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Vacation Rentals in Vineyard Haven, MA

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    $220
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    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    1 / 9
    4 of 5 stars (1) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    3 Bedrooms / 4 Bathrooms / Sleeps 7
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    1 / 7
    4 Bedrooms / 3 Bathrooms / Sleeps 10
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    About this property
    Four bedroom, two and half bath vacation rental perfect for one or two families or a group of friends. Comfortably sleeps 10. Modern house built in 2007 with central air. Two 2 person kayaks provided with paddles, life jackets, and all necessary equipment. Private trail to Tashmoo Pond with... View all property information
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    1 / 14
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    This unit is part of Charles and Charles MV, intimate Inn and guest apartments. We accept children over the age of 10. Edgartown Suite: This 2nd floor unit located in the guest house has two private entrances. It is our largest unit with over 1100 square feet. This unit has a fully stock kitchen... View all property information
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    5 of 5 stars Reviewed August 19, 2014
    There's really nothing much that hasn't already been raved about by other reviewers. Just the fact that Charles and Charles has become the Number 1 B&B in Vineyard Haven in only...
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    1 / 23
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    A rare find on the Vineyard -- true ocean and beachfront living. The Cottage at The Beach sits directly on the sandy shores of Vineyard Sound with panoramic views of the entire Sound, including the Elizabeth Islands and Woods Hole. In the other direction, sweeping sunrise views of Lake Tashmoo. The... View all property information
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    1 / 18
    5 of 5 stars (21) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    HIGHEST RATED MARTHA'S VINEYARD VACATION RENTAL ON FLIPKEY.COM! This comfy, beachy three bedroom home is located on a quiet, private street in Vineyard Haven. Convenient location, just a half mile from town beach and a mile from downtown shops, ferry and Owen Park. Comfortable and new furnishings... View all property information
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    5 of 5 stars Reviewed October 17, 2014
    Todd was great to deal with from the start. I was Completely impressed with how everything at the home was set up so perfect . From games to CDs , to DVDs and anything you need...
    5 of 5 stars Reviewed August 17, 2014
    The whole family had a great time! Karla and Todd are terrific to work with- very responsive to every question we had. They thought of everything you will need for a great...
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    $149
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    1 / 8
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    3 Bedroom, 1 Bath Ranch, In Quiet Neighborhood Close To Beach And Town. Just completed renovation, be the first to stay here! Fantastic island retreat, completely remodeled in 2014. Gleaming hardwood floors, granite counter tops, new appliances, tiled bath and 42 inch flat screen tv, and free wifi... View all property information
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    1 / 17
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
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    About this property
    Summer 2015!!! Beautiful, handcrafted, furnished 2300 sq. ft., 2 1/2 bath, four bedroom house on Martha's Vineyard which is handicap accessible. Our house is located in the woods in Vineyard Haven, with porch, yard and back deck with plenty of sunshine. A private sylvan setting surrounded by... View all property information
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    1 / 7
    5 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Grill
    • Internet Access
    • Satellite TV
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    • Pets allowed
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    About this property
    This home is in a quiet residential, tree-lined neighborhood on a dead-end street just about a mile from downtown Vineyard Haven and on the bike path and bus route. Formerly owned by an island artist, this 5-bedroom home features a number of creative touches - from handmade switch plates and... View all property information
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    $275
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    1 / 4
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
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    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    • Water Views
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    About this property
    Beautiful two bedroom poolside condo in Vineyard Haven. Fully equipped with cable and WiFi included. Short walk to town and ferry. Playground and basketball court close by. Bike racks, barbeque grills, manicured grounds, and coin operated laundry for guests and owners. View all property information
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    1 / 59
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    It's everything that is wonderful about the Vineyard! A private up-island feel that's still close to town and restaurants. Three bedrooms and a sleeping loft sited beautifully on 3 acres with access to hundreds of acres of private farm land. Recent renovations include new bathrooms, appliances,... View all property information
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    $500
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Wi-Fi
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    • Pets allowed
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    About this property
    Our 1920's home in Vineyard Haven is quaint and full of character. The house is walkable to town (including grocery store, hardware store, bike rental shop, restaurants, shops and more) and features a fully equipped and recently renovated kitchen, indoor front porch with daybed/pull out trundle,... View all property information
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    $1,875
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    1 / 28
    5 of 5 stars (2) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
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    About this property
    Built in 2006, Our home has the beauty of a Bird Sanctuary across from it and only a 1/2 mile from Town and the Beach. Being at the end of our road offers privacy and parking. There are 3 bedrooms and each has their own private full bathroom. The 1st floor has one bedroom which allows you to... View all property information
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    5 of 5 stars Reviewed September 8, 2014
    Janine and Barry's house is lovely, quiet and comfortable. Its a few minutes drive outside of Vineyard haven on a quiet dirt road. House/kitchen have everything you'd need...
