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Search results; Over 1,000 homes in Oak Bluffs

Boutique hotel in Oak Bluffs
MORGAN HOTEL ~ Standard Queen w/ wet bar
1 bedroom, 1 bed, 1 private bathroom
20–25 Sept
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4.88 out of 5 average rating, 17 reviews
Top guest favourite
Guest suite in Oak Bluffs
Lovely 2 BR Oak Bluffs Apartment
2 bedrooms, 2 double beds, 1 bathroom
20–25 Sept
4.95 out of 5 average rating, 434 reviews
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Home in Oak Bluffs
The Blue Lagoon, Oak Bluffs
3 bedrooms, 3 king beds, 3 bathrooms
27 Sept – 2 Oct
4.98 out of 5 average rating, 55 reviews
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Home in Oak Bluffs
Charming Oak Bluffs Retreat
6 bedrooms, 11 beds, 2.5 bathrooms
27 Sept – 2 Oct
4.97 out of 5 average rating, 33 reviews
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Home in Oak Bluffs
The Luxury Vineyard Yurt
2 bedrooms, 3 queen beds, 1 bathroom
25–30 Oct
4.93 out of 5 average rating, 322 reviews
Guest favourite
Home in Oak Bluffs
**Vineyard Vacation Retreat** -3 BR
3 bedrooms, 3 beds, 2 bathrooms
27 Sept – 2 Oct
4.96 out of 5 average rating, 135 reviews
Guest favourite
Cottage in Oak Bluffs
#Islandbeachrose. Walk To Beach and Town!
4 bedrooms, 6 beds, 2 bathrooms
15–20 Sept
4.93 out of 5 average rating, 27 reviews
Top guest favourite
Home in Oak Bluffs
Casa Luca| Serene 3BR| SunRm, Outdr Shwr, A/C, BBQ
3 bedrooms, 5 beds, 1 bathroom
4–9 Oct
4.95 out of 5 average rating, 20 reviews
Guest favourite
Home in Oak Bluffs
New Home Walk to Town & Beaches
4 bedrooms, 4 queen beds, 2.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 11 reviews
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Home in Oak Bluffs
Brand new! MV summer home!
3 bedrooms, 3 beds, 1 bathroom
14–19 Sept
5.0 out of 5 average rating, 12 reviews
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Home in Oak Bluffs
Walk East Chop from Dover House
5 bedrooms, 7 beds, 4.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 36 reviews
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Home in Oak Bluffs
*NEW* 3 min drive to OB Circuit ave
5 bedrooms, 6 beds, 2 bathrooms
20–25 Sept
5.0 out of 5 average rating, 22 reviews
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Home in Oak Bluffs
1/2 mile walk to Downtown Oak Bluffs
3 bedrooms, 7 beds, 2 bathrooms
17–22 Oct
4.97 out of 5 average rating, 36 reviews
Superhost
Home in Oak Bluffs
Oak Bluffs Allure
4 bedrooms, 4 beds, 5 bathrooms
7–12 Sept
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Home in Oak Bluffs
Updated cottage/ ocean views
3 bedrooms, 4 beds, 1.5 bathrooms
27 Sept – 2 Oct
5.0 out of 5 average rating, 27 reviews
Home in Oak Bluffs
OB Retreat Near Lagoon + Town
3 bedrooms, 4 beds, 2 bathrooms
1–6 Jul
New place to stay
Top guest favourite
Cottage in Oak Bluffs
The WestLake
4 bedrooms, 5 beds, 2 bathrooms
24–29 Oct
5.0 out of 5 average rating, 12 reviews
Guest favourite
Home in Oak Bluffs
Sunny 3 bedroom with large deck, porch & kayaks
3 bedrooms, 5 beds, 2 bathrooms
28 May – 4 Jun
5.0 out of 5 average rating, 17 reviews
Guest favourite
Home in Oak Bluffs
Oak Bluffs Victorian Walk to Town & Beaches
5 bedrooms, 7 beds, 5.5 bathrooms
29 Sept – 4 Oct
4.81 out of 5 average rating, 70 reviews