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Holiday Rentals and Villas in Oak Bluffs, MA

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    All 277 Rentals in Oak Bluffs
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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    From
    £922
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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    £4,941
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    5 Bedrooms / 4 Bathrooms / Sleeps 8
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    £1,911
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    1 / 17
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    £791
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    1 / 13
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Waterfront
    • Water Views
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    About this property
    OAK BLUFFS, Seaview condo: Immaculate second floor condo with porch overlooking Nantucket Sound. Beach,town,and bike path at your door. Window A/C. Additional amenities include: walktobeach, living room, dining cap: 6, city_c: oak bluffs, in-town, beach: state beach, baths: 2, waterfront desc.:... View all property information
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    £1,054
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    1 / 17
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    This charming home is situated in an idyllic private wooded setting on Sengekontacket Pond, one of the largest salt-water ponds on Martha's Vineyard. Comfortably furnished, it has a newlyr renovated kitchen and a new dining area overlooking Major's Cove. There is also a new screened in sun room for... View all property information
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    £2,306
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    1 / 19
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    This bright airy contemporary has wonderful views to the east and south over Sengekontacket Pond to Cape Pogue, with amazing sunrises.  To the west, enjoy the ever changing vistas of a 12 acre rolling meadow.  The walls of glass and interesting angles create a unique and inviting interior, with... View all property information
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    £207
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    1 / 24
    5 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Renovated beach house in Oak Bluffs with 5 Bedrooms, 2 full baths, Sleeps 8; Large living/dining room, sliding door opens to deck, flagstone picnic area with gas grill, A/C, Washer/Dryer, Free WIFI, Large flat-screen LED TV's with cable service; Located 10-20 min walk to Oak Bluffs harbor, beach... View all property information
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    £791
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    1 / 8
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
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    • Wheelchair access
    • Elder access
    • ?
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    About this property
    OAK BLUFFS, Seaview condo: Third floor water view condo with all ammenities and the beach across the street. Walk to town for great dining, shopping and night life. Additional amenities include: walktobeach, living room, dining cap: 4, bedrm2: 2 twins, dist. to beach: across street, beach: state... View all property information
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    £2,339
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    1 / 15
    6 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
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    About this property
    Situated on Farm Pond with views of the pond and Nantucket Sound is this charming summer house and guest cottage. Homes have antique charm with modern amenities. Located in Harthaven, you will have use of the neighborhood's private beaches and tennis. The main house has 4 bedrooms and 2.5 baths... View all property information
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    £198
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    1 / 5
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This 3.5 bedroom home with skylights, 52 inch Tv, computer, internet, printer, fax, is your home away from home. 1 mile from town 1.5 mile from beach and 7 miles from airport is ideal location. 2 SETS OF GOLF CLUBS AND 4 TENNIS RACQUETS FOR YOUR USE, 3 CABLE TV'S, MASTER BATH HAS WHIRLPOOL TUB... View all property information
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    £1,515
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    1 / 13
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Elder access
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    About this property
    OAK BLUFFS, Meadow View Farms: Contemporary salt box with open floor plan. Easy access to the bike path, Farm Neck for golf, and three miles to village center and the beach. Large deck overlooks the landscaped yard Additional amenities include: living room, tennis: assoc., dining cap: 8,... View all property information
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    £1,911
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    1 / 16
    7 Bedrooms / 3 Bathrooms / Sleeps 14
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    • Air Conditioning
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    • Satellite TV
    • Washer
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Classic, 'Camp Ground' over sized 7 bedroom 3 bath home in a residential neighborhood within easy walking distance to the beach, shops, restaurants, galleries, etc. It offers double master bedrooms (1st and 2nd floor.) Enjoy rocking on our huge front porch in over sized Georgia rockers. As you... View all property information
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    £1,021
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    1 / 17
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Pets allowed
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    About this property
    EAST CHOP HIDDEN GEM charming completely renovated cottage just a short stroll from the Marina, town, beaches, dining, shopping and nightlife which is what makes Oak Bluffs a destination vacation. Cottage features an open living kitchen and dining area, and full bath on the first floor. On the... View all property information
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    £692
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Internet Access
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    • Smoking allowed
    • Suitable for children
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    About this property
    'About Time' .......Treat your wallet to a vacation. Come to SECOND AVE; Quiet neighborhood, Great outdoor space. A/C Neat clean and tidy. Sleeps five. Walk to town, beach, and all that historic Oak Bluffs has to offer. A great value! First floor has the living room with flat screen TV and sleep... View all property information
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    £988
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    1 / 18