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
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    About this property
    Located on a quiet residential circle in Vineyard Haven, this home with oversized windows is contemporary yet rustic with exposed wooden beams and a cathedral ceiling. New natural travertine floors unify the open and light filled freshly painted and fully appointed kitchen, dining, and living room... View all property information
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    1 / 19
    5 of 5 stars (10) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
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    About this property
    The guest house has a queen bed upstairs (large combination master suite/living room with vaulted ceiling, ceiling fans and walk out to deck) and bedroom with 2 twins downstairs, bathroom on first floor, AC throughout the house (central downstairs and remote controlled mini split upstairs),... View all property information
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    5 of 5 stars Reviewed September 22, 2014
    We had such a great time during our stay at David's guest house. The location could not have been any more perfect as it was a nice quick walk from the Vineyard Haven ferry. David...
    5 of 5 stars Reviewed June 22, 2014
    Thoroughly enjoyed our stay at this home in Vineyard Haven! It was not far from the boat dock we arrived at and it was close to town. Everything we needed was supplied at the...
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    $860
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    1 / 19
    5 of 5 stars (1) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Recently renovated home in prestigious Lower Makonikey. Water views of Vineyard Sound. On private 3 acre lot. Short walk through the woods to private beach. Two master bedrooms, Jacuzzi and recreation area with horseshoes and volleyball. Fully air-conditioned and equipped for a perfect vacation.... View all property information
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    1 / 8
    5 of 5 stars (5) Excellent
    5 Bedrooms / 3 Bathrooms / Sleeps 9
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    • Dishwasher
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    • Grill
    • Internet Access
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This sweet Vineyard Haven home blends historic character with fresh and tasteful upgrades throughout. With a focus on comfort and amenities, this charming home is a delightful place to call home. Additional amenities include: beach chairs, beach towels, coffee maker, electric mixer, lobster pot,... View all property information
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    5 of 5 stars Reviewed September 10, 2013
    The Larrier House is a beautifully furnished, comfortable home that has everything we could have possibly wanted in a rental house. The kitchen is incredibly well-appointed...
    5 of 5 stars Reviewed June 1, 2012
    Loved the property and absolutely enjoyed my stay at Larrier House. The house is warm and inviting! The kitchen, living areas and the bedrooms are very clean and have a...
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    1 / 15
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This nicely styled cape sits along the shoreline of Lagoon Pond amid nicely landscaped grounds and gardens, and enjoys a variety of water views from both inside and out. The grounds roll right down to the water's edge, as well as the private dock, which has two slips and can accommodate up to a... View all property information
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    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms / 4 Bathrooms / Sleeps 6
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    • Satellite TV
    • Washer
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    • Pets allowed
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    About this property
    Beautiful, newly built 3 bedroom, 3.5 bath home. Close to town, boat and beach. Each bedroom has en suite bath. First floor bedroom is handicap accessible. Lower level has a large family room. Great screened in porch. Nice yard. Quiet area. Additional amenities include: coffee maker, lobster pot,... View all property information
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    5 of 5 stars Reviewed June 24, 2014
    Beautiful new home at top of Centre St in Vineyard Haven w/ space, comfort, and remarkable privacy very close to town. Accessible to all the island has w/ limited eco-footprint...
