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Holiday Rentals and Villas in Oak Bluffs, MA

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    280 Holiday Rentals in Oak Bluffs
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    £1,337
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    5 of 5 stars (2) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Sun filled and airy pond front contemporary home with beautiful views of Lagoon Pond. Four bedrooms accommodating up to eight guests. Two full baths plus refreshing outdoor shower. The second floor with its cathedral ceiling utilizes an open living room, dining room and kitchen floor plan to... View all property information
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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 15 August 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 6 August 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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    4 of 5 stars (1) Very good
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    About this property
    Fantastic vacation retreat! Steps to the Lagoon. Located on quiet street with fenced-in back yard. This perfect island vacation home has a relaxing back yard, comfortable floor plan, well-equipped kitchen and more. Enjoy the awesome beaches,great fishing, golf, and island ambience! Conveniently... View all property information
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    4 of 5 stars Reviewed 5 October 2014
    My husband and I spent 3 nights at this charming cottage. We liked the location, on a quiet residential street near the lagoon, yet not far from the center of town. We'd never...
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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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    1 / 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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    £267
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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 / 30
    5 of 5 stars (1) Excellent
    Overview Reviews (1)
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    • Balcony
    • Dishwasher
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    • Satellite TV
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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 1 October 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 / 17
    5 of 5 stars (1) Excellent
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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 27 August 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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    5 of 5 stars (1) Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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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 23 August 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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    £1,271
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    About this property
    Delightful summer cottage. Great family home for relaxing on the large deck, kayaking the lagoon, great play beach on the lagoon for children. The bunk house with two bedrooms is directly behind the main part of the house, about 10 steps across the yard. The views are spectacular and expansive.... View all property information
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    5 of 5 stars Reviewed 25 July 2014
    The house was perfect for our family. The views from the deck, family room and bedrooms were incredible. We ended up grilling 4 out of the 7 nights we were there because there is...
    5 of 5 stars Reviewed 18 July 2014
    I would love to say it was an awful stay so no one else would want to stay there but us, but truth be told - it was GLORIOUS. We so enjoyed sitting on the deck in the morning...
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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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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    £184
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    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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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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    £134
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    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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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    £401
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    1 / 44
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    • Dishwasher
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    • Pool Table
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    About this property
    *Fall/Winter/Spring multi-week discount available *Only 3 prime summer 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, bright and sunny, with a large... View all property information
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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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    £144
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    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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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    1 / 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 | Quick View
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    • Ocean Views
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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 25 October 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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 / 15
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
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    About this property
    Located in the Waterview Farm neighborhood. Immaculate contemporary with all the amenities. Located just off of the bike path and close to Farm Neck Golf Course. Miles of conservation land and walking trails to the waterfront. Association beach is a wonderful area for children to play and kayaking.... View all property information
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    £191
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    1 / 7
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Fireplace
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    • Waterfront
    • Water Views
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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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    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 15 February 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 16 December 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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    5 of 5 stars (1) Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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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 30 December 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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    4 of 5 stars (1) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pets allowed
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    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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    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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    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 11 August 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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    About this property