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Enjoy the charm of a Vineyard cottage with all the amenities of today. This 3 bedroom house has brand new furnishings for 2015. It is in a quiet neighborhood not far from Oak Bluffs center and its harbor. The house is also close to the bike path. The house has an open floor plan with a large... View all property information
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    £1,169
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    1 / 23
    5 Bedrooms / 2 Bathrooms / Sleeps 12
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    This house is located in a historic district, on a quiet side street, one block from downtown and within sight of the beach. On the first floor, there is a wrap around porch with seating for 12 in front, a comfortable living room, a nicely equipped eat-in kitchen, a dining room for 10-12 and a... View all property information
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    £1,943
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    1 / 14
    6 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
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    About this property
    The Pennacook house in Oak Bluffs on the charming island of Martha's Vineyard is beautifully maintained, bright and sunny, with a large eat-in kitchen, living room, dining room, and library with WIFI. Play outside on the large lawn, relax in the hammock, watch sunset from the front porch and enjoy... View all property information
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    £1,318
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    1 / 19
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Waterview Farm is a private association with wonderful meadow and water views.  It is adjacent to Farm Neck Golf Club, which is open to the public. There is access to Sengekontacket Pond to launch a canoe or kayak from the private association beach.  This is also a great spot for children to swim,... View all property information
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    £2,042
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    1 / 12
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    Located in Oak Bluffs this house is walking distance to town, the marina and nestled in the Copeland/Arts District area also walking distance to the historic Gingerbread cottages.  A 15 min. walk to the Inkwell beach and less than a 5 min. drive.  Four bedrooms and two full baths.  There is a nice... View all property information
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    £659
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    1 / 15
    4 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Tucked in a quiet neighborhood and within walking distance to town and beaches, this quaint cottage was moved to East Chop from the campgrounds at the turn of the century.  This simple yet charming and well-equipped bungalow has been in the same family for many years and is a lovely place for a... View all property information
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    From
    £1,087
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    1 / 12
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Grill
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    A charming early 1900s cottage in Oak Bluffs, just completely renovated. Walk to town, park, beach and steps to library. Two bedroom, one very large full bathroom. Spacious working, eat-in-kitchen with all stainless steel appliances and washer/dryer. Separate dining area. Cable, TV, Wi-fi, Ipod... View all property information
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    £1,515
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    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • x
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    • Elder access
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    About this property
    Wonderful water views from this second floor end condo. Located right across the street from State Beach, this condo is within walking distance to the center of Oak Bluffs. Beautifully furnished and appointed, you can enjoy your vacation and leave your car at home. View all property information
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    £1,812
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    1 / 17
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Suitable for children
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    About this property
    East Chop Gem~Sweet East Chop cottage perfectly appointed and beautifully kept. 2 Bedrooms, plus finished basement with sleeper sofa allow for plenty of room to rest and play.Downstairs ping pong, over-sized deck and forest views make this cottage fun and inviting. 1 full bath, and 1/2 bath, walk... View all property information
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    £1,318
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    1 / 14
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Waterview Farm is a private association with wonderful meadow and water views. It is adjacent to Farm Neck Golf and Tennis Club, which is open the public. There is access to Sengekontacket Pond to launch canoes and kayaks from the private association beach. This is also a great spot for children to... View all property information
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    £1,318
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    1 / 22
    5 Bedrooms / 4 Bathrooms / Sleeps 10
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Our 'treehouse' is the tallest residence in the town of Oak Bluffs. Enjoy quiet and seclusion in this wooded setting, located in the exclusive Meadow View Farms community. There are panoramic views from the upper level, above the treetops. The bike path and MVTA (bus) are steps from the door, and... View all property information
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    £165
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    1 / 25
    2 Bedrooms / 1 Bathroom / Sleeps 7
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    • Air Conditioning
    • Balcony
    • Dryer
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    • Washer
    • Water Views
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    DESCRIPTION: Water view on Brush Pond, sleeps 7. Open concept 1st floor living area w/sleep sofa, dining area, open galley kitchen, queen bedroom, full bath. Entire 2nd floor enclosed loft queen bedroom with daybed and balcony overlooking water. Huge furnished deck, big yard and private driveway... View all property information
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    £132
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    1 / 23
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Grill
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    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
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    About this property
    FEATURES: Charming cottage hide-away sleeps 6 on 3 private acres, conveniently located. Walk to beach, 1 mi from 2 harbor towns, groceries, shops, dining, nightlife, and bike, car, watercraft rentals. Bike path access from property. Bus stops nearby with transit service to all island towns, beaches... View all property information
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