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Oak Bluffs Holiday Homes

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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    All 233 Rentals in Oak Bluffs
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    Charming 3br Getaway in Oak Bluffs1 / 22
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oak Bluffs Contemporary Summer Home1 / 18
    (8)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Oak Bluffs Rental - Walk to the Beach1 / 27
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    Welcome to Martha's Vineyard all people, local/foreign/happy/LGBT/Spiritual-not! Our home is located across from Norton's Farm and public transportation. Car and motorbike are best to access everything from this location. The twin room contains two single beds, great for teens, traveling...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Charming house with lots of entertainment and gourmet kitchen!1 / 24
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2018
    The house was clean and centrally located. It was decorated with updated decor. The setting was quiet. It was perfect for our family.
    Reviewed 11 October 2017
    Everyone who stayed here loved the place. We were down for a wedding and pretty much just wanted to chill before the wedding on Saturday and the place had everything, great...
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    About this property
    You'll love this Oak Bluffs vacation rental with plenty of entertainment and a beautiful gourmet kitchen! The surrounding area is quiet and residential, and the water is less than a mile to the northwest. To get to the heart of Oak Bluffs and its shops and restaurants, it's just a mile to the...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    Welcome Martha's Vineyard, all people, local/foreign/happy/LGBT/Spiritual-not! Our home is located across from Norton's Farm and public transportation. Car and motorbike are best to access everything from this location. Our location is quiet, cozy and convenient all at the same time. Located on...
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    Oak Bluffs, Martha's Vineyard 02557
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
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    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    'It's an amazingly quaint spot with perfectly manicured landscaping'.. 'You have an amazing home' With a bit of reconstruction we transformed a fishing cabin into a cozy cottage with romantic gardens. Perfectly suited for a couple or small party seeking privacy and solitude. The graceful grounds...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 3
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    A deck, an enclosed yard - walking distance to the beach, ferry & town!1 / 29
    (1)Terrible
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Smoking allowed
    About this property
    Enjoy one of the most enviable locations on Martha's Vineyard when you stay at this four-bedroom Oak Bluffs home, a beautifully renovated Victorian with a fenced yard, a porch and deck with accommodations for up to 10 guests. This two-level house sits just half a mile from the Steamship Authority...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    1 Bedroom, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
    About this property
    Coastal comfort awaits at this lovely Martha's Vineyard condo, tucked only a few minutes by foot or car to the island's famous beaches! And with amenities ranging from tennis to golf and a shared outdoor pool, there's no better way to treat yourself to a perfect getaway. Part of a beautifully...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 6
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    Heated Pool, Hottub,AC,WiFi,sleep22, 2 mi to beach1 / 49
    (1)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 22 Quick View
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    • Hot Tub
    • Cable/satellite TV
    • Washer
    • Patio
    • Grill
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This upscale, newly renovated, 4 bedroom home in a quiet neighborhood in Oak Bluffs. You are 2.5 miles from the town center and Inkwell and State beautiful public beaches. This home boasts a large unground back yard pool and hot tub on the mahogany deck. Large outdoor shower. Grill and fire pit...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 22
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    Ocean, lake, harbor and parkview Vineyard cottage1 / 17
    (2)Excellent
    6 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Wi-Fi
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterview - located on the East Chop Vineyard Highlands overlooking Nantucket Sound, Oak Bluffs harbor, Sunset Lake, and 3 acre Washington Park, this charmingly original 1860's Vineyard cottage is an ideal family vacation home. Leave the car on the mainland or in the driveway, for everything,...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Adorable waterfront cottage, pristinely maintained throughout the years. Enjoy privacy and and gorgeous water views of the lagoon from the spacious deck. Wade across th generally ankle deep inlet in front of the house, 3 minute walk over to great sandy lagoon beach - a perfect place for young...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Secret of Life1 / 14
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Cable/satellite TV
    • Balcony
    • Porch
    • DVD Player
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 July 2017
    Secret of Life is a really excellent holiday home. It is spacious, modern andcomfortable and within easy walking distance of the lovely Oak Bluffs. The owners had taken the...
