The 10 best holiday homes in Oak Bluffs, USA | Booking.com
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Holiday Homes in Oak Bluffs

Find the holiday homes that appeal to you the most

The best holiday homes in Oak Bluffs

Check out our pick of great holiday homes in Oak Bluffs

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Fresh Pond Chateau Renovated Bright and Cozy Home

Oak Bluffs

Set in Oak Bluffs, 8.2 km from Edgartown Lighthouse, Fresh Pond Chateau Renovated Bright and Cozy Home offers air-conditioned accommodation with a balcony and free WiFi.

s
steven
From
United Kingdom
Very luxurious house, extremely well equipped, quiet and private
Scored out of 10, guest rating 9.1
Superb - What previous guests thought, 6 reviews
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Winthrop Cottage

Oak Bluffs

Featuring accommodation with a patio, Winthrop Cottage is located in Oak Bluffs. Located around 1.1 km from Oak Bluffs Town Beach, the holiday home is also 10 km away from Edgartown Lighthouse.

Scored out of 10, guest rating 8.0
Very good - What previous guests thought, 6 reviews
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Canary Cottage

Oak Bluffs

Set in Oak Bluffs in the Massachusetts region, Canary Cottage has a terrace. Guests staying at this holiday home have access to a balcony. The holiday home features facilities for disabled guests.

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 7 reviews
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Yellow Brick Road House

Oak Bluffs

Located in Oak Bluffs, less than 1 km from Eastville Beach and 12 km from Edgartown Lighthouse, Yellow Brick Road House offers air conditioning.

A
Ani
From
Bulgaria
It was a great house with a huge yard. The property was very specious and comfortable for three people. Very good wi-fi.
Scored out of 10, guest rating 7.3
Good - What previous guests thought, 13 reviews
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Oak Bluffs Cottage

Oak Bluffs

Boasting air-conditioned accommodation with a terrace, Oak Bluffs Cottage is situated in Oak Bluffs. This holiday home features accommodation with a balcony.

K
Kevin
From
United Kingdom
Lovely looking 3 bedroom house in a great location - 10 minutes walk into Oak Bluffs.
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 8 reviews
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Sea Glen Cottage

Oak Bluffs

Sea Glen Cottage offers accommodation in Oak Bluffs, 10 km from Edgartown Lighthouse. Guests can benefit from a patio and a children's playground.

Scored out of 10, guest rating 5.8
Passable - What previous guests thought, 6 reviews
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Vineyard Charm

Edgartown (Near Oak Bluffs)

Set 1.8 km from Lighthouse Beach, Vineyard Charm offers accommodation with a patio. There is a private entrance at the holiday home for the convenience of those who stay.

Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 5 reviews
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Wooded Oasis

Edgartown (Near Oak Bluffs)

Situated 6.6 km from Edgartown Lighthouse, Wooded Oasis features accommodation in Edgartown. The property features a restaurant with an outdoor dining area.

Scored out of 10, guest rating 7.8
Good - What previous guests thought, 5 reviews
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Sunset on the Vineyard

Vineyard Haven (Near Oak Bluffs)

Set in Vineyard Haven, 2.3 km from Tisbury Town Beach and 16 km from Edgartown Lighthouse, Sunset on the Vineyard offers a restaurant and sea views. The property has garden views.

Scored out of 10, guest rating 5.6
Passable - What previous guests thought, 6 reviews
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The CAVU Mansion on Bellevue

Oklahoma Heights (Near Oak Bluffs)

Set in Oklahoma Heights in the Massachusetts region, The CAVU Mansion on Bellevue features a patio.

Scored out of 10, guest rating 7.1
Good - What previous guests thought, 7 reviews
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All holiday homes in Oak Bluffs

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes in Oak Bluffs and surroundings in the past month

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Great access to the city centre. Check these holiday homes in Oak Bluffs and nearby

  • Situated in Oak Bluffs in the Massachusetts region, Bird Street Breeze features a patio. Guests can benefit from a balcony and an outdoor fireplace.

  • Vineyard Haven

    Oak Bluffs
    Central location
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    Situated 1.6 km from Oak Bluffs Town Beach and 11 km from Edgartown Lighthouse, Vineyard Haven features accommodation located in Oak Bluffs. Guests can benefit from a patio and a picnic area.

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 8 reviews

    Boasting air-conditioned accommodation with a terrace, Oak Bluffs Cottage is situated in Oak Bluffs. This holiday home features accommodation with a balcony.

  • Located in Oak Bluffs, Birds of Paradise features accommodation 11 km from Edgartown Lighthouse. The property is non-smoking and is situated 1.1 km from Oak Bluffs Town Beach.

