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Search results; Over 1,000 homes in Oak Bluffs

Top guest favourite

Flat in Oak Bluffs

Absolute Best Location on the Island

2 bedrooms, 4 beds, 1 private bathroom

7–12 Sept

$4,632 SGD for 5 nights

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4.92 out of 5 average rating, 127 reviews

Home in Oak Bluffs

Waterfront Retreat w/ Guest Cottage & Sunsets

4 bedrooms, 5 beds, 2 bathrooms

5–10 Jul

$4,592 SGD for 5 nights

New place to stay

Superhost

Home in Oak Bluffs

Hidden home in the North Bluff

3 bedrooms, 3 beds, 3 bathrooms

1–6 Jul

$11,176 SGD for 5 nights

Free cancellation

5.0 out of 5 average rating, 3 reviews

Guest favourite

Guest suite in Oak Bluffs

Cottage suite between the harbors: no minimum stay

2 bedrooms, 3 beds, 1 bathroom

11–16 Jul

$4,945 SGD for 5 nights

4.79 out of 5 average rating, 341 reviews

Top guest favourite

Home in Oak Bluffs

The Luxury Vineyard Yurt

2 bedrooms, 3 queen beds, 1 bathroom

4–9 Oct

$2,586 SGD for 5 nights

4.92 out of 5 average rating, 305 reviews

Home in Oak Bluffs

Brand new! MV summer home!

3 bedrooms, 3 beds, 1 bathroom

4–9 Jul

$9,194 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Top guest favourite

Home in Oak Bluffs

Charming 3-Bedrm w/Loft.New Construct! Walk 2 town

3 bedrooms, 5 beds, 3.5 bathrooms

6–11 Jul

$7,584 SGD for 5 nights

5.0 out of 5 average rating, 17 reviews

Home in Oak Bluffs

Oak Bluffs Oasis. Walk to town, beach & ferry.

3 bedrooms, 3 beds, 1 bathroom

6–11 Jul

$4,381 SGD for 5 nights

New place to stay

Home in Oak Bluffs

East Chop Oceanview Escape

6 bedrooms, 8 beds, 4.5 bathrooms

4–10 Jul

$25,445 SGD for 6 nights

5.0 out of 5 average rating, 4 reviews

Superhost

Home in Oak Bluffs

Half a Mile to Downtown Oak Bluffs!

3 bedrooms, 3 beds, 2 bathrooms

8–13 Jul

$5,562 SGD for 5 nights

Guest favourite

Home in Oak Bluffs

Sunny new 3-bed just minutes to beach and town

3 bedrooms, 3 beds, 2 bathrooms

31 Jul – 5 Aug

$4,305 SGD for 5 nights

Free cancellation

4.89 out of 5 average rating, 28 reviews

Home in Oak Bluffs

New Serenity Retreat

2 bedrooms, 3 beds, 1.5 bathrooms

6–11 Jul

$6,019 SGD for 5 nights

5.0 out of 5 average rating, 4 reviews

Top guest favourite

Cottage in Oak Bluffs

Beautiful and walk to everything Oak Bluffs!

1 bedroom, 2 beds, 1.5 bathrooms

22–27 Jul

4.97 out of 5 average rating, 176 reviews

Guest favourite

Home in Oak Bluffs

Walk to Town, beach and amazing location 113A

2 bedrooms, 2 beds, 1.5 bathrooms

5–10 Jul

4.95 out of 5 average rating, 205 reviews

Guest favourite

Flat in Tisbury

Martha's Vineyard Pied-á-terre #2 Vineyard Haven

1 bedroom, 1 queen bed, 1 bathroom

5–10 Jul

$3,109 SGD for 5 nights

4.88 out of 5 average rating, 168 reviews

Superhost

Home in Oak Bluffs

Martha’s Vineyard Boutique Beach Cottage!

3 bedrooms, 6 beds, 2 bathrooms

14–19 Sept

$5,650 SGD for 5 nights

5.0 out of 5 average rating, 3 reviews

Guest favourite

Cottage in Oak Bluffs

Beautiful clean walk to Town, Inkwell and harbor!

1 bedroom, 2 beds, 1.5 bathrooms

9–14 Jul

4.95 out of 5 average rating, 185 reviews

Guest favourite

Home in Oak Bluffs

Peaceful, spacious island escape near Alpaca Farm

3 bedrooms, 9 beds, 2.5 bathrooms

5–12 Jul

5.0 out of 5 average rating, 43 reviews

Top guest favourite

Home in Oak Bluffs

Pinkletink Plantation

3 bedrooms, 5 beds, 2.5 bathrooms

10–15 Oct

$3,810 SGD for 5 nights

Free cancellation

4.98 out of 5 average rating, 47 reviews