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5 BR / 1 BA / Sleeps 8

19 Mill Square Road - Oak Bluffs vacation rentals
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19 Mill Square Road

5 BR / 1 BA / Sleeps 8 | Quick view

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Beautiful Vintage East Chop water view cottage offering panoramic views from the porch, most windows and bedrooms. This lovely East Chop home has 5 bedrooms and ample living space for your family to enjoy and make their own. There is a large lawn for games and leisure and the outdoor shower is sure to please. Less …
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4 BR / 3 BA / Sleeps 12

38 Farm Pond Road - Oak Bluffs vacation rentals
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38 Farm Pond Road

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Quintessential Vineyard House and Guest House in prestigious Harthaven neighborhood on Farm Pond. Three large bedrooms and two full baths in 'Frank Lloyd Wright' style main house with huge deck, outdoor shower, cable TV/VCR/DVD, and A/C. Additional huge bedroom, full bath and kitchen in large Guest House accessible …
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3 BR / 3 BA / Sleeps 8

45 Bridle Path Road - Oak Bluffs vacation rentals
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45 Bridle Path Road

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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 comfortable furnishings…
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4 BR / 2 BA / Sleeps 8

23 Green Avenue - Oak Bluffs vacation rentals
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23 Green Avenue

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Gorgeous East Chop.Luxury+ location= Vineyard Ideal.This beautiful East Chop home is for the guest who expects only the best the Vineyard has to offer. Head out in any direction and quickly find beach, tennis, lighthouse, water, town, all walking distance.The gourmet kitchen has every amenity and the adjoining family/…
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3 BR / 2 BA / Sleeps 6

42 Waterview Road - Oak Bluffs vacation rentals
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42 Waterview Road

3 BR / 2 BA / Sleeps 6 | Quick view

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Waterview Farm is a private association with wonderful meadow and water views.  It is adjacent to Farm Neck Golf Club, which is open to the public. There is access to Sengekontacket Pond to launch a canoe or kayak from the private association beach.  This is also a great spot for children to swim, play and picnic…
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3 BR / 2 BA / Sleeps 9

135 New York Avenue - Oak Bluffs vacation rentals
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135 New York Avenue

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Tucked behind a beautiful hedgerow, this restored bungalow is just up the hill from Oak Bluffs center and on the outskirts of East Chop. Comfortable and loaded with personality, the large living room opens to a breezy sleeping porch. A simple yet well-stocked kitchen is graced by a lovely dining room. Three unique …
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4 BR / 4 BA / Sleeps 7

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9 Mourning Dove Way

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Quiet and quaint, this home sits on a beautifully landscaped yard and overlooks a freshwater pond. Sleeps 7 with 3 bedrooms in the main house and one guest room over the garage, with it's own private bathroom. Gorgeous in-ground pool in back of the main house. Newly added central air conditioning! Additional …
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4 BR / 2 BA / Sleeps 8

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49 Tuckernuck Avenue

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Cute cottage located walking distance to Circuit Avenue and the beach. No need to bring you car, restaurants, bars, grocery store all are walking distance from this home.Four bedroom, two bath home with all the amenities you will need on your vacation. Across the street is a park for the kids, public tennis courts and…
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6 BR / 4 BA / Sleeps 12

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25 Farm Pond Road

6 BR / 4 BA / Sleeps 12 | Quick view

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Situated on Farm Pond with views of the pond and Nantucket Sound is this charming summer house and guest cottage. Homes have antique charm with modern amenities. Located in Harthaven, you will have use of the neighborhood's private beaches and tennis. The main house has 4 bedrooms and 2.5 baths plus a shower room and …
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3 BR / 2 BA / Sleeps 8

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31 Hidden Cove Road

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Three story 1980's contemporary home in the well maintained Hidden Cove development. Three miles from Oak Bluffs State Beach or the Edgartown Harbor. Access to two association tennis courts in the development as well as a boat launch area (kayaks, canoes). Two bedrooms and one full bathroom on the 1st floor. Half bath…
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5 BR / 4 BA / Sleeps 9

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114 Park Street

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Home is located a very quiet section of the East Chop Area of Martha's Vineyard. The lower level of the house has a complete mother-in-law apartment with ground level entrance. The home is spacious with 3 bedrooms on the top level & 2 bedrooms in the lower level. Each bedroom, and the over sized 2 level deck, …
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4 BR / 2 BA / Sleeps 8

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2 Quail Run

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This large, natural-shingled home in the pines of Sengekontacket redefines the "rambling Cape." Built in 1984, the home is spacious and includes four bedrooms, two and a half baths, a formal living room and a casual family room. Association pond and tennis available. Additional amenities include: bakeware, coffee …
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5 BR / 2 BA / Sleeps 10

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125 Munroe Ave

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OAK BLUFFS EAST CHOP: Classic turn-of-the century shingle style seasonal residence exudes the character and charm of the era is situated just a block from the East Chop Bluffs on a sleepy side street in a quiet wooded setting. There is a large bright kitchen that accesses a separate dining room with brick fireplace, …
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4 BR / 3 BA / Sleeps 8

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32 Waterview Farm

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This beautifully renovated farmhouse is located in the desirable Waterview Farm neighborhood next to the third fairway of Farm Neck Golf Course and has lovely second floor views of Sengekontacket and the barrier beach. Bright, open floor plan with first and second floor master suites and a wall of glass overlooking …
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5 BR / 3 BA / Sleeps 9

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19 Farm Pond Road

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Relax and enjoy your summer vacation at this great home on Farm Pond in Oak Bluffs. Owned by the same family since 1932, this property defines authentic Vineyard charm! The house is on one level, with the master on one side and three bedrooms at the other end of the house. In between is a large living room with …
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73 Park Street

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Waterfront custom Cape overlooking Crystal Lake towards East Chop Drive. There is a large manicured lawn and garden with a path to the lake and a row boat for your enjoyment. Sit on the large deck with an 8'x15' hot tub/ dip pool, outdoor shower and enjoy the view, or grill on your brick water-view patio. A very …
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4 BR / 3 BA / Sleeps 8

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38 Waterview Farm Road

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This bright airy contemporary has wonderful views to the east and south over Sengekontacket Pond to Cape Pogue, with amazing sunrises.  To the west, enjoy the ever changing vistas of a 12 acre rolling meadow.  The walls of glass and interesting angles create a unique and inviting interior, with cathedral ceilings, …
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6 Fresh Pond Road

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This spacious 3,000 sq.ft. home has four bedrooms and three and half bathrooms.  Set on 1.5 acres with views of the pond.  Central air conditioning and wireless internet are provided. The main floor has a separate living room as well as family room.  The kitchen is fully equipped and has stainless steel appliances …
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4 BR / 1 BA / Sleeps 6

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91 Meadow Avenue

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Tucked in a quiet neighborhood and within walking distance to town and beaches, this quaint cottage was moved to East Chop from the campgrounds at the turn of the century.  This simple yet charming and well-equipped bungalow has been in the same family for many years and is a lovely place for a vacation. Come relax …
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3 BR / 2 BA / Sleeps 6

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14 West Meadow Lane

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This 3 bedroom, two and ahalf bath Cape Style home is located in a wonderful neighborhood situated closeto the bike path leading to downtown Oak Bluffs. This beautiful sunny interiorhas lots of glass and lovely appointments. The home features include, a first floor master bedroom with a private bath and a large …
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6 Linden Avenue

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Beautiful three bedroom two and a half bath home located in Oak Bluffs. Walking distance from the lagoon and beach. Close proximity to downtown Oak Bluffs and the beaches. Large backyard and deck and finished basement. Queen sofa bed in basement. Additional amenities include: beach chairs, sofabed, bakeware, coffee …
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6 Anthier's Lane

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This brand new builder's home is located in the desirable Farm Neck Association and has lovely views over Sengekontacket Pond. Enjoy easy access to golf, tennis, beaches, bike path and downtown Oak Bluffs and Edgartown. The interior is casually elegant, comfortable for families and entertaining with five bedrooms, a …
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2 BR / 2 BA / Sleeps 6

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273 Barnes Road

2 BR / 2 BA / Sleeps 6 | Quick view

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This expansive, single-level waterfront home sits on a one-acre, wooded lot with a private beach. Enjoy panoramic views of the Lagoon and beyond. The home features a large living room with water views, a den with a queen sofa bed, and a screened porch off the den. The kitchen has new cabinets and an adjoining laundry …
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4 BR / 2 BA / Sleeps 8

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10 Tamarack Lane

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Perfect location for golfers near hole #8 on Farm Neck Golf Course! This home offers four bedrooms and two and a half bathrooms.  Spectacular water views over Sengenkontacket and ocean and much more! Close drive or bike ride to State Beach. Enjoy your stay on the Vineyard with comfort and style.
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