The 10 best holiday rentals in Oak Bluffs, USA | Booking.com
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Holiday Rentals in Oak Bluffs

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The best holiday rentals in Oak Bluffs

Check out our pick of great holiday rentals in Oak Bluffs

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

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These holiday rentals in Oak Bluffs and nearby have options with free cancellation

  • Vineyard Haven

    Oak Bluffs
    Free cancellation options available
    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.

  • Oak Bluffs Cottage

    Oak Bluffs
    Free cancellation options available
    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.

  • Oak Leaf Cape Cottage

    Oak Bluffs
    Free cancellation options available
    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.

  • 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.

  • Sunny Side Up

    Oak Bluffs
    Free cancellation 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
    Free cancellation 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
    Free cancellation 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
    Free cancellation 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.

Highly rated holiday rentals in Oak Bluffs and nearby

  • Scored out of 10, guest rating 9.9
    Exceptional - What previous guests thought, 67 reviews

    Featuring an outdoor pool and complimentary bicycles for guest use, this Vineyard Haven inn is just 15 minutes’ walk from the Vineyard Haven ferry terminal. Free Wi-Fi access is available.

  • Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 118 reviews

    Set in Edgartown and only 1.2 km from Lighthouse Beach, Edgartown Commons Vacation Apartments offers accommodation with pool views, free WiFi and free private parking.

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 7 reviews

    Vineyard Escape offers accommodation in Vineyard Haven, 15 km from Edgartown Lighthouse. The property has a restaurant with an outdoor dining area.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 90 reviews

    Featuring free WiFi, The Christopher, The Edgartown Collection offers accommodation in Edgartown. The rooms include a flat-screen TV. Certain units have a seating area where you can relax.

    From US$401 per night
  • Vineyard Charm

    Edgartown
    8.0+ review score
    Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 5 reviews

    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.

Enjoy breakfast in Oak Bluffs and nearby

  • Brewster House

    Oak Bluffs
    Breakfast options
    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.

  • Scored out of 10, guest rating 7.3
    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.

  • 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.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 4 reviews

    Situated in Oak Bluffs, 100 metres from Oak Bluffs Town Beach and 10 km from Edgartown Lighthouse, Breezy Oak Bluffs Condo - Steps to Inkwell Beach!

  • Boasting air-conditioned accommodation with a patio, Captain Samuel Norris House is situated in Vineyard Haven. This beachfront property offers access to a balcony.

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

    Featuring accommodation with a balcony, Island Sanctuary is located in Oak Bluffs. Guests can benefit from a terrace and a children's playground.

  • Scored out of 10, guest rating 7.6
    Good - What previous guests thought, 15 reviews

    Main Street Upper enjoys a location in Vineyard Haven, just 400 metres from Owen Park Beach and 14 km from Edgartown Lighthouse. The property has a restaurant with an outdoor dining area.

  • Island Home

    Vineyard Haven
    Breakfast options
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 2 reviews

    Situated in Vineyard Haven, 200 metres from Owen Park Beach and 14 km from Edgartown Lighthouse, Island Home offers air conditioning. Spa facilities is available for guests.

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