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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds, 1 private bathroom
29 Aug – 3 Sept
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4.79 out of 5 average rating, 347 reviews
Room in Oak Bluffs
Oak Bluffs Cottage Walk To Town
2 double beds, 1 bathroom
8–15 Aug
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
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
4.95 out of 5 average rating, 192 reviews, 1 bedroom, 2 beds, 1.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Flat in Oak Bluffs
14D Kennebec THE center of OB! No car, No problem!
4.94 out of 5 average rating, 32 reviews, 1 bedroom, 2 beds, 1 bathroom
16–21 Aug
Cabin in Oak Bluffs
Newly built rustic cabin in Oak Bluffs
New place to stay, 1 bedroom, 1 bed, 1 bathroom
30 Aug – 4 Sept
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
Top guest favourite
Home in Tisbury
Martha’s Vineyard Waterfront Private Beach
5.0 out of 5 average rating, 18 reviews, 8 bedrooms, 10 beds, 5.5 bathrooms
20–25 Sept
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
4.95 out of 5 average rating, 213 reviews, 2 bedrooms, 2 beds, 1.5 bathrooms
16–21 Aug
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
Home in Oak Bluffs
Just listed! Bright, cozy, quiet & full of charm
5.0 out of 5 average rating, 4 reviews, 3 bedrooms, 3 beds, 2 bathrooms
20–25 Aug
Top guest favourite
Home in Oak Bluffs
Spectacular beach & pool combo; beautiful sunsets!
4.93 out of 5 average rating, 221 reviews, 4 bedrooms, 5 beds, 5.5 bathrooms
4–9 Oct
Top guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
4.93 out of 5 average rating, 312 reviews, 2 bedrooms, 3 beds, 1 bathroom
16–21 Oct
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
5.0 out of 5 average rating, 3 reviews, 3 bedrooms, 3 beds, 1 bathroom
7–12 Sept
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
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
4.95 out of 5 average rating, 426 reviews, 2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
Featured hotel
Hotel in Oak Bluffs
King
5.0 out of 5 average rating, 6 reviews, 1 bedroom, 1 bed, 1 bathroom
27 Sept – 2 Oct
Guest favourite
Tiny home in Oak Bluffs
Delightful 1BR House near all! Walk to beach.
5.0 out of 5 average rating, 9 reviews, 1 bedroom, 2 beds, 1 bathroom
1–6 Aug
Top guest favourite
Room in Tisbury
Vineyard Haven Sanctuary- free bikes!
4.94 out of 5 average rating, 139 reviews, 1 queen bed, 1 bathroom
13–18 Sept