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Vacation Homes in Oak Bluffs

Find the vacation homes that appeal to you the most

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The best vacation homes in Oak Bluffs

Check out our selection of great vacation homes in Oak Bluffs

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< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs

Oak Bluffs

< 1 Mi to Beaches: Home w/ Deck in Oak Bluffs is located in Oak Bluffs, just a 15-minute walk from Oak Bluffs Town Beach and 6.9 miles from Edgartown Lighthouse.

R
Robin
From
United States
Very convenient location and clean.
Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 7 reviews
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Canary Cottage

Oak Bluffs

Canary Cottage offers accommodations in Oak Bluffs, a 13-minute walk from Oak Bluffs Town Beach and 6.8 miles from Edgartown Lighthouse.

m
marian
From
United States
The property was clean and mainly comfortable. It is not in the bustling part of Oak Bluffs, but an easy walk into the town. It is exceptionally quiet, ensuring a good night’s rest.
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 5 reviews
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Yellow Brick Road House

Oak Bluffs

Yellow Brick Road House offers accommodations in Oak Bluffs, a 10-minute walk from Eastville Beach and 7.5 miles from Edgartown Lighthouse. Outdoor seating is also available at the vacation home.

L
Larry
From
United States
3 bedroom ranch style home. Accessible for me and my wife as we are both in our 70’s.
Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 12 reviews
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Oak Bluffs Cottage

Oak Bluffs

Oak Bluffs Cottage is located in Oak Bluffs, just a 12-minute walk from Oak Bluffs Town Beach and 6.8 miles from Edgartown Lighthouse.

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 6 reviews
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Sea Glen Cottage

Oak Bluffs

Sea Glen Cottage offers accommodations in Oak Bluffs, 6.4 miles from Edgartown Lighthouse. This vacation home offers a garden. Outdoor seating is also available at the vacation home.

N
Nicole
From
United States
Location was good and very clean
Scored out of 10, guest rating 6.8
Pleasant - What previous guests thought, 6 reviews
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Island Sanctuary

Oak Bluffs

Island Sanctuary is located in Oak Bluffs, just 6.8 miles from Edgartown Lighthouse and 3.1 miles from Martha'S Vineyard Hist'L Island Trs.

K
K.
From
United States
All went well & thank you. Enjoyed the property & surroundings.
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 9 reviews
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Family-Friendly Tisbury Escape - Walk to Town

Vineyard Haven (Near Oak Bluffs)

Family-Friendly Tisbury Escape - Walk to Town is located in Vineyard Haven, just 1.3 miles from Owen Park Beach and 1.1 miles from Louisa Gould Gallery.

W
Walton Masters
From
United States
Clean, organized, comfortable!
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 7 reviews
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The CAVU Mansion on Bellevue

Oklahoma Heights (Near Oak Bluffs)

The CAVU Mansion on Bellevue is located in Oklahoma Heights, just 1.4 miles from Owen Park Beach and 7.2 miles from Edgartown Lighthouse.

N
Nnenna
From
United States
Loved the spacious rooms and bathrooms . Great for a group trip of 8 girls.
Scored out of 10, guest rating 7.0
Good - What previous guests thought, 6 reviews
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Chilmark Guest House

Chilmark (Near Oak Bluffs)

Featuring a garden, Chilmark Guest House features accommodations in Chilmark. The air-conditioned accommodation is 15 miles from Edgartown Lighthouse.

