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Vacation Rentals in Oak Bluffs, Massachusetts

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  • A true vintage beach cottage, just a stroll to the town beach. Simple, quaint - a perfect summer experience.

    $115-$229 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 4
    • 3 bedrooms,
    • 1 bathroom
    • No Pets
  • This Cape is charming, spacious and private. Access to Association tennis, pool and bike paths. Fully equipped gourmet kitchen and sun room open to large 30x12 rear deck. Hardwood floors throughout…

    $115-$300 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 6
    • 3 bedrooms,
    • 2 bathrooms
    • No Pets
  • Newly built cottage-style home, charming, comfortable and well furnished home. Convenient location to grocery store, library, playground and a short drive to Long Point and Lambert's Cove beach. Open…

    $115-$358 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 8
    • 2 bedrooms,
    • 2½ bathrooms
    • No Pets
  • Charming small cottage, completely renovated with hardwood floors. Light and airy with island decor. Great location, short walk to town and close to beach. Deck out back. Main house occupied by owner…

    $125-$232 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 2
    • 1 bedroom,
    • 1 bathroom
    • No Pets
  • Peaceful cottage nestled in the reeds. Perfect long term rental for an individual or couple. Watch the sunset from the roof deck and the ferry come and go. Walk, bike or take the bus to town and…

    $129-$172 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 2
    • 1 bedroom,
    • 1 bathroom
    • No Pets
  • Great location in lovely neighborhood with private beach access. Well maintained two bedroom, one bath ranch. Recently renovated and attractively furnished. New kitchen, new hardwood floors and…

    $129-$258 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 4
    • 2 bedrooms,
    • 1 bathroom
    • No Pets
  • Wonderful, charming cottage at the edge of the Lagoon with private beach. Incredible views, nicely maintained lawn and perennials garden. Located in a desirable area on the outskirts of town, walk to…

    $136-$222 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 3
    • 2 bedrooms,
    • 1 bathroom
    • No Pets
  • Cozy and comfortable two bedroom home with open living area and large outdoor deck. Convenient location, approximately 0.5 miles to ferry, town and shopping. Great for a small family. A short walk to…

    $136-$250 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 6
    • 2 bedrooms,
    • 1 bathroom
    • No Pets
  • Sunny one bedroom apartment built in 2005. Bright, open living area with new furnishings and appliances throughout apartment. Located on a nice private residential street. Convenient to town, ferry…

    $143-$178 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 2
    • 1 bedroom,
    • 1 bathroom
    • No Pets
  • This lovely two bedroom cottage has hardwood floors, fully equipped kitchen, a wrap around deck, sunshine and lots of charm. Centrally located, in a quiet neighborhood, within walking distance to the…

    $143-$186 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 4
    • 2 bedrooms,
    • 1½ bathrooms
    • No Pets
  • Charming cottage with three bedrooms. Close proximity to Lagoon Pond with Brush Pond waterview. Located in a quiet neighborhood, dead end street. Approximately 1-2 miles to Oak Bluffs center for…

    $143-$215 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 6
    • 3 bedrooms,
    • 1 bathroom
    • No Pets
  • Charming home in West Tisbury. Quiet setting in the woods and a short walk to Vineyard Food Shop. Picture perfect for small family.

    $143-$229 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 5
    • 2 bedrooms,
    • 1 bathroom
    • No Pets
  • Charming three bedroom one bath fully equipped home located in Edgartown Estates. Relax and unwind outdoors on the large wrap around deck. There's also an enclosed outdoor shower for your convenience.

    $143-$258 per night*
    • Oak Bluffs
    • Other
    • Sleeps 6
    • 3 bedrooms,
    • 1 bathroom
    • No Pets
  • Cozy, sunny, newly renovated contemporary Ranch conveniently located in Edgartown on a cul-de-sac. Lovely private fenced back yard and deck with both living room and master bedroom access via sliding…

    $143-$258 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 5
    • 2 bedrooms,
    • 2 bathrooms
    • No Pets
  • Sunny, comfortable three bedroom home with screened in porch and private back yard. Great location, just a short walk to town, restaurants, shops and ferry. Close to lake Tashmoo, town landing and…

    $143-$258 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 6
    • 3 bedrooms,
    • 1½ bathrooms
    • No Pets
  • Reverse contemporary home, overlooking conservation land and distant waterview. Large second floor deck, great for relaxing and enjoying outdoor family time. Private setting, over half acre near bike…

    $143-$308 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 6
    • 3 bedrooms,
    • 2½ bathrooms
    • No Pets
  • Located in prestigous Major's Cove, easy access to all three down-island towns. Large four bedroom, two bath with skylight and vaulted ceilings. Walking distance to Sengekontacket Pond for kayaking,…

    $143-$315 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 8
    • 4 bedrooms,
    • 2 bathrooms
    • No Pets
  • Just a short walk to beautiful South Beach, this three bedroom townhouse is furnished for comfortable summer living. The large private deck is a perfect place to relax after a day at the beach. Enjoy…

    $143-$315 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 6
    • 3 bedrooms,
    • 2½ bathrooms
    • No Pets
  • Renovated cottage overlooking Menemsha Pond and Lobsterville. Excellent location just a few steps to the village and beach. All new appliances: dishwasher, washer/dryer, refrigerator. Great vacation…

    $143-$372 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 7
    • 4 bedrooms,
    • 2 bathrooms
    • No Pets
  • Spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. House is fully equipped, open living area with cathedral ceilings, wood floors,…

    $143-$422 per night*
    • Oak Bluffs
    • Vacation Home
    • Sleeps 9
    • 4 bedrooms,
    • 2 bathrooms
    • No Pets
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*Final rates are based on travel dates and other factors.

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