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    About this property
    JUNE & JULY RATES REDUCED!! You will be within walking distance from downtown shopping, movie theatre, restaurants, bike path, harbor, beaches, and two-tenths of a mile from the brand-new modern library. Relaxed and warm, this brand-new home is expertly decorated. The open floor plan and two...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Visitors will enjoy this delightful and comfortable four bedroom, 3 bath home in the desirable East Chop area of Oak Bluffs. Relax in the breeze with your morning coffee on the front porch and have afternoon drinks on the back patio. Several gathering areas with beautiful new furniture make...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MVVR EXCLUSIVE: Adorable, pristine beach cottage has spectacular views across the sound, calm water swimming, great area for kayaking. The open kitchen, dining and living areas are enhanced by the wall of windows facing the waterfront and providing gorgeous water views . Enjoy the parade of...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 4
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    7 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New for 2018: All new Kitchen being completed at this time, not shown in current photos. Large families looking for a true shore experience will enjoy this delightful,whimsical, large historic summer home with cottage details set on the edge of Harthaven Harbor. The home boasts spectacular...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious tri-level contemporary home in the desirable Oak Bluffs community of Meadow View Farms. Conveniently located close to downtown Oak Bluffs with easy access to both Vineyard Haven and Edgartown, This home sits at the edge of a multi-acre conservation area with bountiful trees surrounding...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Situated just on the outskirts of Oak Bluffs this lovely new vacation home offers renters modern styling with multiple living space,s and all the conveniences renters look for in a vacation home. Outdoor highlights include, a farrmers porch with porch swing and adirondack chairs and a private...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This wonderful four bedroom home is conveniently located in Oak Bluffs is just off the bike path and less than two miles to downtown Oak Bluffs. Inside the home offers an open floor plan with chefs kitchen, comfortable living room and dining room with cathedral ceilings and beautiful fireplace. Two...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Grill
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious and perfect for extended families, featuring multiple attractively furnished living areas and sleeping 13 comfortably. The lower level of the house features a queen bed, kitchenette, den area with TV and full bath. The main living level hosts a living room, family/TV room, large and...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 13
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    Extended families are sure to enjoy this Tri-level home featuring open floor plan on the main level, large main living room and two den TV areas one on the first level one and an additional TV area on the 2nd level. Kitchen has stainless appliance and granite counters and the family dining area...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This welcoming air conditioned waterfront house and guest house is privately set with panoramic water views of Lagoon Pond, Hines Point, the draw bridge, Vineyard Sound and Cape Cod. The main house has a generous open layout with substantial living room, dining, and sitting areas that allow for...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    This gorgeous, contemporary air-conditioned private home is perfect for your luxurious vacation on the island. It is 2700 sq ft of well laid-out space and sits on 1.4 acres of land in a private wooded area, centrally located, only minutes from downtown Oak Bluffs and beautiful beaches. The...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Newly Renovated with Fabulous ocean views1 / 19
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Ocean Views
    • Housekeeping Included
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This magnificent 1920’s East Chop cottage has been extensively redesigned, refurbished and expanded to allow friends and families to enjoy luxury accommodations along with rare double views of both Nantucket Sound and neighboring Crystal Lake. Complemented with a huge wrap around deck and a covered...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Cable/satellite TV
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    Smoking allowed
    About this property
    This adorable Gingerbread cottage is located only a block to town and a couple of blocks to the beach. You can enjoy morning coffee on the covered wrap around porch that leads into a cute sitting room with a TV and another small sitting area off of the front room. There is also a nice size dining...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is our beautiful home on Martha's Vineyard we call Shangi-La! Spectacular setting with a great peaceful view overlooking Sengekontacket Pond with the Ocean beyond. The property features a shared Pool, Tennis Courts, and a Dock. Our house is conveniently located midway between the Oak Bluffs &...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    About this property
    Pristine 4 bedroom waterfront hideaway. Enjoy spectacular views and sunsets across the lagoon. Private dock for boat enthusiasts. Kayak and boat rentals can be delivered to the property and kayaking on the lagoon is a fun and picturesque activity for the entire family. Centrally located, you...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious sun filled contemporary home located on a quiet private street,a 10 minute walk to town center, Inkwell Beach and harborfront, The first level features a spacious kitchen with stainless steel appliances, prep counter with range top. and breakfast nook, there is a comfortable living area...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    10 minute walk to Oak Bluffs center and beach area from this lovely modern vacation home. Enjoy all that the summer community of Oak Bluffs has to offer, quaint shops, fine and family dining, harbor front stroll where you will and array of dining establishments, all waterside, boat rentals and...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sweet, little (it's priced accordingly!)cottage is all about convenience. It is within walking distance to the center of Oak Bluffs and two town beaches. The interior of the cottage has recently been redone inside and is fresh & clean and perfect for a great vacation. Large decks, lovely...