J
Jeff
From
United States
Everything was great. Perfectly fit what we had in mind for a short stay on Martha's Vineyard. Was easy enough to locate using gps maps, made a few little goofs navigating the driveway through the woods that go to other properties, but no big deal. It was neatly hidden away in the quiet woods, complete with the occasional cute woodland creatures. It was clean and the layout is really neat. The kitchen was very useful and complete. The washing machine got the job done fine. The bathroom's a little small, but worked good. The shower water pressure is much stronger than I'd expected it would on the island. And the provided detergents/soaps were handy. It's interesting how few bugs there are in the area, as very few would gather around the porch light compared to places we're used to. And the night sky's very clear. Anyway, just a great spot we hope we could return to some day, if we're lucky. Thanks!
Scored out of 10, guest rating 8.6
Excellent - What previous guests thought, 6 reviews
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Pretty on Prada

Edgartown (Near Oak Bluffs)

Pretty on Prada offers accommodations in Edgartown, 1.8 miles from South Beach and 2.2 miles from Edgartown Lighthouse. This vacation home provides a garden.

Y
Yelman
From
United States
Great place. Very clean. Was nicely prepared for our arrival. Very home like feeding. Everything is great.
Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 6 reviews
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All vacation homes in Oak Bluffs

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Oak Bluffs and surrounding area in the past month

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Popular with guests booking vacation homes in Oak Bluffs

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Popular with guests booking vacation homes in Oak Bluffs

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 3 reviews

Popular with guests booking vacation homes in Oak Bluffs

Popular with guests booking vacation homes in Oak Bluffs

Scored out of 10, guest rating 6.8
Pleasant - What previous guests thought, 6 reviews

Popular with guests booking vacation homes in Oak Bluffs

Popular with guests booking vacation homes in Oak Bluffs

Popular with guests booking vacation homes in Oak Bluffs

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 6 reviews

Popular with guests booking vacation homes in Oak Bluffs

Scored out of 10, guest rating 8.1
Very Good - What previous guests thought, 7 reviews

Popular with guests booking vacation homes in Oak Bluffs

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

Popular with guests booking vacation homes in Oak Bluffs

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 3 reviews

Great access to the city center. Check these vacation homes in Oak Bluffs and nearby

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Bird Street Breeze is located in Oak Bluffs, just a 18-minute walk from Oak Bluffs Town Beach and 7.1 miles from Edgartown Lighthouse.

Scored out of 10, guest rating 7.6
Good - What previous guests thought, 6 reviews

Oak Bluffs Cottage is located in Oak Bluffs, just a 12-minute walk from Oak Bluffs Town Beach and 6.8 miles from Edgartown Lighthouse.

Scored out of 10, guest rating 6.3
Pleasant - What previous guests thought, 3 reviews

Oak Leaf Cape Cottage is located in Oak Bluffs, just a 14-minute walk from Oak Bluffs Town Beach and 6.9 miles from Edgartown Lighthouse.

A 17-minute walk from Eastville Beach in Oak Bluffs, The Rootskeller features accommodations with access to a spa center. Guests staying at this vacation home have access to a patio.

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 3 reviews

Gingerbread Dream is located in Oak Bluffs, just a 13-minute walk from Oak Bluffs Town Beach and 6.8 miles from Edgartown Lighthouse. This vacation home offers a garden.

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 3 reviews

Winthrop Cottage is located in Oak Bluffs, just a 13-minute walk from Oak Bluffs Town Beach and 6.4 miles from Edgartown Lighthouse.

Canary Cottage

Oak Bluffs
Central location
Scored out of 10, guest rating 7.8
Good - What previous guests thought, 5 reviews

Canary Cottage offers accommodations in Oak Bluffs, a 13-minute walk from Oak Bluffs Town Beach and 6.8 miles from Edgartown Lighthouse.

Sunny Side Up

Oak Bluffs
Central location

Sunny Side Up offers accommodations in Oak Bluffs, 1.2 miles from Eastville Beach and 7.2 miles from Edgartown Lighthouse. This vacation home provides air-conditioned accommodations with a balcony.

Enjoy breakfast in Oak Bluffs and nearby

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Island Getaway

Oak Bluffs
Breakfast options
Scored out of 10, guest rating 3.4
Poor - What previous guests thought, 5 reviews

Island Getaway is located in Oak Bluffs, just a 14-minute walk from Eastville Beach and 7.7 miles from Edgartown Lighthouse. Outdoor seating is also available at the vacation home.

