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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 beds, 1 bathroom
18–23 Oct
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4.95 out of 5 average rating, 426 reviews
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds
3–8 Oct
5.0 out of 5 average rating, 10 reviews
Guest favourite
Flat in Oak Bluffs
14C Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds
18–23 Aug
5.0 out of 5 average rating, 24 reviews
Guest favourite
Cottage in Oak Bluffs
111G Beautiful walk to Town, Inkwell and harbor!
1 bedroom, 2 beds
24–29 Aug
4.94 out of 5 average rating, 222 reviews
Guest favourite
Cottage in Oak Bluffs
111H Beautiful clean walk to Town, Inkwell, harbor
1 bedroom, 2 beds
30 Aug – 4 Sept
4.95 out of 5 average rating, 192 reviews
Guest favourite
Home in Oak Bluffs
New Serenity Retreat
2 bedrooms, 3 beds
1–6 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in Oak Bluffs
113A Walk to Town, beach and amazing location!
2 bedrooms, 2 beds
16–21 Aug
4.95 out of 5 average rating, 213 reviews
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds
2–7 Aug
4.93 out of 5 average rating, 15 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
OB Salt & Cedar Cottage
4 bedrooms, 9 beds
24–31 Aug
5.0 out of 5 average rating, 3 reviews
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
3 bedrooms, 3 beds
22–28 Aug
5.0 out of 5 average rating, 3 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
Guest favourite
Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds
16–21 Oct
4.93 out of 5 average rating, 312 reviews
Guest favourite
Home in Oak Bluffs
Modern cabin in the woods.
3 bedrooms, 4 beds
1–6 Aug
5.0 out of 5 average rating, 7 reviews
Guest favourite
Guest suite in Oak Bluffs
Cottage suite between the harbors: no minimum stay
2 bedrooms, 3 beds
29 Aug – 3 Sept
4.79 out of 5 average rating, 347 reviews
Flat in Oak Bluffs
Island Oasis
1 bedroom, 3 beds
2–7 Aug
5.0 out of 5 average rating, 4 reviews
Home in Oak Bluffs
Oak Bluffs retreat with direct pond access
4 bedrooms, 6 beds
28 Sept – 3 Oct
5.0 out of 5 average rating, 4 reviews
Guest favourite
Home in Tisbury
Luxurious New Construction in Vineyard Haven
4 bedrooms, 1 queen bed
29 Aug – 3 Sept
5.0 out of 5 average rating, 6 reviews