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Oak Bluffs, Massachusetts Vacation Rentals | ClearStay.com

Oak Bluffs, Massachusetts Vacation Rentals

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  • WARC13F

    $115-$229 per night*

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

    Location:
    Oak Bluffs
    Bedrooms:
    3 
    Bathrooms:
    1 
    Max. Guests:
    4 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • BELT321

    $115-$300 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    3 
    Bathrooms:
    2 
    Max. Guests:
    6 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • BASL107

    $115-$358 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    2 
    Bathrooms:
    2.5 
    Max. Guests:
    8 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • HECC137

    $125-$232 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    1 
    Bathrooms:
    1 
    Max. Guests:
    2 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • ANTH44T

    $129-$172 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    1 
    Bathrooms:
    1 
    Max. Guests:
    2 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • DAVN60H

    $129-$258 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    2 
    Bathrooms:
    1 
    Max. Guests:
    4 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • TUCL3AH

    $136-$222 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    2 
    Bathrooms:
    1 
    Max. Guests:
    3 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • DARA37F

    $136-$250 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    2 
    Bathrooms:
    1 
    Max. Guests:
    6 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • BARN125

    $143-$178 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    1 
    Bathrooms:
    1 
    Max. Guests:
    2 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • DOMN55M

    $143-$186 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    2 
    Bathrooms:
    1.5 
    Max. Guests:
    4 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • LUCG59B

    $143-$215 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    3 
    Bathrooms:
    1 
    Max. Guests:
    6 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • DIAD320

    $143-$229 per night*

    Charming home in West Tisbury. Quiet setting in the woods and a short walk to Vineyard Food Shop. Picture perfect for small family.

    Location:
    Oak Bluffs
    Bedrooms:
    2 
    Bathrooms:
    1 
    Max. Guests:
    5 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • DONS5BR

    $143-$258 per night*

    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.

    Location:
    Oak Bluffs
    Bedrooms:
    3 
    Bathrooms:
    1 
    Max. Guests:
    6 
    Pets:
    No Pets 
    Type:
    Hotel 
  • LARJ13C

    $143-$258 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    2 
    Bathrooms:
    2 
    Max. Guests:
    5 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • MONA100

    $143-$258 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    3 
    Bathrooms:
    1.5 
    Max. Guests:
    6 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • QUIN18K

    $143-$308 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    3 
    Bathrooms:
    2.5 
    Max. Guests:
    6 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • GOL12M

    $143-$315 per night*

    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,…

    Location:
    Oak Bluffs
    Bedrooms:
    4 
    Bathrooms:
    2 
    Max. Guests:
    8 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • SACS467

    $143-$315 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    3 
    Bathrooms:
    2.5 
    Max. Guests:
    6 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • STAS400

    $143-$372 per night*

    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…

    Location:
    Oak Bluffs
    Bedrooms:
    4 
    Bathrooms:
    2 
    Max. Guests:
    7 
    Pets:
    No Pets 
    Type:
    Vacation Home 
  • GIBT25N

    $143-$422 per night*

    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,…

    Location:
    Oak Bluffs
    Bedrooms:
    4 
    Bathrooms:
    2 
    Max. Guests:
    9 
    Pets:
    No Pets 
    Type:
    Vacation Home 
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*Final rates are based on travel dates and other factors.

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