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$1,143

4 BR / 0 BA / Sleeps 10

#2001  3+ acres overlooking the Elizabeth Islands & beyond - Chilmark vacation rentals
1 / 26

$1,143

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#2001 3+ acres overlooking the Elizabeth Islands & beyond

Chilmark house
4 BR / Sleeps 10 | Quick view

Details

Spectacular waterviews! This Martha's Vineyard vacation rental is situated on 3+ acres overlooking the Elizabeth Islands and the Vineyard sound. On a clear day you can catch a lovely view of the Aquinnah lighthouse. The outdoor living space is truly where you want to be. Each area used for various activities such as …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$179

2 BR / 1 BA / Sleeps 4

Menemsha Sunsets on the Deck 116552 - Chilmark vacation rentals
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$179

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Menemsha Sunsets on the Deck 116552

Chilmark house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Nice two bedroom cottage located in the heart of Menemsha. Watch the beautiful sunsets from the deck while dining. Five minute walk to beach, fish market or quaint shops in this fishing village. Additional amenities include: coffee maker, smoke free, 4 dining capacity, lobster pot, 1 trundle(s), vacuum cleaner, …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$150

4 BR / 2 BA / Sleeps 9

Chilmark Contemporary Cape with Access to Beaches 116588 - Chilmark vacation rentals
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$150

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Chilmark Contemporary Cape with Access to Beaches 116588

Chilmark house
4 BR / 2 BA / Sleeps 9 | Quick view

Details

Spacious and comfortably furnished contemporary Cape is conveniently located between Chilmark and West Tisbury. House is fully equipped, open living area with cathedral ceilings, wood floors, operable skylights, large outdoor deck and separate family room with sleeper sofa. Private setting with access to Chilmark …
  • Internet Access
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$143

3 BR / 3 BA / Sleeps 8

Wonderful Three Bedroom Up-Island Retreat 116582 - Chilmark vacation rentals
1 / 14

$143

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Wonderful Three Bedroom Up-Island Retreat 116582

Chilmark house
3 BR / 3 BA / Sleeps 8 | Quick view

Details

This wonderful three bedroom up-island retreat, is the perfect summer vacation home, with lots of room to spread out. The master bedroom on the first floor offers great light in the morning sun with ensuite bathroom. The second floor with two bedrooms, shared bathroom and small office area on the second floor offers a…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

3 BR / 2 BA / Sleeps 6

Cozy, Charming Three Bedroom Cape 116554 - Chilmark vacation rentals
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$358

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Cozy, Charming Three Bedroom Cape 116554

Chilmark house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

This charming newly remodeled three bedroom, two bath Cape has a spacious master bedroom suite, cozy sun room and updated kitchen. Spend your Chilmark vacation here and enjoy rights to desirable Lucy Vincent and Squibnocket beach. A memorable up-island retreat awaits you! Additional amenities include: coffee maker, …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$229

1 BR / 1 BA / Sleeps 4

Menemsha Dream Cottage Overlooking Harbor 114931 - Chilmark vacation rentals
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$229

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Menemsha Dream Cottage Overlooking Harbor 114931

Chilmark house
1 BR / 1 BA / Sleeps 4 | Quick view

Details

Kick back and relax in this beautiful one bedroom cottage overlooking Menemsha Harbor. Shop at the Menemsha General Store, fish from Dutcher Dock, and swim at Menemsha Beach, or enjoy a lobster dinner while watching sunset from the balcony of your upstairs living room. A little slice of heaven awaits you in this …
  • Waterfront
  • Deck
  • Linens Provided
  • Microwave
  • Stove or Oven
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,429

3 BR / 4 BA / Sleeps 6

1 / 21

$1,429

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Beautifully Restored Antique Cape 113602

Chilmark house
3 BR / 4 BA / Sleeps 6 | Quick view

Details

Beautifully renovated and restored antique Cape situated in Chilmark on two ponds. Three bedroom home plus loft area. Tastefullly furnished throughout with full modern amenities. Living room, dining room as well as an eat-in kitchen. Includes a game room with pool table and sitting area for relaxing and enjoying …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Patio
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$2

4 BR / 0 BA / Sleeps 8

1 / 13

$2

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#2059 Access to Lucy Vincent & Squibnocket Beaches

