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Vacation Rentals in Chilmark, MA
Vacation Rentals
USA
Massachusetts (MA)
Martha's Vineyard
Chilmark Vacation Rentals
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Internet or Wifi (72)
Washer/Dryer (68)
Grill (64)
Air Conditioning (59)
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Suitability
Kid friendly (71)
Pet friendly (33)
Smoking allowed (2)
Wheelchair access (0)
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Property type
Vacation Rental House (73)
Condominium/Apartment (1)
Cabin Vacation Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (13)
Boat Available (4)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
Lucy Vincent Beach
Menemsha Hills
The Grey Barn
Great Rock Bight Preserve
Chilmark Free Public Library
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74 rentals
in Chilmark.
Classic, upscale Chilmark Captain's House and PRIVATE BEACH KEY
43 reviews
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 12
Match:
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Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
Match:
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Beautiful Chilmark - Blueberry Ridge - August!
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Chilmark two bedroom, one bath cottage with waterfront and private beach
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
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Menemsha Harborside Cottage.
2 reviews
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Private guesthouse in Peaceful Chilmark Neigborhood
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Pet-Friendly Historic Chilmark Cottage
8 reviews
Rental Home
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3 bedrooms
1 bathroom
Sleeps 5
Match:
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Chilmark pond side cottage with beach access, sweeping views 15 June - 15 Sept
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 7
Match:
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Charming Rustic Cottage
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 5
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Classic Vineyard summer cottage with private waterfront access.
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
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Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday
5 reviews
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
Match:
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Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
7 reviews
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 5
Match:
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Two Separate 3 Bed / 3 Bath Offerings - Private Beach in Chilmark, WiFi, AC
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
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Pet-Friendly Historic Chilmark House
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
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Classic Cape in ideal, Chilmark location, Pet Friendly
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Private Sanctuary in Chilmark
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 7
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Luminous rural retreat with spectacular ocean views.
19 reviews
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 10
Match:
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60 Acres of Oceanfront Property with Private Beach!
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 12
Match:
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Private Hilltop Chilmark Estate with private tennis court, gym and hot tub
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
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Peaceful Chilmark Enclave with Abel's Hill Association Beach and Tennis Courts
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 10
Match:
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Cool, Mid-Century House -- Lucy Vincent Beach and Pool!!!
12 reviews
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
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Tranquil Setting in Chilmark Off South Road
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
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Private Oceanfront Compound, 1/3 mi Private Beach, AC, Chilmark, WiFi
Rental Home
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5 bedrooms
5 bathrooms
Sleeps 10
Match:
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3 Bedroom House with Guest Cottage on 3 Acres off Middle Road
6 reviews
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 10
Match:
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Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
30 reviews
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
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Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
Match:
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Stunning Oceanfront Home in Chilmark
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 10
Match:
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Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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CHILMARK WATERFRONT WITH PRIVATE DOCK
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
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Tucked Away on Tea Lane, Chilmark
2 reviews
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 9
Match:
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Private Home in Gated Community with Private Beach!
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 3
Match:
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Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
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"Over South", Family farm house in Chilmark
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Charming Chilmark Cottage With Big Atlantic View; Private Pond And Beach
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
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PRIVATE CHILMARK HOME, 5BR,5 bath, 2 outdoor showers, AC
Rental Home
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5 bedrooms
5 bathrooms
Sleeps 12
Match:
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10 minutes walk to Lucy Vincent Beach
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
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Beautiful dog-friendly home with water view, balcony & washer/dryer
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Cozy efficiency apartment/heated pool
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
Match:
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Menemsha Pond waterfront cottage SEPT/OCT 2024 DEEP FALL DISCOUNT
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 8
Match:
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House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View.
10 reviews
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
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Spectacular Oceanfront, 4 BR/4 bath, Hottub, Private Beach, Tennis, AC, WiFi
Rental Home
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4 bedrooms
6 bathrooms
Sleeps 10
Match:
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Waterfront cottage a short boat ride or wade to ocean beach
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps
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Beautiful house on Chilmark Pond with water view, pool & access to private beach
2 reviews
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
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Chilmark Farmhouse and Barn
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Modern Luxury Waterview Home, Private Beach Access, 4 BR, 3 bath
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
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Quintessential Chilmark Retreat - Marthas Vineyard
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
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Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
Rental Home
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2 bedrooms
1 bathroom
Sleeps 3
Match:
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Cozy Sanctuary with Water Views
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 10
Match:
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Classic Modern House on its Own Point of Land with Astounding Views
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 11
Match:
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Showing results 1-50 of 74
Frequently Asked Questions about Chilmark
Do any vacation rentals in Chilmark have a pool?
Yes, here are some popular vacation rentals in Chilmark that have a pool:
Classic, upscale Chilmark Captain's House and PRIVATE BEACH KEY
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
Beautiful Chilmark - Blueberry Ridge - August!
See all vacation rentals with a pool in Chilmark on Tripadvisor
Do any vacation rentals in Chilmark have internet access?
Yes, here are some popular vacation rentals in Chilmark that have internet access:
Classic, upscale Chilmark Captain's House and PRIVATE BEACH KEY
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
Beautiful Chilmark - Blueberry Ridge - August!
See all vacation rentals in Chilmark on Tripadvisor
What are the best pet friendly rentals in Chilmark?
The best pet friendly rentals in Chilmark are:
Classic, upscale Chilmark Captain's House and PRIVATE BEACH KEY
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
Chilmark two bedroom, one bath cottage with waterfront and private beach
See all pet friendly vacation rentals in Chilmark on Tripadvisor
What are some great rentals in Chilmark that are kid friendly?
Some of the most popular kid friendly rentals in Chilmark are:
Classic, upscale Chilmark Captain's House and PRIVATE BEACH KEY
Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
Beautiful Chilmark - Blueberry Ridge - August!
See all kid friendly vacation rentals in Chilmark on Tripadvisor
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