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Cottages and house rentals in Oak Bluffs, MA

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    $175
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    1 / 8
    4 of 5 stars (1) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    $2,000
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    6 Bedrooms / 3 Bathrooms / Sleeps 14
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    5 Bedrooms / 3 Bathrooms / Sleeps 16
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Home away from Home! Walk to Sailing Camp! Bright, sunny 3 bedroom Cape style vacation home in Lagoon Heights with great amenities. Fully furnished home with 2 baths, outdoor shower, large deck and private enclosed yard and a wonderful deck for the summer cookouts. Open floor plan with spacious... View all property information
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    1 / 9
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Our comfortable, reverse contemporary home has 2 bedrooms on the first floor (one with a full size bed and one with a twin), a 3/4 bath with shower, as well as a family room with a fold-out futon couch. Upstairs on the second floor, our home has an open design with a bright kitchen/dining/living... View all property information
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    1 / 16
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    This property will rent year year round weekly, please inquire for rates. This bright and spacious home is conveniently located just minutes from all down-island towns yet in a peaceful neighborhood surrounded by conservation trails and farmland.  The entire house has been newly decorated with... View all property information
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    $140
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    1 / 20
    5 of 5 stars (4) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    This spacious condo is an ideal vacation rental for a small family, a couple or two couples looking for clean, comfortable accommodations with the amenities needed to ensure a relaxed vacation. This large 2 bedroom end unit (1200 sq ft + large deck) is bright and airy. Downstairs has new hardwood... View all property information
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    5 of 5 stars Reviewed August 15, 2014
    We just finished our MV vacation and we had a great time. The condo is perfectly located between Edgartown, Vineyard Haven and OaksBluff. The bike trails are literally right out...
    5 of 5 stars Reviewed August 5, 2013
    We had a great relaxed vacation at this condo. It is a quiet and in a scenic and greenery neighborhood. The two-story apartment is perfect for a couple and small family with 3-4...
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    1 / 38
    5 of 5 stars (5) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    This welcoming home is freshly renovated and decorated in calm and comfortable Vineyard style, with hand-hewn, antique and designer furnishings. The house is ideally located on a quiet street, within easy walking distance to the village, harbor, beaches, waterfront parks and historic Victorian... View all property information
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    5 of 5 stars Reviewed December 16, 2014
    Comfortable, cozy, quiet and convenient. Very cute decor, clean and spacious. We loved our stay here.
    5 of 5 stars Reviewed September 20, 2014
    A great time was had by everyone! This house was exactly as described but the best part was dealing directly with the owner and knowing that they were only a phone call away if...
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    1 / 23
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This lovely 3 bedroom home features an open floor plan on the living level, colorful decor, window ac in all rooms and a well equipped modern kitchen. The home is nicely situated in quiet neighborhood, on the outskirts of Oak Bluffs, convenient to all three down island towns and beaches and a short... View all property information
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    $400
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    1 / 30
    5 of 5 stars (1) Excellent
    6 Bedrooms / 2 Bathrooms / Sleeps 13
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    • Balcony
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    • Water Views
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    About this property
    *6 bedrooms, 2 full bathrooms + outdoor shower, sleeps 13 *1800+ sq. ft of living space (fully renovated and freshly painted) *2 NEWLY REBUILT BEDROOM-BALCONIES, 1 w/ a water-view - beautifully restored! *400 sq. ft wrap-around front porch with water view and comfortable seating for 11+ (4 rocking... View all property information
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    5 of 5 stars Reviewed September 30, 2014
    Favorite things were outdoor shower and front porch (with rocking chairs and great dining table area). Great location - walking distance to the water (which you can see from...
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    1 / 7
    3 Bedrooms / 1 Bathroom / Sleeps 7
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    About this property
    A comfortable ranch with all the amenities for a perfect vacation. It's quiet location is 1.5 miles from town, yet not too far to bike or walk in when needed. Beaches, ponds, the lagoon, and other recreational facilities are also easily accessible if you want to hop on the bike path around the... View all property information
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    $400
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    1 / 11
    4 Bedrooms / 1 Bathroom / Sleeps 8
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    About this property
    New Renovated, 1870 historic 'Campground' cottage centrally located in Oak Bluffs, The cottage has 4 bedrooms (all located on the second floor) - 1 queen, 2 double beds and 2 twins beds. The front bedroom has its own balcony with water views. Cottage sleeps 8. the first floor includes a newly... View all property information
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    1 / 17
    5 of 5 stars (1) Excellent
    4 Bedrooms / 1 Bathroom / Sleeps 8
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    About this property
    This is an old farmhouse consisting of 2 floors with 3 bedrooms on the second floor and 1 on the first floor. One queen and 3 doubles. A large living room and bath on the first floor. In the kitchen is a Refrigerator, gas stove with oven, a washer and dryer and a dishwasher. There is a portable... View all property information
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    5 of 5 stars Reviewed August 22, 2014
    So often descriptions fall short of reality but our stay at this Flip-key rental was as it was toted, a "Charming Farmhouse." The four bedrooms were sweet and spacious decorated...
