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Oak Bluffs Holiday Rentals

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    Travellers to Oak Bluffs are booking June dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 22
    5 of 5 bubbles (3) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 bubbles (2) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    4.5 of 5 bubbles (3) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Beautiful home in a quiet area, near all the shopping. Walk to beaches and the center of Oak Bluffs. On the bus line between Oak Bluffs and Vineyard Haven/Tisbury. Contemporary style, full kitchen, outdoor shower, deck and grill, parking. Sunny and private and feels like it's in the woods. Two... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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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    Oak Bluffs, Martha's Vineyard 02557
    1 / 23
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 16
    3 of 5 bubbles (2) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Terrace
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    About this property
    Adorable GINGER BREAD house in Oak Bluffs that I rent out for 6 weeks each summer. Best location! It's a 2 minute walk to the harbor, town restaurants, shops and bars. The OCEAN is a 6 minute walk! House is adorable, furnished, AC in some rooms, parking. Overlooking a park, sip your coffee on the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 17
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    This is an old farmhouse consisting of 2 floors with 3 bedrooms on the second floor and 1 on the first floor. One queen and 3 doubles. A large living room and bath on the first floor. In the kitchen is a Refrigerator, gas stove with oven, a washer and dryer and a dishwasher. There is a portable... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    5 of 5 bubbles Reviewed 22 August 2014
    So often descriptions fall short of reality but our stay at this Flip-key rental was as it was toted, a "Charming Farmhouse." The four bedrooms were sweet and spacious decorated...
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    1 / 11
    4 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Balcony
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    • x
    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 7
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Outdoor Dining Area
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    About this property
    A comfortable ranch with all the amenities for a perfect vacation. It's quiet location is 1.5 miles from town, yet not too far to bike or walk in when needed. Beaches, ponds, the lagoon, and other recreational facilities are also easily accessible if you want to hop on the bike path around the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    1 / 9
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Beautiful and spacious 3 bedroom in Oak Bluffs, Martha's Vineyard. Sunny, open and airy Cape. Walking distance to town, gingerbread cottages, library, and playground. Close to beach, golf course, and great fishing spots. There is a pack and play in the upstairs bedroom for a baby to sleep or nap... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 44
    2 of 5 bubbles (1) Poor
    6 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    *Fall/Winter/Spring multi-week discount available *Only 1 prime summer week left! Check my calendar and book ASAP if you plan to visit in the peak season. *Perfect location so No Car Needed. Easy walk to town, beach & parks. The Pennacook house in Oak Bluffs on the charming island of Martha's... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 22
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Just a block from the East Chop Bluffs on a sleepy side street in a quiet wooded setting. There are 2 SEPERATE LIVING ROOMS!! Large bright kitchen that accesses a separate dining room, inviting screen porch with dining and sitting areas, and sunny rear deck with lots of backyard privacy. Ocean... View all property information
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    Oak Bluffs, Martha's Vineyard 02257
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    About this property
    Home away from Home! Walk to Sailing Camp! Bright, sunny 3 bedroom Cape style vacation home in Lagoon Heights with great amenities. Fully furnished home with 2 baths, outdoor shower, large deck and private enclosed yard and a wonderful deck for the summer cookouts. Open floor plan with spacious... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 94
    3 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Satellite TV
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    • Ocean Views
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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 &... View all property information
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    Oak Bluffs, Martha's Vineyard 02539
    1 / 14
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Satellite TV
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    • Pet-friendly
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    • x
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    • x
    About this property
    JUNE & JULY RATES REDUCED!!<BR><BR>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.<BR><BR>Relaxed and warm, this brand-new home is expertly decorated. The open floor plan... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 61
    5 of 5 bubbles (1) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 22 | Quick View
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    • Hot Tub
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 6
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Beautifully Appointed Renovated 2 Bedroom Cottage close to Lagoon Heights Beach. Bedrooms have cozy Queen Beds with Ceiling Fans. 1 Bathroom with Large Soaking Tub,and Outside Shower with Hot Water. Breezy , Quiet , Large Yard Parking For 2 Cars Open Living Dining Kitchen Area. Outside Patio... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Central Heating
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    For your next getaway, escape to this fabulous 3-bedroom, 2-bathroom Oak Bluffs vacation rental condo that comfortably sleeps 5. Steps away from the beach, this condo offers beautiful ocean views and comfortable accommodations. Whether you’re seeking time on the beach or an art-inspired getaway,... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    1 / 19
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • x
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • x
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    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 10
    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 17
    5 of 5 bubbles (2) Excellent
    6 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
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    • Pet-friendly
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    • x
    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,... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 22
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • DVD Player
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    • Pet-friendly
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    About this property
    Historic summer "cottage" with 7 bedrooms, sleeping porches, a deck overlooking the water, a private dock on Harthaven Harbor, and immediate access to the ocean. The rustic home is a perfect gathering spot for family and friends. It has a large living room with a huge stone fireplace, an eat-in... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 30
    4 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
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    About this property
    New to the 2015 Summer Season! This spacious waterfront home offers 4-bedrooms en-suite, with family, game and fitness rooms...and yes, a pool. The peaceful setting is centrally located, yet close to the village center for easy access to shops, restaurants and more. The home is tastefully... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 5
    4 of 5 bubbles (3) Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Central Heating
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    • ?