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    Oak Bluffs, Martha's Vineyard 02539
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
    • Air Conditioning
    • Housekeeping Included
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fabulous 125 year-old Victorian cottage was lovingly updated and completely restored in 2012. Sitting on a large private lot, just steps from Inkwell beach, Solera offers the perfect balance of comfort, ambiance and vintage charm. The large, airy gourmet kitchen was featured in This Old House...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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    WATERFRONT HOME WITH PRIVATE BEACH1 / 25
    (1)Excellent
    7 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on over 1 acre of waterfront property on East Chop, an exclusive area of historic Oak Bluffs, this unique home is perfect for family and friends that want to vacation together while allowing for separation. This home can accommodate up to 12 people. No longer need to rent multiple homes on...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    About this property
    For those who love an in-town location this area known as the Campground with the historic Tabernacle is the ideal location. The sweet and colorful cottage is pristinely maintained by the owner. Rockers line the porch for your outside enjoyment. The main level hosts the living room with TV (...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    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 living level features an open concept and hosts a family TV room and luncheon breakfast...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recently updated this lovely 4 bedroom, 3 bath contemporary home features an open floor plan in the living and kitchen areas opening to the covered porch and seating area on the front of the house and the deck and patio dining area off the back of the house. The main living room is centered around...
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    Location Information
    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New Listing for 2018 Summer Season! Interior features, main living area, lower level family room, open kitchen and dining area, five bedrooms including two master bedrooms en-suite, two bedrooms on 2nd level that share a hall bath and children's/teen bunk room on the lower level and a bath located...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely Summer Home located in Waterview Farms a private community on the outskirts of Oak Bluffs ******* Sengekontacket Pond, ( saltwater in inlet from the North Shore). This special home boasts beautiful views across peaceful meadows to Sengekontacket Pond and the North Shore beyond. Launch...
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    Location Information
    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fabulous Gingerbread In The Heart Of OB!1 / 23
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Wi-Fi
    • Waterfront
    • Ocean Views
    • Air Conditioning
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    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2018
    We rented 8 houses in the neighborhood for our son’s wedding. We could walk everywhere and the porches were great for welcoming visitors. Surely it used to be a boarding house...
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    About this property
    Spacious gingerbread directly across from Union Chapel. Sit and watch the action roll by from the comfort of large front porch or enjoy the quiet and private yard/patio on the side of the house. Even though there are 3 parking spots on the premises the location affords you the luxury to easily walk...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Washer
    • Patio
    • Cable/satellite TV
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy the island at this adorable renovated cottage within walking distance to town. The home is approximately half mile walk to the harbor and town beaches. The home is tastefully decorated from top to bottom. The first floor features and open kitchen with stainless steel appliances that...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Charming 4 bedroom home in the east chop neighborhood of Oak Bluffs1 / 5
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Parking
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2017
    My family had a wonderful time staying in this surprisingly spacious vacation cottage. It had a very home-y feeling to it, and plenty of room for all of us. The kids could...