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    1 / 10
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The... View all property information
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    1 / 17
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    Sweet two bedroom cottage with everything you need for that perfect vacation on the vineyard. Imagine walking the sandy beach on a glorious vineyard summer day. Bike or drive to Oak Bluffs, Edgartown is close and there is also golf, shopping and great restaurants minutes away. You will remember... View all property information
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    $275
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    1 / 6
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Water Views
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    • Pets allowed
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    • x
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    About this property
    This cottage is the perfect getaway for a stay on Martha's Vineyard. It has been painted, polished and newly furnished. There is a great deck, grill and best of all a private outdoor shower. King size bed and 3 twins in the two bedrooms upstairs. Galley kitchen, living and dining area on first... View all property information
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    $225
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    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This bright and charming 3 bedroom, 1.5 bath house rests outside downtown Oak Bluffs. The house boasts 3 bedrooms, 1.5 baths, an open living room/kitchen combination, 2 decks and an outside eating area. The first floor bedroom contains a full sized bed. A half bath with laundry is across the... View all property information
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    5 of 5 stars Reviewed August 27, 2013
    Stayed in this cute little house with 6 adults and 2 children. It was perfect! It is within walking distance to downtown OakBluffs. Walked there every morning and back to the...
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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This airy home captures the spirit of easy island life and makes you feel like you've gotten away. It's secluded on a quiet, wooded, paved, dead-end street, the second house from the end. Yet it's centrally located in the East Chop area of Oak Bluffs for easy access to the beaches (.25 miles to... View all property information
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    $450
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    1 / 44
    6 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    *New lower Winter/spring rates only $1200/week! *multi-week discount available *Only 3 prime summer 2013 weeks left! Check my calendar and book ASAP if you plan to visit in the peak season. The Pennacook house in Oak Bluffs on the charming island of Martha's Vineyard is beautifully maintained,... View all property information
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    $1,800
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    1 / 13
    3 Bedrooms / 1 Bathroom / Sleeps 7
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    About this property
    Steps to town and harbor, this newly renovated home offers the perfect location for families looking for modern convenience at a great rate. Guest house also available for up to four additional guests at additional rate. The outdoor free-standing shower is shared with guest house. Additional... View all property information
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    $2,550
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    1 / 9
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Beautiful and spacious 3 bedroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape. Walking distance to town, gingerbread cottages, library, and playground. Close to beach, golf course, and great fishing spots. There is a pack and play in the upstairs bedroom for a baby to sleep or nap... View all property information
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    $600
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    1 / 9
    5 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Waterfront
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    About this property
    Across the street from the renowned Inkwell beach and just minutes to walk to town, harbor and the ferry. This large classic victorian beach house was built in 1851. The property has a beach studio next door which can be rented for larger groups. A large classic wrap around porch with ocean... View all property information
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    1 / 26
    5 of 5 stars (1) Excellent
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Balcony
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    • Ocean Views
    • Washer
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    • Pets allowed
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    • Suitable for children
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    About this property
    5 BR, 2 full BA, 2 half BA, sleeps 10 Recently renovated Victorian home located in the historic Copeland District just one block from Oak Bluff's Inkwell beach. Three story home with decks and wrap around porch with ocean views from each. Five large bedrooms, spacious living room with brick... View all property information
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    5 of 5 stars Reviewed October 25, 2014
    We stayed here in June of 2014 and had a great time. The house sleeps 10 people comfortably so it's nice for two families or a large extended family. It is steps from two beaches...
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    $285
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    1 / 7
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Fireplace
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    • Waterfront
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    • Pets allowed
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    About this property
    Martha's Vineyard: $1,995per week. Week of June 28th available and July 5 through July 19 Beautiful Waterfront Cottage with magnificent sunsets over Vineyard Haven harbor. Watch the vivid changing colors in the sky at the end of every day. Fish off the Beach and cook your catch on the grill. The... View all property information
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    1 / 13
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    This contemporary farmhouse is located in the quiet Bayes Hill area of Oak Bluffs. From its classic farmer's porch to wraparound bay windows to comfortable living spaces, there is nice detailing throughout the comfortable four bedroom house. The association tennis court is just down the road, and... View all property information
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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This charming Cape style Oak house residence is situated on a wooded lot near bike path and just a short ride to town center and ferry. This home features an open design with a bright kitchen/dining/living area with hardwood floors, den and full bath on the first floor. Sliders in the dining area... View all property information
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    1 / 20
    5 of 5 stars (41) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Water Views
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the middle of the most active, multi-cultural, charming, and fun town on Martha's Vineyard. Step outside your door for breakfast or ice cream, a great selection of restaurants in... View all property information
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    5 of 5 stars Reviewed February 15, 2015
    I come stay here every year and cannot get enough. It is so centrally located - on the main street in Oak Bluffs, near the ferry, fishing charters, beaches, running trails, and...