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    About this property
    This 4 bedroom home with skylights, 52 inch Tv, computer, internet, printer, fax, is your home away from home. 1 mile from town 1.5 mile from beach and 7 miles from airport is ideal location. 2 SETS OF GOLF CLUBS AND 4 TENNIS RACQUETS FOR YOUR USE, 3 CABLE TV'S, MASTER BATH HAS WHIRLPOOL TUB... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    5 of 5 bubbles Reviewed 9 September 2016
    Before choosing this property, I referenced other review sources (i.e., AirBnB) and am glad I did. I found the property to be a great find: well appointed, nestled in a quiet...
    5 of 5 bubbles Reviewed 8 September 2016
    Family members from CT, MD, NJ and NY gathered here for the Labor Day weekend. It was vary comfortable, convenient to downtown and quiet. 4 bedrooms and a pull out couch for the...
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    1 / 24
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    Escape to the perfect island getaway at this gorgeous, recently renovated Oak Bluffs home on lovely Martha's Vineyard. Light-filled bedrooms, a playroom, and a huge deck await! Downtown Oak Bluffs is nearby and it's only one mile to the water. If you'd rather remain on the property, you're... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Relax in optimal comfort at this Oak Bluffs home. It's got four bedrooms and lots of space for an ideal family vacation! You're in the heart of Oak Bluffs, within walking distance of the harbor and lovely waterfront. You can hop off the ferry to Martha's Vineyard and be here in no time. This... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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 the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 29
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    About this property
    It's all about the stellar location of this five-bedroom Oak Bluffs getaway, a wonderfully renovated Victorian home with a front porch and deck, four bikes to help you explore Martha's Vineyard, and an enclosed yard that is ideal for kids. This two-level house sits just half a mile from the... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 29
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    About this property
    Soak in one of the loveliest sunset views on Martha's Vineyard when you escape to this two-bedroom Oak Bluffs cottage, where you'll enjoy a short walk to the ferries and a private deck with panoramic views of Lagoon Pond, Brush Pond, Vineyard Sound, and Vineyard Haven. This single-level cottage... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Tucked away among the shade trees on Martha's Vineyard, this delightful cabin in the woods is ideal for your next family vacation or getaway with a few close friends. This three-bedroom rental is located less than a mile from the top-ranked, semi-private Farm Neck Golf Club as well as the Trade... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 20
    8 Bedrooms, 8 Bathrooms, Sleeps 20 | Quick View
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    About this property
    Amazing five acre property! 6 BR main house w/ pool + a 2 BR carriage house! Our amazing property is perfect for everything from a memorable family vacation to a serene retreat. You and your guests will begin to enjoy the feeling of privacy the minute you arrive as you drive down the long tree... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Experience the beauty and charming attractions of the Nantucket Sound in this high-end home offering phenomenal New England decor for groups of six. The stylish home offers detailed features like an outdoor shower, stained glass windows, and hand-painted tiles from Jerusalem making it more than... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 25
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Parking
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    • x
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    About this property
    Stay in this peaceful, well-maintained home with a large wrap-around porch, a deck, and in close proximity to the ocean for your next unforgettable New England vacation. Come with a small group of friends, bring your own small family, or get away with another couple and rest assured that you'll... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 38
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Sea breezes and fabulous water views from almost every room are the mainstay for this unique waterfront home on the Lagoon Pond in Oak Bluffs. Polished with soothing designer furnishings in layers of cappuccino and white neutral linen and cotton, you will enjoy this European-chic interior almost as... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 27
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • x
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    About this property
    MVVR EXCLUSIVE: Custom crafted tri-level, this beautiful sun filled home features, spacious open living spaces, hardwood floors throughout, sleeps 8 with 2 King Masters en-suite, guest king bedroom and semi-private Alcove sleeping area on the 2nd level ( see photo 23) Exterior features include two... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 34
    4 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    This is a beautiful waterfront home with a pool on the Lagoon. Enter through the impressive foyer with waterviews over the pool and lawn. There is a large living room with cathedral ceilings and dining area on the main level. There is a gourmet kitchen with eat-in dining overlooking the pool. The... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 20
    5 of 5 bubbles (59) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • DVD Player
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    • Porch
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    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... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    5 of 5 bubbles Reviewed 13 November 2016
    This rental is the best place to stay for our family. We've been returning every year to stay at the Historic Arcade Building for about 8 years. The location is perfect, walking...