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    About this property
    Adorable 4 bedroom cottage in the East Chop neighborhood of Oak Bluffs. You will love the beautiful back yard that has a patio and sizable garden and is very private. There is a large screened porch for entertaining. Inside are four comfortable bedrooms and two baths plus an outdoor shower. The...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set in a quiet community of homes just on the outskirts of OB, this outstanding home provides a peaceful get away yet is just a short drive to town center and public beaches The use of coastal colors and upscale furnishings throughout combine to make this gorgeous Oak Bluffs summer home a cut a...
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    Oak Bluffs, Martha's Vineyard 02536
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute and Cozy guest house with open floor plan in the kitchen, living and alcove sleeping area with queen bed. This cottage is perfect for couples, the owner will consider one additional child. There is a den with futon sofa separate from the main part of the cottage. Relax on the deck while...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend an unforgettable summer on the beaches of Martha's Vineyard when you retreat to this two-bedroom townhouse, a charming Oak Bluffs escape with a private deck, a shared swimming pool and tennis courts, and easy walking access to downtown and nearby beaches. Please be aware this rental has a...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    In-Town Historic Property on Martha's Vineyard1 / 20
    (68)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Cable/satellite TV
    • Grill
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2018
    Firstly, we were travelling from the U.K. In our view, the apartment needs attention internally and we were disturbed until the early hours by a resident and staff of the nearby...
    Reviewed 12 June 2018
    I enjoyed the entire trip to no end. The stay was excellent the location perfect. You are in a great town Oak Bluffs you’re with in walking distance to everything you could...
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    About this property
    This Oak Bluffs, Martha's Vineyard rental is a certified National Historic Property. Ideal location for visitors in the middle of the most active, multi-cultural, charming, and fun town on Martha's Vineyard. Step outside your door for breakfast or ice cream, a great selection of restaurants in...
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    Oak Bluffs, Martha's Vineyard 02557
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    “Gingerbread House”, water views, large porch!1 / 12
    (1)Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Terrace
    • Grill
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New Renovated, 1870 historic 'Campground' cottage centrally located in Oak Bluffs, The cottage has 4 bedrooms (all located on the second floor) - 1 queen, 2 double beds and 2 twins beds. The front bedroom has its own balcony with water views. Cottage sleeps 8. the first floor includes a newly...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Meadow View Farms home, bordered by expansive landscaped yard, peaceful private setting. Association tennis courts just a short distance from the house and Farm Neck Golf and Tennis is just a half mile from the house. Miles of connecting bike paths begin at the entrance to this lovely...
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    Oak Bluffs, Martha's Vineyard 02568
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautiful Colonial in Oak Bluffs with Air Conditioning1 / 27
    (1)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 13 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 August 2013
    Nice, clean, updated home with space for everyone. We divided older teen girls in upstairs dorm style rooms that slept 5 from you get boys and girls in two rooms that slept 2...
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    About this property
    Newly renovated 5 bedroom home just a mile and a half from the center of Oak Bluffs. New hard wood floors throughout as well as updated furnishings and decor. Dining area is extended by a nice sized sunny deck for outdoor dining. Perfect for a large family vacation. Additional amenities: Coffee...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 13
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    Historic home with gorgeous antiques and modern conveniences1 / 40
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Balcony
    • Internet Access
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This classic Oak Bluffs home is filled with antiques and has views of the pier from the front porch. It's the perfect home for families wanting a relaxing getaway. This historic cottage is only five minutes away from Ink Well Beach and the Steamship Authority Dock, and is just a half mile from...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bright, airy contemporary home located in the wonderful East Chop neighborhood. The first floor features an open concept living room and kitchen. The kitchen has a large island that can seat seven. First floor bedroom is located off of the living room and has access to the full bath. The second...
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    Oak Bluffs, Martha's Vineyard 02557
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 7
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