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Holiday Homes and Apartments Oak Bluffs, MA

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    All 353 Rentals in Oak Bluffs
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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
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    $2,803
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    1 / 17
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    $1,529
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    5 Bedrooms / 2 Bathrooms / Sleeps 10
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    3 Bedrooms / Sleeps 8
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    About this property
    Quaint family cottage on Vineyard Haven Harbor, with great ocean views. Private beach, dock and mooring. Adequate parking, including area for a boat trailer. beautiful sunsets, ideal for a family vacation. Additional amenities include: beach chairs, dock/boat-slip, beach cooler, which beach:... View all property information
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    1 / 10
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    About this property
    This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The... View all property information
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    1 / 14
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    The Blue Canoe is a bright, welcoming vintage 1900 s cottage with enormous charm and style. Freshly renovated, and decorated with an eye to capturing the casual and colorful feel of an island retreat. Ideally located on a quiet street, within walking distance of the village, the beach and parks. A... View all property information
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    1 / 14
    5 Bedrooms / 4 Bathrooms / Sleeps 13
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    • Air Conditioning
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    • x
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    About this property
    This newly renovated Oak Bluffs home offers a spacious interior, with plenty of nooks for all to have their own space. A spacious deck and yard are perfect for entertaining and cookouts. The attic offers a wide open floor plan which is perfect for kids to get away from mom and dad. This home offers... View all property information
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    1 / 14
    4 Bedrooms / Sleeps 8
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    • Internet Access
    • Satellite TV
    • Water Views
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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
    Contemporary Cape on Martha's Vineyard. Open design, wood floors downstairs. Deck for extended summer living. Distance waterview of the Lagoon from outside deck. Short distance to Oak Bluffs center. Additional amenities include: outdoor shower: enclosed, square ft.: 1916, house style: contemporary... View all property information
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    1 / 25
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Satellite TV
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    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    About this property
    Classic vineyard home with a beautiful covered front porch and two car garage. Located in a peaceful, quiet neighborhood. Nicely maintained gardens and lawn, great for relaxing and enjoying the outdoors. Newly furnished throughout, comfortable and fresh interior. Modern conveniences of wireless,... View all property information
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    1 / 12
    4 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Charming cottage located in East Chop, a short walk to Sunset Lake and Oak Bluffs Harbor. Recently renovated, with hardwood floors and a nice wrap around deck. Comfortable, family friendly, well equipped home with DSL connection. Ideally located, within walking distance to downtown Oak Bluffs,... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    This charming Cape style Oak house residence is situated on a wooded lot near bike path and just a short ride to town center and ferry. This home features an open design with a bright kitchen/dining/living area with hardwood floors, den and full bath on the first floor. Sliders in the dining area... View all property information
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    1 / 7
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Amenities and Features include... Walk to Town and Beach, Newly Renovated Additional amenities include: coffee maker, patio table and chairs, lobster pot, washer / dryer, landscaped, outdoor furniture, ironing board. View all property information
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    1 / 12
    4 Bedrooms / 2 Bathrooms / Sleeps 7
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    • x
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    About this property
    Charming Gingerbread Cottage located in the Tabernacle area of Oak Bluffs. A short stroll brings you to Oak Bluffs Center with shops, family and fine dining, harbor area, bandstand park, and Ink Well Beach. Recently updated, this house features a modern eat in kitchen opening to the back deck and... View all property information
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    1 / 12
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Waterfront
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    About this property
    This well appointed larger corner unit faces the Inkwell Beach and historic Waban Park. Spacious living with two bedroom, and two baths. A short walk to Circuit Ave, and the Oak Bluffs Harbor. Additional amenities include: sofabed, coffee maker, smoke free, pet free, 4 dining capacity, lobster... View all property information
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    1 / 24
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    About this property
    Enjoy the magnificent views of Nantucket sound from the three season room and multiple decks. Spacious four bedroom three bath home located in East Chop. Only a 1/4 mile from the center of Oak Bluffs and the public beach. Additional amenities include: coffee maker, smoke free, lobster pot, 2 king... View all property information
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    1 / 25
    6 Bedrooms / 5 Bathrooms / Sleeps 12
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    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
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    About this property
    Beautiful Vineyard home overlooking the ocean on Farm Neck Golf Course. Five bedroom, four baths, open living area with screened in porch, large wrap-around deck. Also small guest apartment over the garage with one bedroom, bath and living room. Tennis and golf on the grounds, public beach nearby.... View all property information
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    1 / 12
    3 Bedrooms / Sleeps 6
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    • Air Conditioning
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    • Fireplace
    • Grill
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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
    You are just minutes away and within walking distance to the hustle bustle of the charming, colorful and historical harbor village of Oak Bluffs where you will find the oldest carousal in the country, fireworks in August, concerts on the green and a wide variety of restaurants, shops and beaches to... View all property information
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    1 / 30
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    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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    $1,816
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    1 / 12
    3 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
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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: Adorable pristine beach cottage has spectacular views across the sound, calm water swimming, great area for kayaking. The opening kitchen, dining and living areas are enhanced by the wall of windows faciing the waterfront and providing gorgeous water views . Enjoy the parade of... View all property information
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    $3,536
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    1 / 10
    4 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Private Outdoor...
