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Search results; Over 1,000 homes in Oak Bluffs

Guest favourite
Home in Oak Bluffs
Waterview, Private, Walk to Beach, Mile to Town
2 bedrooms, 4 beds, 1.5 private bathrooms
14–19 Sept
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4.83 out of 5 average rating, 215 reviews
Home in Tisbury
Vineyard Haven Hideaway
3 bedrooms, 4 beds, 2.5 bathrooms
1–8 Aug
New place to stay
Home in Oak Bluffs
MV Sea Glenn Flower
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
5.0 out of 5 average rating, 3 reviews
Home in Tisbury
Island getaway, Minutes from Lake Tashmoo.
4 bedrooms, 7 beds, 3 bathrooms
24–29 Aug
New place to stay
Room in Oak Bluffs
Oak Bluffs Cottage Walk To Town
2 double beds, 1 bathroom
8–15 Aug
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
Cottage in Oak Bluffs
111G Beautiful walk to Town, Inkwell and harbor!
1 bedroom, 2 beds, 1.5 bathrooms
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, 1.5 bathrooms
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, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Flat in Oak Bluffs
14D Kennebec THE center of OB! No car, No problem!
1 bedroom, 2 beds, 1 bathroom
16–21 Aug
4.94 out of 5 average rating, 32 reviews
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds, 1 bathroom
2–7 Aug
4.93 out of 5 average rating, 15 reviews
Top 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, 213 reviews
Guest favourite
Home in Oak Bluffs
Modern cabin in the woods.
3 bedrooms, 4 beds, 1.5 bathrooms
1–6 Aug
5.0 out of 5 average rating, 7 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
Home in Oak Bluffs
Oak Bluffs Oasis. Walk to town, beach & ferry.
3 bedrooms, 3 beds, 1 bathroom
22–28 Aug
5.0 out of 5 average rating, 3 reviews
Home in Oak Bluffs
OB Salt & Cedar Cottage
4 bedrooms, 9 beds, 2 bathrooms
24–31 Aug
5.0 out of 5 average rating, 3 reviews
Apartment in Oak Bluffs
Heart of Oak Bluffs, Walk to Beach & Ferries
2 bedrooms, 4 beds, 1 bathroom
1–6 Aug
New place to stay
Home in Oak Bluffs
Charming 3BR Cottage Near the Beach w/ Deck
3 bedrooms, 4 beds, 1 bathroom
30 Aug – 4 Sept
Top guest favourite
Home in Tisbury
Sunny, Spacious Vineyard Retreat
3 bedrooms, 5 beds, 2.5 bathrooms
20–25 Sept
4.97 out of 5 average rating, 302 reviews