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Latest Vacation Rentals in Chilmark MA (25)

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2 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

Japanese inspired, Mid-Century Modern beach house with sweeping views of Menemsha pond, Vineyard sound, Aquinnah. Pond access via path. Stunningly bright and fully renovated in '20 with open...

Created May 19, 2024

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4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts

MUDDROOM: Large Closet, Air Conditioner, Stocked with Beach towel's.KITCHEN: Granite counter top's, Dishwasher, Gas Viking Stove and fridgerator, Microwave, Toaster oven, Espresso/Coffee maker....

Created May 19, 2024

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2 Br Cottage Vacation Rental In Chilmark, Massachusetts

Charming rustic cottage located a short distance off South Rd just past Abels Hill in Chilmark. Chilmark is very rual with rolling hills and stone walls. Water views from upper deck. Access to Lucy...

Created May 19, 2024

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7 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR ANY STAYS LESS THAN 7 NIGHTS, THE NIGHTLY PRICE WILL INCREASE. PLEASE SEND THE...

Created May 19, 2024

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2 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

This guesthouse is a 2 Bedroom private home in peaceful and secluded Chilmark neighborhood.Spacious outdoor space with 8 people outdoor dining, wood burning fire pit, BBQ grill, 6 person hot tub...

Created May 19, 2024

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4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts

Bring the kids and dogs for a fun relaxing stay in the secluded Aquinnah end of Martha's Vineyard. Our home is rustic and decorated in a shabby-chic style with many antiques mixed with Pottery...

Created May 19, 2024

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5 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

This private Chilmark compound has breathtaking views out to the Atlantic Ocean and 1/3 mile of private beach in your backyard. It sits on 19+ acres on the Wequobsque Cliffs providing a secluded...

Created May 19, 2024

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1 Br Apartment Vacation Rental In Chilmark, Massachusetts

Small, but cozy bedroom with smart TV, kitchenette with microwave, refrigerator, toaster oven and Keurig coffee maker. Use of heated swimming pool. Outdoor shower.Weber grill and table for two...

Created May 19, 2024

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4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR ANY STAYS LESS THAN 7 NIGHTS, THE NIGHTLY PRICE WILL INCREASE. PLEASE SEND THE...

Created May 19, 2024

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4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

*We secured ferry reservations for you*-June 1 and 8: Discounted Rates -August 24 and 31-August 31 and September 7Enjoy spectacular panoramic views of the ocean, dunes, beach and Squibnocket Pond....

Created May 19, 2024

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2 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts

Welcome to our getaway. The Up-Island Treehouse offers an open, light-filled and breezy spot on the western tip of Martha's Vineyard. Here you can relax and unwind in comfort and take your time to...

Created May 19, 2024

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2 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

Chilmark Guest HouseOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Tucked away in a private glen on three...

Created May 19, 2024

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3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

*** Please make an inquiry before booking. ***This quintessential Up-Island 1920s summer house has panoramic water sunsets thanks to its hillside position overlooking the Vineyard Sound. (An East...

Created May 19, 2024

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1 Br Cottage Vacation Rental In Chilmark, Massachusetts

Located in Menemsha Village. This quaint cottage is located a stones throw from the Menemsha Harbor. It is the smallest and most affordable of the three houses we rent, yet offers great views.The...

Created May 19, 2024

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4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts

This spectacular beach house with stunning water views is located 20 feet from the edge of a grassy cliff overlooking Vineyard Sound. It was designed by the visionary architect Andrew Geller and is...

Created May 19, 2024

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4 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts

Location Location: Beachfront home on Lobsterville Beach in Aquinnah, This wonderful beach house is waiting for you! Enjoy the cathedral ceilings in the living room, large kitchen, den and dining...

Created May 19, 2024

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5 Br Private Vacation Home Vacation Rental In West Tisbury, Massachusetts

Deep Bottom PondOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Set your sights on this high-end neighborhood...

Created May 19, 2024

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4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

Spectacular light large home with beautiful water views towards the Vineyard Sound and Naushon Island. The light open kitchen/living is in the middle of the house, leading down to the 4 bedrooms +...

Created May 19, 2024

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2 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts

This well-furnished and architecturally unique two-to-three bedroom house is located on 2.5 secluded acres in Aquinnah. The house has gorgeous 180 degree water views and the private beach is just a...

Created May 19, 2024

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3 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts

Three Winds is a modern beach home on Martha's Vineyard available for rent year-round by the week. It is located in Aquinnah, the island's westernmost end. The house sits on windswept rolling...

Created May 19, 2024

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3 Br Private Vacation Home Vacation Rental In Aquinnah, Massachusetts

Spacious and comfortable beach cottage on 2 secluded acres in prime Aquinnah location, dripping with quintessential MV character and charm. Perched on a hill with 180 degree views of Vineyard Sound...

Created May 19, 2024

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6 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR ANY STAYS LESS THAN 7 NIGHTS, THE NIGHTLY PRICE WILL INCREASE. PLEASE SEND THE...

Created May 19, 2024

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4 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

A brand new listing! You are very welcome to this peaceful, quiet and private house in Menemsha village, just minutes from the public beach, harbor, restaurants, shops and galleries. The location...

Created May 19, 2024

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3 Br Private Vacation Home Vacation Rental In Chilmark, Massachusetts

Wayside CampOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Conveniently located in the center of Menemsha,...

Created May 19, 2024

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4 Br Cottage Vacation Rental In Chilmark, Massachusetts

Our waterfront cottage on Chilmark Pond is a short wade to a stunning barrier beach on the Atlantic Ocean and has a lovely view on the pond from the front deck. There is access to Abel Hill...

Created May 19, 2024

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