Chilmark house
4 BR / Sleeps 8 | Quick view

Details

Four Bedroom Cape located in Chilmark on a circular drive. This Martha's Vineyard vacation rental offers private back yard with large deck for out door dining and sunning. Access to Lucy Vincent and Squibnocket Beaches just up the road. Additional amenities include: beach chairs, outdoor shower: enclosed, ipod dock, …
  • Internet Access
  • A/C or climate control
  • Deck
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$929

5 BR / 0 BA / Sleeps 10

1 / 15

$929

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#2057 Elegance & style in private setting w/ key to Quansoo

Chilmark house
5 BR / Sleeps 10 | Quick view

Details

Vacation in Chilmark on the pristine shores of the Tisbury Great Pond in this custom contemporary built with only the best materials. Four-bedroom main house with a detached guest suite. Open living/Dining/kitchen area with cathedral ceilings and exposed beams overlooking a luxurious setting by the fireplace. Separate…
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$429

4 BR / 0 BA / Sleeps 10

1 / 19

$429

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#2029 Elegant Architectural Digest Cape home in Chilmark

Chilmark house
4 BR / Sleeps 10 | Quick view

Details

Elegant Architectural Digest Cape home in Chilmark, in pristine condition. Many fine details to this Martha's Vineyard vacation home. Custom woodwork, antique heart pine floors and fireplaces. Luxury construction (as compared to custom) built in 1998. Custom cabinetry with gourmet kitchen. Meadowed lot with stone …
  • Internet Access
  • Deck
  • Dishwasher
  • Microwave
  • Toaster
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$172

3 BR / 0 BA / Sleeps 6

1 / 12

$172

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#2025 Delightfuf guest house with sweeping water views

Chilmark house
3 BR / Sleeps 6 | Quick view

Details

Delightful Cape GUEST HOUSE situated on the grounds of a hilltop Chilmark estate. (Estate's Main House is rented separately and may be occupied). Magnificent views over Menemsha Pond. Access to Hancock Beach with adjacent parking and Menemsha Pond within walking distance. First floor has an open kitchen, dining and …
  • Ocean or water views
  • Internet Access
  • Fireplace
  • Deck
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$558

5 BR / 0 BA / Sleeps 10

1 / 17

$558

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#2020 A grand summer house, where memories are made

Chilmark house
5 BR / Sleeps 10 | Quick view

Details

A grand summer house on Martha's Vineyard where memories are made. This landmark, hilltop Victorian offers magnificent 270-degree views over meadows, Menemsha Pond and the North shore. Access to Hancock Beach with adjacent parking, as well as Menemsha pond within walking distance. Two spacious living rooms, front hall…
  • Ocean or water views
  • Internet Access
  • Deck
  • Grill
  • Dishwasher
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

2 BR / 0 BA / Sleeps 5

1 / 9

$215

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#2006 Post & beam vacation home in a lovely rural setting

Chilmark house
2 BR / Sleeps 5 | Quick view

Details

Post and Beam Martha's Vineyard vacation rental in a lovely rural setting in Chilmark. Two bedrooms with large decks and distant waterview of Lucy Vincent beach. Additional amenities include: wood stove, television: regular, outdoor shower: enclosed, check in time: 2:00, flipkey header: #2006 post & beam vacation …
  • Ocean or water views
  • Deck
  • Grill
  • Dishwasher
  • Microwave
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

2 BR / 1 BA / Sleeps 4

1 / 11

$215

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UpIsland Cottage Nestled in the Woods 116958

Chilmark house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

Nicely renovated cottage nestled in the woods, enjoy the peace and quiet of up-island living. Clean, open interior living area, newly furnished with fully equipped kitchen. Enclosed outdoor shower a must for days at the beach. Perfect getaway cottage, sure to please. Additional amenities include: coffee maker, smoke …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1

4 BR / 3 BA / Sleeps 8

1 / 17

$1

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Set High on a Hill, Enjoy Menemsha Sunsets 116929