    5 of 5 stars Reviewed December 15, 2014
    My family loves the central location of this property! The front porch provides loads of free entertainment! The BEST spot!
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    1 / 10
    4 of 5 stars (5) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Safe
    • Satellite TV
    • Waterfront
    • Water Views
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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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    • x
    About this property
    Come Stay aboard Martha's Vineyard's ONLY FLOATING Bed and Breakfast! Celebrating our 5th season!! MS Resolute is a classic 40 ft Islander Cutter Sailboat docked at the picturesque Oak Bluffs Marina. Experience a unique boating adventure without ever leaving the dock. Enjoy romantic sunsets, be... View all property information
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    5 of 5 stars Reviewed August 18, 2014
    My husband and I just returned from a 3 night stay on the Resolute - Bed and Breakfast Afloat and had a wonderful time. We took the Island Queen ferry in from Falmouth and had...
    3 of 5 stars Reviewed August 10, 2014
    My girlfriend and I stayed here for 4 nights. The place is charming and Susan and John the host and hostess very gracious. We were blessed with great weather. Sitting on the...
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    $270
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    1 / 7
    5 of 5 stars (1) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Dryer
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    About this property
    Our picture-perfect home is an excellent summer escape. Spacious double lot makes this setting seem like a parkland. It's just a 15-minute walk to downtown Oak Bluffs and the town beach. It's also on the public transit line and the bike path. View all property information
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    5 of 5 stars Reviewed December 30, 2014
    I stayed at this house for a weekend this past June. It was perfect: close to the Ferry, fit 6 of us, has a private backyard. We were out and about most of the time, during the...
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    1 / 26
    5 of 5 stars (1) Excellent
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    Cinderella Cottage ~ Charming Oak Bluffs Victorian located walking distance to town and two blocks to the beach.  Not right on the main road but so close to everything! The house has four spacious bedrooms, three baths, a well equipped kitchen, two living rooms and a very nice dining room. There is... View all property information
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    5 of 5 stars Reviewed October 14, 2013
    We stay at the Pequot every year for Columbus Day weekend and we will keep coming back for as long as we are able! We have a great family reunion here every year, where family...
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    1 / 9
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    • Elder access
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    About this property
    4 bedrooms.3 baths, sleeps 8 The house is tucked away on a quiet, homey road, just a short walking distance to Circuit Avenue – the hub of Oak Bluffs activity! Here, you will enjoy the best of both worlds; whether you prefer to relax in the quiet, inviting and comfortable surroundings of this four... View all property information
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    4 of 5 stars (1) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    This deluxe waterside home has been recenty renovated from top-to-bottom, combining today's finest amenities and vintage mission-style charm, with a design that provides water views from all its rooms. The Mission House is uniquely situated with two water views. From the front, it sits directly... View all property information
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    4 of 5 stars Reviewed February 15, 2015
    We rented this home in August 2014 for two weeks. We are a family of 5 including my mother. This house has undergone a complete renovation. There is a lovely open kitchen that...
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    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Elder access
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    About this property
    With Inkwell Beach at your door step, sweeping ocean views from your private deck and Living Room, and walk-to-town convenience, this Waterside Condo offers a unique vacation getaway in Oak Bluffs. Located directly across the street from popular Inkwell Beach, the second floor condo enjoys sweeping... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Elder access
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    About this property
    This lovely and secluded retreat is perfect for those looking for an enjoyable vacation away from the summer crowds. Bridle Path is a wooded, rolling hill section of Oak Bluffs, located near some prominent farms and horse stables. This custom-built home features top-quality furnishings and... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    • ?