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    From
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    1 / 24
    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    About this property
    Tucked away on the eighth fairway of Mink Meadows Golf Club, this contemporary enjoys relaxed living both inside and out, with a large deck and patio that connect with all the main living spaces. The Living Room has vaulted ceiling with beams and brick fireplace. The Dining Room has a wall of glass... View all property information
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    1 / 20
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Enjoy relaxed beach living at your doorstep with views of Vineyard Sound in one direction and Lake Tashmoo in the other. The Beach Cottage is one of only a handful of properties that sit along the Herring Creek Road bluff that separates Lake Tashmoo from Vineyard Sound. With decks on both sides of... View all property information
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    1 / 16
    4 Bedrooms / 3 Bathrooms / Sleeps 7
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    About this property
    Tucked away a block off the harbor, on a quiet West Chop side street, this charming cape has been thoughtfully renovated with style and a coastal palette of colors. The main floor in Ship Shape features an open layout with two Living Areas, a Dining Area, and Kitchen with 'L-Shaped' breakfast bar,... View all property information
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    1 / 24
    5 Bedrooms / 3 Bathrooms / Sleeps 8
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    About this property
    This compound sits directly on the beach with Vineyard Sound literally at your door step. One of only a few homes on the thin stretch of barrier beach that separates Lake Tashmoo from the Sound, this deluxe beach house is designed around its panoramic water views, from the Elizabeth Islands to... View all property information
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    1 / 10
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
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    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    This home is within walking distance of some of the finest golf on the island as well as the beach. It is casual, attractive and immaculate. Sliders in the living area look out to the deck with the water in the distance. The surrounding yard is beautifully landscaped. Note: Beach is a 7 minute walk... View all property information
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    1 / 21
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    Situated on secluded Hines Point, this classically appointed home features fine furnishings and antiques on top of a beautiful waterfront setting. Details like a gazebo, pergola, dock and mooring make this a unique offering. NOTE: Non-refundable dog fee of $75, plus $100 security deposit for dog... View all property information
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    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Perched on a waterfront hillside overlooking Lagoon Pond, this sleekly designed cottage dramatically integrates the water views throughout the home. The main floor Great Room is wrapped by three walls of floor-to-ceiling glass windows and doors. The open Living and Dining areas have a modern,... View all property information
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    1 / 28
    8 Bedrooms / 7 Bathrooms / Sleeps 10
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    About this property
    Situated amid expansive, lushly landscaped gardens on West Chop waterfront, this truly impressive home is one of the most desirable locations on the Vineyard, with sweeping water views of Vineyard Sound over to Woods Hole and the Elizabeth Islands. The signifcant home features eight bedrooms with... View all property information
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    1 / 24
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    Sitting atop a rolling hill in exclusive Lower Makonikey, Sea Star enjoys distant water views of Vineyard Sound and easy access to the association's private north shore beaches. The grand shingle-style home has a large farmer's porch and decks on three levels. The entertainment hub of Sea Star is... View all property information
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    1 / 24
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
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    About this property
    This three bedroom two bath condo is just a short walk to association tennis, pool and beach, Tashmoo Amenities include Direct TV DVD set up. There is an open wifi signal in the building. Additional amenities include: dock/boat-slip, coffee maker, bakeware, lobster pot, dishes, swimming pool: yes... View all property information
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    1 / 22
    4 Bedrooms / 4 Bathrooms / Sleeps 10
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    About this property
    Tucked away in the exclusive Lower Makonikey area, this large country Gambrel features stylish detailing throughout, and access to the association's private north shore beaches. The entertainment hub is a large open Living Room with home theater and fireplace, that connects to an equally large... View all property information
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    1 / 27
    4 Bedrooms / 5 Bathrooms / Sleeps 8
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    About this property
    With sweeping views of Vineyard Haven Harbor, this newly built in-town luxury home combines commanding water views with four levels of sophisticated and stylish living space, including two roof top decks, Home Theater, tournament pool room, penthouse lounge, and more. The main floor of Hill House... View all property information
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    1 / 21
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
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    About this property
    This classic West Chop cottage combines stylish detailing with water views of Vineyard Haven Harbor, and access to one of Chilmark's most prestigious private beaches The first floor features sunny living and entertaining areas, with wide plank pine floors and lots of windows. Formal Living Room has... View all property information
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    5 Bedrooms / 3 Bathrooms / Sleeps 9
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    About this property
    Tucked away on a quieter side street, this in-town historic home has been recently renovated with thoughtful touches throughout. The large, heated pool enjoys its own private backyard location, set amid the property's nicely landscaped grounds, perennial gardens, and old growth trees. The... View all property information
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    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Suitable for children
    • x
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    About this property
    Step into yesteryear in this beautifully maintained, comfortable home. This recently renovated Island classic has spacious rooms, a wonderful front porch and overlooks the historic Vineyard Haven harbor in the distance. You can also sit in the Queen Anne recliner in the front bedroom and enjoy the... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    About this property
    True beachfront ocean living on a barrier beach bluff with panoramic water views of Vineyard Sound in one direction, and Lake Tashmoo in the other. Designed to take advantage of these stunning east/west views, the Bungalow Cottage Compound features a two-bedroom Main Cottage and a separate... View all property information
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    6 Bedrooms / 4 Bathrooms / Sleeps 11
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    • Elder access
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    About this property
    This historic colonial sits atop the West Chop bluff and enjoys sweeping water views of Vineyard Haven Harbor across to the East Chop Lighthouse and out to Vineyard Sound. Built as a tavern in the mid 1700's, this vintage property has been lovingly transformed into a family-friendly West Chop... View all property information
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    4 Bedrooms / 5 Bathrooms / Sleeps 8
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    About this property
    This stunning architect-designed waterfront home sits majestically atop a high bluff in West Chop, overlooking Nantucket Sound with sweeping water views. The Bluff House compound also features a Guest House, private sandy beach and deep water dock. Designed to dramatically maximize water views by... View all property information
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    About this property
    This magical waterfront cottage has just been renovated from top-to-bottom for the summer, with new modern, cottage-styling throughout its new Living/Dining Area, Kitchen, and Bedroom. Air conditioning has been added, as well as new furniture, floors, paint, and outdoor shower. The cottage sits... View all property information
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    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
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    About this property
    Delightful three bedroom, 2 bath home in a quiet location. Amenities and Features include... West Chop Area, Wifi, A/C Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd player, landscaped, outside shower - enclosed, pets... View all property information
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    5 of 5 stars Reviewed August 8, 2014
    Not exactly in the woods, but secluded enough that it feels that way. We have been coming for years, and each year it gets better. Recent improvements include a new kitchen and...