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    • Pets allowed
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    • x
    • x
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    About this property
    Amenities and Features include... Private Pool, High 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, outside shower - enclosed, phone ld... View all property information
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    From
    $2,166
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    1 / 11
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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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
    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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    1 / 13
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    About this property
    Beachfront living combined with the convenenience of in-town. This condo makes your Vineyard vacation easy. Enjoy sweeping ocean views of Nantucket Sound and Chappaquiddick, with Oak Bluffs' popular Inkwell Beach directly across the street. Enjoy a second floor condo with water views from the... View all property information
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    1 / 15
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    • Suitable for children
    • ?
    • x
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    About this property
    Great three bedroom, 1.5 bath summer cottage in Waterview Farms. Lots of light throughout with a large deck that overlooks common ground meadow. Additional sleeping in loft area. Nice location to town and beaches. Additional amenities include: coffee maker, smoke free, loft, 1st floor bedroom, 2... View all property information
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    1 / 13
    3 Bedrooms / 2 Bathrooms / Sleeps 7
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    • x
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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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    1 / 6
    4 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Dishwasher
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    • Suitable for children
    • x
    • x
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    About this property
    Close to everything, Town, Beach, Tony's Market, etc! Main house has 4 Bedrooms plus a den with two daybeds. Guest house has an upstairs bedroom with queen bed and a sleeper couch in living room. There is no door to the upstairs bedroom, but there is a reasonable amount of privacy between the two... View all property information
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    2 Bedrooms / 1 Bathroom / Sleeps 5
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    • Suitable for children
    • x
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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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    4 Bedrooms / Sleeps 8
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    About this property
    Four Bedroom multi level home in Water View Farms. Short distance to Farm Neck golf course. bike path and Oak Bluffs center and beach. Rental comes with an Association beach access on Sengekontacket Pond as well as association floating dock for small watercraft. Great house for 2 couples plus... View all property information
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Suitable for children
    • x
    • x
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    • x
    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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    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • x
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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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    1 / 14
    4 Bedrooms / Sleeps 7
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    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • ?
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    About this property
    Easy breezy summer living in this fresh and airy cape. With new paint and furniture this house has many different areas for everyone to enjoy. An eat in kitchen offers easy entertaining. Leading to a family room with cozy couches and a new flat screen tv. With an association tennis court and... View all property information
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Suitable for children
    • x
    • x
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    About this property
    View of Sunset Lake and distant views of Oak Bluffs harbor are at this 4 bedroom, 3.5 bath home. The first floor has a great, living, dining and kitchen area and den which offer a private staircase to the “Honeymoon” suite with private bath. Back in the living room you can enter a separate... View all property information
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    1 / 17
    6 Bedrooms / Sleeps 16
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    • x
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    About this property
    Contemporary home sits on 1.4 acres. Three master suites two with Jacuzzi's. Fully equipped eat-in kitchen. Sunroom with sunken hot tub along with another hot tub outside. Large brick patio, complete with outdoor furniture and built-in stone BBQ pit. All bedrooms are equipped with window air... View all property information
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    1 / 15
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Suitable for children
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    About this property
    Enjoy beautiful waterviews of Farm Pond and Nantucket Sound while relaxing on the back deck. This vintage Vineyard Cottage located in the private Harthaven association has access to 2 private association beaches as well as a private tennis court. Additional amenities include: games, coffee maker,... View all property information
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    1 / 9
    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    About this property
    Sunny contemporary, newly furnished home located in a beautifully landscaped association. Providing tennis courts and a kayak landing on Sengenkentac. With a screened in porch and deck there is plenty of space for outdoor living. Centrally located only a short drive to downtown Oak Bluffs,... View all property information
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    $3,345
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    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Grill
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    • Waterfront
    • Water Views
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    • Pets allowed