Chilmark house
4 BR / 3 BA / Sleeps 8 | Quick view

Details

Set high on the hill, have your own private viewing of the spectacular Menemsha sunset from this multi-level saltbox home. Walk to Menemsha beach or village in just minutes. Bright, cheerful rooms with water views from nearly every room is sure to make your stay an unforgettable experience. Additional amenities …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

1 BR / 1 BA / Sleeps 4

1 / 18

$358

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Private Boathouse at Edge of Stonewall Pond 116925

Chilmark house
1 BR / 1 BA / Sleeps 4 | Quick view

Details

Adorable, private boathouse at the edge of Stonewall Pond. Wrap around deck provides gorgeous views (as well as sound effects) of the pond and the barrier beach beyond, great for swimming! Perfect for a small family or a romantic getaway. An idyllic island retreat. Additional amenities include: dock/boat-slip, …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Porch
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$358

3 BR / 3 BA / Sleeps 6

1 / 17

$358

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Breathtaking Views, Private Beach and Tennis 116922

Chilmark house
3 BR / 3 BA / Sleeps 6 | Quick view

Details

Breathtaking views of the Atlantic ocean, Stonewall Pond, Squibnocket and Nomans Land Island. Home sits on six acres, with private beach and newly resurfaced tennis court. Beautiful up-island getaway. Additional amenities include: coffee maker, smoke free, pets considered, lobster pot, food processor, 1st floor …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$475

3 BR / 2 BA / Sleeps 8

1 / 22

$475

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Beautiful Setting with Spectacular Views 116921

Chilmark house
3 BR / 2 BA / Sleeps 8 | Quick view

Details

Beautiful Chilmark setting, located on Stonewall Pond with spectacular waterviews! The east offers views of Stonewall Pond to the Atlantic ocean. The west offers views of Quitsa Pond to Menemsha Pond. Great outdoor deck perfect for relaxing and/or outdoor entertaining. Large sweeping lawn and mature landscaping …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$1,072

3 BR / 2 BA / Sleeps 6

1 / 20

$1,072

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Waterfront Contemporary on Chilmark Pond 116771

Chilmark house
3 BR / 2 BA / Sleeps 6 | Quick view

Details

Waterfront contemporary home situated on eight secluded acres in Upper Chilmark Pond, great views of pond to ocean. Explore the ponds in one of the boats included. Relax and enjoy the spacious outdoor deck. Additional amenities include: dock/boat-slip, coffee maker, smoke free, ipod dock station, lobster pot, ferry …
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$429

5 BR / 3 BA / Sleeps 9

1 / 15

$429

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Water Views Overlooking Squibnocket Pond 116734

Chilmark house
5 BR / 3 BA / Sleeps 9 | Quick view

Details

Spectacular views overlooking Squibnocket Pond and Atlantic Ocean. Contemporary home with two spacious living rooms. Walk to Squibnocket beach. Private access to Squibnocket pond, canoe provided. Key is also available for access to private Zach s Cliff Beach, maximum two cars. Additional amenities include: coffee …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$215

2 BR / 1 BA / Sleeps 4

1 / 17

$215

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Pond House, Peaceful Waterfront Hideaway 116331

Chilmark house
2 BR / 1 BA / Sleeps 4 | Quick view

Details

What could be a more elegant, peaceful and romantic hideaway for a week than the Pond House? It sits at the conjunction of ocean and land, pond and meadow, with a view beyond dazzling outside and a warm fire in the fireplace inside. Gourmet kitchen. Antique and comfortable furniture. Quality bedding. Toasty. Snug. …
  • Waterfront
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$929

1 BR / 3 BA / Sleeps 8

1 / 12

$929

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Chilmark - Four bedroom with wading pool 126257

Chilmark house
1 BR / 3 BA / Sleeps 8 | Quick view

Details

N/A
  • Shared outdoor pool (unheated)
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$572

4 BR / 2 BA / Sleeps 8

1 / 13

$572

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Chilmark - 4 bedroom with distant waterviews 125237

Chilmark house
4 BR / 2 BA / Sleeps 8 | Quick view

Details

N/A
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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5 BR / 3 BA / Sleeps 10

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Chilmark - 5 bedrooms with water views 126309

Chilmark house
5 BR / 3 BA / Sleeps 10 | Quick view

Details

N/A
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Deck
  • Grill
  • Pet friendly - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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