    5 of 5 bubbles Reviewed 11 October 2016
    We have been staying at this apartment for years now. We look forward all year to going back to the same place. We now have come to refer to it as home! We love the location as it...
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    1 / 28
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    About this property
    This wonderful family vacation home features lovely waterviews across Crystal lake. The peaceful location and large yard provide the perfect venue for extended families with children. Relax on the expansive deck, enjoy the views from the 4 person glider swing as seen in the photos Families will... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 20
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    European-styled cottage is tucked away down a private lane surrounded by private yard with gardens - you’ll feel like you have completely gotten away from it all. The front door opens into a classic Mudroom with an antique wood, stadium bench seat - and then you step into the open and airy Great... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    If you are looking for an immaculate, charming, cottage style, yet modern home and close to Oak Bluffs center look no further. This recently updated 3 bedroom, 2 bath home features sunny open living, kitchen and dining areas. Soft seashore color palette throughout adds to the ambiance of this great... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 25
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    • Pet-friendly
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    • x
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    • x
    About this property
    Adorable waterfront cottage, pristinely maintained throughout the years. Enjoy privacy and views from the spacious deck. 3 minute walk to great sandy lagoon beach - a perfect place for young children to play. Centrally located just 2 miles to either Vineyard Haven or Oak Bluffs town centers.... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 22
    4 of 5 bubbles (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
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    • Hot Tub
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    • Pet-friendly
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    • x
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    • x
    About this property
    Walk to town from this meticulously maintained, large & airy, 3 bedroom, 3 full bathroom vacation getaway, located on a beautiful 1/4 acre lot on a quiet street. Watch your troubles sail away while relaxing on the large farmer's porch with your favorite summer beverage, or grilling with family and... View all property information
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    Oak Bluffs, Martha's Vineyard 02557
    1 / 19
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • x
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    • x
    About this property
    Tiny beach cottage, a rare find these days and just perfectly cute. The cottage is located along the waterfront on East Chop Drive, a very desirable area of Oak Bluffs. The porch looks out over the beach and beyond to the Vineyard Sound. Relax on the covered porch and take in the outstanding... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Note: Interior photos are of a unit with same floor plan, see details below for description of decor of unit not shown in these photos. Waterfront Seaview Condo # 205 is a corner unit and is being all newly painted and furnished for Summer 2017. Photos of completed unit will be available late April... View all property information
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    Oak Bluffs, Martha's Vineyard 02568
    1 / 13
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Families are sure to enjoy this cozy home with nautical inspired decor. The main living level offers a spacious living and dining area with cathedral ceiling cooled by window AC. and a neat well equipped kitchen with pass through window. The kitchen opens onto a spacious deck with patio dining and... View all property information
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    Oak Bluffs, Martha's Vineyard 02536
    1 / 35
    5 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • x
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    • Smoking allowed
    • x
    About this property
    Privately situated on a hilltop in Sengkontacket, -spacious tri-leve 4000 sq ft 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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    Oak Bluffs, Martha's Vineyard 02568
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    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
    Location Information
    Oak Bluffs, Martha's Vineyard 02568