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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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    5 Bedrooms / 2 Bathrooms / Sleeps 11
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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
    Privately situated on a hilltop in Sengkontacket, -spacious tri-level contemporary home. This wonderful vacation home has been updated for summer 2015, AC added, freshly painted, new carpeting and hardwood flooring and new furnishings. Set in a wonderful family friendly community offering... View all property information
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    $3,441
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    3 Bedrooms / 1 Bathroom / Sleeps 7
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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
    Classic vineyard cottage renovated, tastefully and comfortably furnished. Large open deck on both the main and 2nd levels. Main living level features a lovely kithcen very well stocked with dining and cook items, a large sunporch living area and 2nd aliving area with large screen TV. Three lovely... View all property information
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    3 Bedrooms / Sleeps 6
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    Amenities & Details
    • Dishwasher
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Spacious 2 bedroom in Oak Bluffs. Open, airy Cape. Walking distance to Circuit Avenue, Oak Bluffs Town Beach, library and playground. Open floor plan has large living/dining/kitchen area on first floor, along with 2 bedrooms and both full bathrooms. Upstairs is one huge room with 2 twin beds and a... View all property information
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    $2,854
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    3 Bedrooms / 2 Bathrooms / Sleeps 7
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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
    Owner Transfer Ferry Tickets - Please Inquire Situated on quiet side street with a 15 minute walk or a 5 minute drive to town and beach, this light filled cape offers visiting families a well equipped vacation reprieve with comfortable living areas, modern kitchen, AC in all bedrooms. The first... View all property information
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    $2,071
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    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    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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    $3,186
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This home is Oak Bluffs at its best - close to town but tucked away off a main street, the house is truly a beauty with special, thoughtful details and wonderful furnishings. The new home has the yummiest colors with a handsome, soft blue master bedroom and bath, a twin bedroom in warm gold, one... View all property information
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    $1,911
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy the charm of a Vineyard cottage with all the amenities of today. This 3 bedroom house has brand new furnishings for 2015. It is in a quiet neighborhood not far from Oak Bluffs center and its harbor. The house is also close to the bike path. The house has an open floor plan with a large... View all property information
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    $6,371
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    5 Bedrooms / Sleeps 10
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Ideal Oak Bluffs location...This charming Victorian gingerbread beach house with its fabulous verandah has plenty of comfy outdoor furniture and a porch swing to accommodate any ones conversation and relaxation. The best feature of this rental property is that you are only one block away to Inkwell... View all property information
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    $7,009
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    4 Bedrooms / Sleeps 11
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    2012 total renovation, luxurious waterfront 4 bedroom all private bathrooms, fully air conditioned, by their own individual high efficiency mini-split units, beach house with state of the art kitchen, gorgeous and comfortable furnishings throughout, fabulous decking to outdoor entertaining... View all property information
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    $3,536
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Owner Transfer Ferry Tickets Included in Rate for Available July Weeks - Please Inquire Beautiful, spacious, 4 bedroom 3.5 bath contemporary home set in a quiet lovely community on the outskirts of Oak Bluffs. This home comfortably hosts extended families with multiple living spaces. The main... View all property information
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    $2,485
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    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    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
    $4,779
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    6 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Seaside Cottage Style Vacation Home. Recently renovated. Perfect for extended families. Walk to Oak Bluffs town center, beach across the street and miles of beach side - bike paths begin just a couple of hundred yards from the house. Ocean views from just about all rooms. Wonderful, large summer... View all property information
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    $7,009
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    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Set in a quiet section of Meadow View Farms, this contemporary farmhouse is nicely styled throughout and conveniently located between Oak Bluffs and Vineyard Haven. The first floor features a large Living Room with vaulted ceiling, fireplace, media center, and sliding doors to the back deck and... View all property information
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    From
    $3,090
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    4 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Satellite TV
    Suitability
    • 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
    $3,823
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    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    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
    MVVR EXCLUSIVE: Custom crafted tri-level, this beautiful home features spacious open living spaces, hardwood floors throughout, 3 full baths, central A/C and WiFi. Exterior features include a large private deck at the back of the house, the perfect venue for summer dining or just relaxing with a... View all property information
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