  • Scored out of 10, guest rating 6.0
    Pleasant - What previous guests thought, 4 reviews

    Set in Oak Bluffs, Oak Leaf Cape Cottage features accommodation within 11 km of Edgartown Lighthouse. Guests can benefit from a patio and a children's playground.

  • Boasting air-conditioned accommodation with a patio, The Rootskeller is situated in Oak Bluffs. The holiday home is 1.5 km from Eastville Beach.

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

    Set in Oak Bluffs in the Massachusetts region, Gingerbread Dream features a balcony. Guests can benefit from a terrace and a children's playground.

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

    Set in Oak Bluffs in the Massachusetts region, Charming MV Cottage Walk to Dtwn Oak Bluffs! features a balcony. It is located 1.2 km from Oak Bluffs Town Beach and offers a 24-hour front desk.

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

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    11 km from Edgartown Lighthouse in Vineyard Haven, Marthas Vineyard Home Walk to Oak Bluffs Beach! provides accommodation with access to a spa centre.

  • Canary Cottage

    Oak Bluffs
    Budget options available
    Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 7 reviews

    Set in Oak Bluffs in the Massachusetts region, Canary Cottage has a terrace. Guests staying at this holiday home have access to a balcony. The holiday home features facilities for disabled guests.

  • Sunny Side Up

    Oak Bluffs
    Budget options available

    Located in Oak Bluffs, 2 km from Eastville Beach and 12 km from Edgartown Lighthouse, Sunny Side Up provides a restaurant. Guests staying at this holiday home have access to a patio.

  • Oak Bluffs Beauty

    Oak Bluffs
    Budget options available
    Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 3 reviews

    Boasting air-conditioned accommodation with a patio, Oak Bluffs Beauty is set in Oak Bluffs. This holiday home is 1.2 km from Eastville Beach and 12 km from Edgartown Lighthouse.

  • Island Getaway

    Oak Bluffs
    Budget options available
    Scored out of 10, guest rating 3.5
    Poor - What previous guests thought, 7 reviews

    Offering garden views, Island Getaway is an accommodation set in Oak Bluffs, 1.2 km from Eastville Beach and 12 km from Edgartown Lighthouse. The property has a restaurant with an outdoor dining area.

  • Sunset Meadows

    Oak Bluffs
    Budget options available

    Offering lake views, Sunset Meadows is an accommodation situated in Oak Bluffs, 1.1 km from Eastville Beach and 12 km from Edgartown Lighthouse.

  • Brewster House

    Oak Bluffs
    Budget options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    Brewster House enjoys a location in Oak Bluffs, just 1.4 km from Eastville Beach and 11 km from Edgartown Lighthouse. Guests can benefit from a patio and a children's playground.

  • Sankofa Martha's Vineyard

    Oak Bluffs
    Budget options available

    Located in Oak Bluffs, less than 1 km from Oak Bluffs Town Beach and 11 km from Edgartown Lighthouse, Sankofa Martha's Vineyard offers air conditioning.

Enjoy breakfast in Oak Bluffs and nearby

  • Sankofa House

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

    Boasting air-conditioned accommodation with a patio, Sankofa House is set in Oak Bluffs.

  • Scored out of 10, guest rating 7.2
    Good - What previous guests thought, 13 reviews

    Located in Oak Bluffs, less than 1 km from Eastville Beach and 12 km from Edgartown Lighthouse, Yellow Brick Road House offers air conditioning.

  • Located 800 metres from Inkwell Beach and 10 km from Edgartown Lighthouse, Blissful Island Haven provides accommodation in Oak Bluffs. Guests can benefit from a patio and a children's playground.

  • The Pinkletink

    Oak Bluffs
    Breakfast options
    Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 1 review

    Offering garden views, The Pinkletink is an accommodation located in Oak Bluffs, 800 metres from Inkwell Beach and 10 km from Edgartown Lighthouse.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 3 reviews

    Boasting accommodation with a terrace, Victorian by the Sea is situated in Oak Bluffs. Guests staying at this holiday home have access to a balcony.

  • Island Dream

    Oak Bluffs
    Breakfast options

    Located in Oak Bluffs, 200 metres from Oak Bluffs Town Beach and 10 km from Edgartown Lighthouse, Island Dream offers air conditioning. The property features a restaurant with an outdoor dining area.

  • Situated in Vineyard Haven, 200 metres from Oak Bluffs Town Beach and 10 km from Edgartown Lighthouse, Steps to Inkwell Beach Victorian Home!

  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 3 reviews

    Boasting garden views, Home in Oak Bluffs features accommodation with a garden and a patio, around 3 km from Eastville Beach.

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