4.83 out of 5 average rating, 65 reviews, 5 bedrooms, 7 beds, 5.5 bathrooms
29 Sept – 4 Oct
Guest favourite
Home in Oak Bluffs
Brand new! MV summer home!
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 3 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
4.96 out of 5 average rating, 126 reviews, 3 bedrooms, 3 beds, 2 bathrooms
8–13 Sept
Guest favourite
Home in Oak Bluffs
Renovated Downtown Charmer, 3 Blocks to the Beach
5.0 out of 5 average rating, 5 reviews, 3 bedrooms, 7 beds, 2 bathrooms
27 Sept – 2 Oct
Top guest favourite
Home in Tisbury
Sunny, Spacious Vineyard Retreat
4.97 out of 5 average rating, 302 reviews, 3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept