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Holiday Rentals and Homes in Oak Bluffs, MA

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    280 Holiday Rentals in Oak Bluffs
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    €2,314
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    1 / 17
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    €5,277
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    About this property
    Watch the boats come and go from the harbor while you picnic and relax on your beach. This fabulous waterfront three bedroom main house and three bedroom guest house also offers your own dock and mooring. Additional amenities include: beach chairs, dock/boat-slip, coffee maker, bakeware, outdoor... View all property information
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    Stylish Cape located close to town and beach.attention to detail in every room. Relax and enjoy all the comforts of home in this all new pristine 3 bedroom, 2 bath home. The main living level features an open kitchen living and dining with AC. In additon there is separate TV room with office area... View all property information
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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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    Little Jaws, the home where the movie Jaws was filmed is a pristine beach cottage. Set in East Chop, this three plus bedroom rental offering features spectacular views, great swimming, kayaking and gorgeous sunsets. Relax on the large and comfortably furnished waterfront veranda. The living room... View all property information
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    8 Bedrooms, 3 Bathrooms, Sleeps 16 | Quick View
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    About this property
    A large and quiet property in East Chop. This beach home sleeps 16 and includes 8 bedrooms, 3 baths, as well as a large enclosed outdoor shower. The house is located 400 feet from the local jetty beach and yacht club and only a 10 minute walk around the harbor into Oak Bluffs. Although carefully... View all property information
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    €1,528
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    A charming early 1900s cottage in Oak Bluffs, just completely renovated. Walk to town, park, beach and steps to library. Two bedroom, one very large full bathroom. Spacious working, eat-in-kitchen with all stainless steel appliances and washer/dryer. Separate dining area. Cable, TV, Wi-fi, Ipod... View all property information
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    This beautiful fully renovated cottage beach house is available for weekly rent. Come enjoy the great ocean views. Sit out on the large front covered porch – enjoy friends, family and great times! Relax to the sights and sounds of the beautiful ocean. House comfortably sleeps 10 and includes a... View all property information
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    About this property
    Bright and newly remodeled classic summer cottage. Conveniently located just one mile from Oak Bluffs town center, Ink Well Beach, shops, fine and family dining, historic Flying Horses Carousel, public tennis courts, Bandstand Park and Oak Bluffs Harbor-front area. The professionally landscaped... View all property information
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    About this property
    Wonderful four bedroom, two bath home completely redecorated. Features wrap around porch, living room and sun porch/TV room. Amenities and Features include... Classic Oak Bluffs Summer Home, Walk to Town and Beach, On Street Parking Additional amenities include: coffee maker, patio table and... View all property information
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    3 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    About this property
    Come and enjoy this relaxing home near Sengenkontacket Pond, in the Waterview Farms neighborhood.  Beautiful distant views from the large second floor deck, out to Sengekontacket pond and the ocean.  Association includes small sandy beach and shared use of dock on the pond, as well as acres of... View all property information
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    1 / 36
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Close to everything, yet far from the crowds.This cozy campground Victorian is on a quiet street between two parks in East Chop. The three bedroom, one and a half bath cottage, comfortably sleeps six. The sunny light filled rooms, exposed rafters and painted white walls, exude an atmosphere of... View all property information
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    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,... View all property information
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    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Recently renovated. New bathrooms. Air-conditioned. Fantastic location. All the charm of OB in an updated, clean and comfortable home. This house is perfect for families with children. The neighborhood is quiet and relaxing but all of the action is just a stroll away. Ocean Park, the beach and... View all property information
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    About this property
    Adorable Beach Chic Cottage and oh so nicely decorated. Walk to Town Center, Harborfront, Parks and Inkwell Beach. Amenities and Features include... Walk to Town and Beach, Wifi Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer /... View all property information
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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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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    OAK BLUFFS: The Highlands. Less than one mile to town. Immaculate, comfortable and family friendly.First floor; living room, dining area, kitchen, queen bedroomm twin bedroom and bath. Second floor has twin bedroom and full bedroom and a second bath. DSL internet connection. Departure cleaning... View all property information
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    About this property
    Outrageous views from this third floor condo #304) overlooking the beach in Oak Bluffs. Walk to Circuit Avenue for all the happenings in town. Well equipped and nicely decorated, this is a great get-away venue. Elevator, parking, convenience. Additional amenities include: beach chairs, sofabed,... View all property information
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    €1,690
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    Amenities and Features include... Hidden Cove, Centrally Located to Beaches and Towns, Association Tennis Courts, A/C, WiFi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, landscaped, outside shower - enclosed, vacuum, phone ld... View all property information
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    5 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Penacook 5 Bedroom Cottage - short stroll down one of the nicest streets in Oak Bluffs to the beach and town. Completely, refurbished and all new appliances, furnishings, and bedding. Great backyard patio and grill area. Amenities and Features include... In Town, Walk to Beach Additional... View all property information
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    Amenities and Features include... Hidden Cove, Association Tennis Courts, Association Kayak Landing Additional amenities include: coffee maker, fans - portable, lobster pot, food processor, washer / dryer, porch - screened, vacuum, outdoor furniture, tennis - association/shared, ironing board. View all property information
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This beautiful Victorian cottage is just half a block to the Inkwell Beach and only a short walk to downtown Oak Bluffs. Relax on the covered porch and enjoy views of Vineyard Sound and the  lively atmosphere of the town, or retreat to the private patio and garden tucked behind the house.  The... View all property information
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Perfect location for golfers near hole #8 on Farm Neck Golf Course! This home offers four bedrooms and two and a half bathrooms. A  spectacular water views over Sengenkontacket and ocean and much more! Close drive or bike ride to State Beach as well as downtown Oak Bluffs. Enjoy your stay on the... View all property information
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    About this property
    East Chop Victorian home. Newly renovated in 2011. Walk to the Bluff and enjoy panoramic ocean views. Bike to the public beach by the beach club or into town and the large public beach beyond. Large flat screen TV in living area and wireless internet for your convenience. There is also a smaller TV... View all property information
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    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... View all property information
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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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... View all property information
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    4 Bedrooms, 4 Bathrooms, Sleeps 7 | Quick View
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    About this property
    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!... View all property information
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    6 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    About this property
    Newer home built in 2008 with 6 bedrooms, 6.5 baths located in Hart Haven in Oak Bluffs, off of Beach Road. Two private association beaches, one with raft perfect for children. Private harbor and association tennis court.Home overlooks Farm Neck golf course and has large deck, central air... View all property information
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    Custom Crafted Luxury Home on Farm Neck Golf Course This gorgeous 5 bedroom home overlooks the golf course and Sengekontacket Pond. Large family living spaces include a great room with soaring ceilings opening to the patio as well as a large TV/family room. The expansive kitchen is custom designed... View all property information
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    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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    Cozy guest house sleeps 4. Open floor plan with queen bed alcove off of living room. One bedroom with one set of bunk beds. Large deck with view of Lagoon. Owner or guests occupy main house. Amenities and Features include... Lagoon Guest House, Walk to Private Lagoon Beach Additional amenities... View all property information
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    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Large Victorian, beautifully furnished in wicker, wood, withdesigner  accessories, stone fireplace,stained glass windows, large wrap around porch (fully furnished) , fenced in yard with extensive landscaping. This magnificent home is bright and airy, wood floors, freshly painted. Five large... View all property information
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    This Circa 1910 Cottage has been completely renovated and is fresh and light, bright and cheerful, welcoming and an absolute delight. It is within walking distance of the ferry, town center, the active harbor, public beaches and just steps away from the library. Very central but in a sweet,... View all property information
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Spacious 4 bedroom, 4 bath home set in a lovely and quiet neighborhood. All modern amenities provided. Amenities and Features include... Walk to Town and Beach, Wifi Internet Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, cd... View all property information
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    €1,273
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Lovely cape home, all newly refurnished for 2013. First level features an open floor plan in the Dining, Kitchen and Living area. The tastefully decorated living area features comfortable furnishings and a 36' screen tv. One bedroom with a double bed and a full bath complete the living level. 2nd... View all property information
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    €1,250
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    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Amenities and Features include... Waterfront, Waterview, Wifi Additional amenities include: coffee maker, patio table and chairs, fans - portable, lobster pot, washer / dryer, outside shower - enclosed, outdoor furniture. View all property information
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    From
    €8,170
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This home offers a spacious open floor plan providing a comfortable yet elegant retreat, truly an upscale surprise, perfect for relaxing or entertaining. With an expansive mahogany wraparound deck, sweeping views and a screened-in porch, enjoying the evening sunsets while grilling and dining al... View all property information
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    From
    €2,245
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    • Dishwasher
    • Grill
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Amenities and Features include... Meadow View Farms, Out of Town, Association Tennis, Hi Speed Internet Additional amenities include: coffee maker, internet - ethernet cord required, fans - portable, lobster pot, food processor, washer / dryer, cd player, landscaped, patio table and chairs,... View all property information
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    From
    €2,129
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    • Dishwasher
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    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Surrounded by a green part shade, part sunny yard with a patio deck for basking in the sun or grilling outdoor dinners, this house is located on New York Ave half a mile from the beach. A lovely sleeping porch adds room for more in this colorful and welcoming home. An informal dining room and a... View all property information
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    From
    €2,407
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    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Spacious and attractive waterfront Cape Cod style home - features gorgeous views, central A/C, Wi-Fi and 4 TV's. Two large decks and a screened porch provide wonderful spaces for summer relaxation in which to enjoy the waterviews. Kayaking enthusiasts will enjoy the gorgeous scenery and wild life... View all property information
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    From
    €2,777
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    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    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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    From
    €7,499
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Beautiful luxury home overlooking Farm Neck Golf Course and Sengekontacket Pond. Large family living spaces include a great room with soaring ceilings opening to the patio as well as a large TV/family room. Expansive gourmet kitchen with dining area is great for family gatherings after the beach.... View all property information
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    €1,805
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    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    East Chop - 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 the... View all property information
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    From
    €4,629
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
    Overview
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    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... View all property information
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    €5,092
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    Overview
    Amenities & Details
    • Dishwasher
    • Grill
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Large families looking for a beachfront adventure will love this relaxed waterfront home. Spectacular views from every room and expansive patios stretch the shoreline. Central location offers a 5 minute drive to town, dining, movies, shops and galleries. Amenities and Features include...... View all property information
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