    Nestled in a private location on Crystal Lake which abounds with bird life, this is a delightful, vintage 1950's home with modern conveniences and comfortable furnishings. Its rambling single story layout is spacious and conducive to relaxed living. It is very well maintained and well equipped. The... View all property information
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    5 of 5 stars (3) Excellent
    Overview Reviews (3)
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    About this property
    Wonderful home located about a 10 minute walk to downtown Oak Bluffs. This home has a nice open floor plan for family gatherings, updated furnishings, fully equipped kitchen with stainless steel appliances, Master bath juccuzzi tub, Entertainment systems include flat screen TVs, CD, DVD, VCR,... View all property information
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    5 of 5 stars (3) Excellent
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    About this property
    Classic & charming, turn of the century 'campground' home situated on a 4,400 sq. ft. corner lot just a few minutes walk from the beach & town. Spacious & light rooms w/ some intimate spaces, a formal dining room, hardwood & pine floors, and a sweet porch all blend into a wonderful vacation spot.... View all property information
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This cozy, quaint waterfront property offers beautiful sunsets and great harbor views. Swimming, boating, kayaking, are just steps from this warm and charming quintessential Vineyard cottage. Amenities and Features include... Waterfront, Waterview Additional amenities include: dock/boat-slip,... View all property information
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    About this property
    This well maintained, vintage Victorian home is centrally located, yet away from the hustle and bustle of town: just one block from the beach, two blocks from Waban Park and Ocean Park, three blocks from tennis, backetball and a playground and four blocks from town. Enjoy the waterview of Vineyard... View all property information
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    5 of 5 stars (1) Excellent
    Overview Reviews (1)
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    About this property
    Located on over 1 acre of waterfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and friends that want to vacation together while maintaining their privacy. This home allows up to 4 families to stay together in the same home while giving... View all property information
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    5 of 5 stars (1) Excellent
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    About this property
    The quintessential Vineyard cottage!!! This sweet cottage brings back visions of the lazy days of summer of bygone eras when life was less hurried. The serene location overlooks a pond, a barrier beach with a few homes, and the Outer Harbor. It has a magnificent 180 degree view of Vineyard... View all property information
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    4 of 5 stars (2) Very good
    8 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    About this property
    A true Vineyard classic from 1890, this house retains its authentic charm yet has been thoughtfully renovated and serves the modern day vacationer well. The 8 bedrooms afford plenty of space to accomodate larger family groups for special reunions and vacations. The living room, sunporch and kitchen... View all property information
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    About this property
    Wonderful, spacious, lovingly maintained and attractive home in exclusive setting - family room with fireplace, large formal living room with fireplace, master bedroom with full private bath. Large kitchen and dining area that opens onto wonderful deck. Association tennis and boat landing on... View all property information
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    About this property
    Set back well off the road, this special Island home and it's surrounding open grounds are in a perfect mid-Island location for easy access to towns and beaches. It is very near to a wonderful bike path! The large living room has a tiny balconied and is graced by a an interesting, hand painted,... View all property information
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    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 19 August 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 10 August 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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    About this property
    The Blue Canoe is completely fresh and renovated, while its 1910 charm is fully intact. It has a lovely deck and a huge side yard surrounded by a split rail fence just perfect for enjoying summer lounging and games. The house is in a neighborhood central to many things including being just steps to... View all property information
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    About this property
    Wonderful Oak Bluffs home close to town and beach. This home has an open floor plan which is nice for relaxing with family and friends. Also enjoy the screened porch off the living area. Additional amenities include: coffee maker, lobster pot, cd player, wine glasses, heat, pillows, outside... View all property information
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    About this property
    Oak Bluffs Beach cottage. A/C.Classic Vineyard charm is what this cottage is all about. Enjoy watching the world go by from the porch rockers overlooking Nantucket Sound. Updated kitchen, dining room and living room with large windows with commanding views of the sound. And the deck is what a... View all property information
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    • Suitable for children
    • x
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    About this property
    Completely renovated cottage in the Sunset Lake area of Oak Bluffs. Walk to town and library. Completely renovated modern kitchen. Rock away on the large front porch. Additional amenities include: games, coffee maker, lobster pot, cd player, wine glasses, heat, fan(s), vacuum, ceiling fan(s),... View all property information
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    • ?
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    About this property
    This contemporary Cape, in a private setting, features a spacious, open, light, airy design with a wonderful large wrap-around deck. The bike path and MVTA (bus) are just a short ride/walk from the house. Two association tennis courts are an added plus! Additional amenities include: beach chairs,... View all property information
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    • Suitable for children
    • x
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    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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    About this property
    NEW FOR THE 2015 SEASON! BETTER PICTURES FORTHCOMING - HOUSE WILL HAVE ALL NEW FURNISHINGS AND FRESHLY PAINTED TO GIVE IT THAT VINEYARD BEACHY FEEL! PLEASE INQUIRE FOR MORE INFORMATION. Views, Views and more Views! Lovely water views of Sengekontacket Pond over the rolling 'forever' conservation... View all property information
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    5 of 5 stars (1) Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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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 14 October 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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