Scored out of 10, guest rating 4.5
Disappointing - What previous guests thought, 2 reviews

Oak Bluffs Beauty is located in Oak Bluffs, just a 14-minute walk from Eastville Beach and 7.2 miles from Edgartown Lighthouse. Guests staying at this vacation home have access to a patio.

Brewster House

Oak Bluffs
Breakfast options
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Brewster House is located in Oak Bluffs, just a 16-minute walk from Eastville Beach and 7 miles from Edgartown Lighthouse. Guests staying at this vacation home have access to a patio.

Sankofa Martha's Vineyard offers accommodations in Oak Bluffs, a 11-minute walk from Oak Bluffs Town Beach and 6.7 miles from Edgartown Lighthouse. This vacation home provides a garden.

Sankofa House

Oak Bluffs
Breakfast options
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Sankofa House offers accommodations in Oak Bluffs, a 11-minute walk from Oak Bluffs Town Beach and 6.7 miles from Edgartown Lighthouse.

Scored out of 10, guest rating 6.6
Pleasant - What previous guests thought, 12 reviews

Yellow Brick Road House offers accommodations in Oak Bluffs, a 10-minute walk from Eastville Beach and 7.5 miles from Edgartown Lighthouse. Outdoor seating is also available at the vacation home.

Sunset Meadows

Oak Bluffs
Breakfast options

Sunset Meadows offers accommodations in Oak Bluffs, 7.5 miles from Edgartown Lighthouse. The air-conditioned accommodation is a 11-minute walk from Eastville Beach.

Blissful Island Haven is located in Oak Bluffs, just a 9-minute walk from Inkwell Beach and 6 miles from Edgartown Lighthouse. This vacation home provides air-conditioned accommodations with a patio.

Save money on vacation homes in Oak Bluffs and nearby – budget options available

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The Pinkletink

Oak Bluffs
Budget options available

The Pinkletink is located in Oak Bluffs, just a 9-minute walk from Inkwell Beach and 6 miles from Edgartown Lighthouse. This vacation home provides a garden.

Victorian by the Sea

Oak Bluffs
Budget options available
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 3 reviews

Victorian by the Sea offers accommodations in Oak Bluffs, 6.2 miles from Edgartown Lighthouse. The air-conditioned accommodation is a 3-minute walk from Oak Bluffs Town Beach.

Island Dream

Oak Bluffs
Budget options available

Island Dream offers accommodations in Oak Bluffs, 6.1 miles from Edgartown Lighthouse. The air-conditioned accommodation is a 2-minute walk from Oak Bluffs Town Beach.

Steps to Inkwell Beach: Victorian Home! offers accommodations in Vineyard Haven, 6.1 miles from Edgartown Lighthouse. This vacation home features accommodations with a balcony.

Island Sanctuary

Oak Bluffs
Budget options available
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 9 reviews

Island Sanctuary is located in Oak Bluffs, just 6.8 miles from Edgartown Lighthouse and 3.1 miles from Martha'S Vineyard Hist'L Island Trs.

Set Sail

Oak Bluffs
Budget options available
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 4 reviews

Featuring a garden, Set Sail features accommodations in Oak Bluffs. The air-conditioned accommodation is 6.7 miles from Edgartown Lighthouse. Outdoor seating is also available at the vacation home.

Twin Ponds

Oak Bluffs
Budget options available

Twin Ponds offers accommodations in Oak Bluffs, 6 miles from Edgartown Lighthouse. Guests staying at this vacation home have access to a patio. Outdoor seating is also available at the vacation home.

Soundmeadow House

Oak Bluffs
Budget options available

Providing a garden, Soundmeadow House provides accommodations in Oak Bluffs. The air-conditioned accommodation is 5.8 miles from Edgartown Lighthouse.