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    4 of 5 stars (1) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • x
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    About this property
    Spacious contemporary townhouse with expansive deck, cathedral ceilings, open floor plan, central air conditioning and gas grill. Upper level has 2 bedrooms with Queen beds and 2 bathrooms. Main level has living with 2 story cathedral ceilings, dining area with window seats, eat-in kitchen and den.... View all property information
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    4 of 5 stars (1) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Dishwasher
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    • Satellite TV
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    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
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    About this property
    This cottage,designed by Island architect Jamie Weisman faces West (great sunsets!)and has expansive views of the water from the Adirondak chairs on the white sandy beach. Imagine waking up and looking out at the water with its attending wildlife, or ending your day with your favorite beverage... View all property information
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    $1,800
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    4 Bedrooms / 2 Bathrooms / Sleeps 9
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    This charming Vineyard house at the end of a mile long dirt road with waterviews with a private beach a few steps from the door has among the best views on the Island. Ideal Vineyard atmosphere with an up-Island feel and down-Island convenience. Spectacular views of Tashmoo Inlet and Vineyard Sound... View all property information
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    $5,950
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    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Satellite TV
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    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Located on the beach with spectacular views of the Vineyard Sound, Elizabeth Islands and glorious sunsets. Across the road is Lake Tashmoo with its fabulous clamming. This light and bright cottage is decorated with comfortable and attractive contemporary furnishings. Fabulously located on a barrier... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    About this property
    VINEYARD HAVEN EXCLUSIVE Tucked away from all the hustle and bustle of summer on the island and still only a mile from the center of town. House is as pristine as the pictures show. Bright, airy and open living, kitchen and dining area. Sliders open from the dining area to the completely enclosed... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Satellite TV
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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
    The Hideaway, New Wing, has about 2500 sq. ft living area, with three stories. It has four bedrooms, three baths. The New Wing, is stepped 4 ft up from the rest of the house, and made private with plantings and fencing. On the South side of the house, is a secluded garden area with outdoor dining... View all property information
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    4 Bedrooms / 5 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    A Beautifully designed and decorated comfortable home just one mile from downtown Vineyard Haven. Sweeping water views for the Master bedroom will have you entranced. The summer breezes provide a cooling caress. The many amenites offer solace during your much needed vacation. Come and play or just... View all property information
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    3 Bedrooms / 1 Bathroom / Sleeps 6
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    • Dryer
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    • Satellite TV
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    • Waterfront
    • Water Views
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Fabulously located on a barrier beach with ocean in the front and a saltwater pond in the back. Traditional beach cottage features a bedroom right on the ocean side and a separate studio for kids or guests. Located ON THE SOUND the sunsets are astounding--the views over Lake Tashmoo are exquisite.... View all property information
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    $4,415
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    7 Bedrooms / 6 Bathrooms / Sleeps 18
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
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    • Suitable for children
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    • x
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    About this property
    Beautiful Vineyard home and guest cottage located in the Mink Meadows community of West Chop. This home offers and in-ground swimming pool and lovely yard and deck for relaxing and outdoor dining. The main house has three bedrooms on the 2nd floor with a master en suite bedroom/bathroom. The first... View all property information
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    4 of 5 stars (1) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 6
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    • 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
    MVVR EXCLUSIVE: Serene setting looking out on green grassy meadow, offers complete privacy and peaceful surroundings yet is only 2 1/2 miles from the nearest beach and 4 miles to town. Property abuts reservation land offering miles of trails. Amenities and Features include... Lambert's Cove,... View all property information
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    4 of 5 stars Reviewed August 26, 2014
    This home is extremely secluded - a rustic log cabin sort of home, a dirt road leads you to the home and you have complete privacy. One caution is that ticks are rampant on the...
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