    About this property
    Newly renovated and painted campground victorian home with gingerbread accents. This charming victorian is ideally located close to town, shops, restaurants and beaches. Enjoy peeks of the harbor while watching the sunset from the new roof top deck. Additional amenities include: coffee maker,... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This charming cape style residence is situated on a wooded lot near the bike path and just a short ride to town center and the ferry. The home features a first floor open design with a bright kitchen / dining / living area and hardwood floors. The first floor den has a full size bed and French... View all property information
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    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    About this property
    Beachfront living combined with the convenenience of in-town. This condo makes your Vineyard vacation easy. Enjoy sweeping ocean views of Nantucket Sound and Chappaquiddick, with Oak Bluffs' popular Inkwell Beach directly across the street. Enjoy a second floor condo with water views from the... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    You are just steps from Circuit Avenue, Oak Bluffs Harbor and the beach from this comfortable in-town apartment in an exclusive small building. The sun-filled great room has open living and dining areas, and a well-equipped kitchen. The two bedrooms are also on the main floor. Stairs lead up to a... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    Quietly tucked away in prestigious Farm Neck Golf Club, this contemporary has sweeping waterviews of Sengekontacket Pond, State Beach and the Atlantic, as well as the 8th hole on the golf course. Situated on almost two landscaped acres, there are large wrap-around decks that afford multiple... View all property information
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    4 of 5 stars (1) Very good
    5 Bedrooms / 4 Bathrooms / Sleeps 13
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    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    • x
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    About this property
    Newly renovated 5 bedroom home just a mile and a half from the center of Oak Bluffs. New hard wood floors throughout as well as updated furnishings and decor. Dining area is extended by a nice sized sunny deck for outdoor dining. Perfect for a large family vacation. Additional amenities include:... View all property information
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    4 of 5 stars Reviewed August 11, 2013
    Nice, clean, updated home with space for everyone. We divided older teen girls in upstairs dorm style rooms that slept 5 from you get boys and girls in two rooms that slept 2 and...
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • ?
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    About this property
    Tucked away on the shores of The Lagoon, this deluxe waterfront retreat has been designed with an open layout to maximize grand water views and sunsets from its decks, screened porch and most rooms. The main level of Crow's Nest features a stylish wrap-around mahogany deck, and Great Room with open... View all property information
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    1 / 15
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Elder access
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    About this property
    All of Oak Bluffs at your fingertips and a front row seat for the beach. From your private deck, watch sunrise over Nantucket Sound with beach views along Inkwell Beach. Downtown's restaurants, shops, attractions, and ferry are just a short stroll away. This beachside condo is designed to maximize... View all property information
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    7 Bedrooms / 6 Bathrooms / Sleeps 14
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    About this property
    Perfect for family and friends that want to vacation together, while maintaining their privacy, this unique home allows up to four families to stay together in the same home, while giving each of them total privacy. This 4,000-square-foot, seven-bedroom, six-bathroom home is located on over one... View all property information
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    1 / 27
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    This waterfront luxury retreat, designed by Hutker Architects, sits quietly perched above the Lagoon, with a large pool, private beach and sweeping water views. 'Sandy Point' takes its name from the unique private beach below with its prominent point of sand that juts out into the Lagoon. Private... View all property information
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    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Modern, spacious, family friendly home, located 250 steps from the Lagoon beach for swimming, clamming, boating, beaching, and sunset watching.The main floor has a granite kitchen, open living and dining area, 1/2 bath with laundry facilities and master bedroom with shower and deck. The second... View all property information
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    5 of 5 stars Reviewed July 4, 2014
    Stayed at this house for a week with my wife and two young children. Very easy to get to and is a five minute drive to downtown Oak Bluffs and ten minutes to State Beach. Very...
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    4 Bedrooms / 3 Bathrooms / Sleeps 9
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    About this property
    Located on almost two waterfront acres, this beach house sits directly on the shores of The Lagoon, with its own private sandy beach and water views of The Lagoon and beyond to Nantucket Sound. The Beach House On The Lagoon is designed around the water views, with large wraparound deck, screened... View all property information
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    Set in a quiet section of Meadow View Farms, this contemporary farmhouse is nicely styled throughout and conveniently located between Oak Bluffs and Vineyard Haven. The first floor features a large Living Room with vaulted ceiling, fireplace, media center, and sliding doors to the back deck and... View all property information
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    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    About this property
    This newly built Farm Neck home features quality craftsmanship, impeccable furnishings and water views from most rooms. The home is nestled within the Farm Neck Golf Course and faces south, overlooking Sengekontacket Pond. A dramatic two-story Great Room opens out to a bluestone patio that expands... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    About this property
    Tucked away in a quiet area of Oak Bluffs, this stylishly renovated beach cottage is designed around its glistening water views. The Hideaway sits on the shore of Farm Pond with Atlantic Ocean views across Nantucket Sound to Chappaquiddick. A wall of sliding glass doors brings the water views into... View all property information
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    4 of 5 stars (1) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • x
    • ?
    About this property
    Come experience the magic of the Vineyard in our island home. Modernized in 2011, this charming residence is clean, cozy and boasts new furniture and decor. Amenities include 3 TV’s, cable television, Wi-fi, DVD, telephone, I-home, and Keurig Coffee maker. The property has a private yard, sundeck,... View all property information
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