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Chilmark Vacation Rentals

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0+ rooms, 2+ guests
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$1,000+
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60 rentals in Chilmark.
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SPACIOUS AND COMFORTABLE CHILMARK CAPE WITH CENTRAL AIR CONDITIONING
4 bedrooms
2 bathrooms
Sleeps 8
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CHARMING COUNTRY HOME IN CHILMARK
4 bedrooms
2 bathrooms
Sleeps 8
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ARCHITECTURAL AWARD WINNING HOME WITH PANORAMIC VIEWS OF THE VINEYARD SOUND
6 bedrooms
4 bathrooms
Sleeps 10
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CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE
2 bedrooms
1 bathroom
Sleeps 4
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CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS
4 bedrooms
2 bathrooms
Sleeps 8
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Chilmark Vacation Home with Lovely Views and Pool
6 bedrooms
4 bathrooms
Sleeps 12
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4 Bedroom on 5 Acres of Woodlands with Fresh Eggs and Chickens
4 bedrooms
3 bathrooms
Sleeps 8
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Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
5 bedrooms
4 bathrooms
Sleeps 12
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Spectacular Home with Waterviews of Vineyard Sound and Elizabeth Islands
4 bedrooms
3 bathrooms
Sleeps 8
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BRESP - Waterview, Association Beach
6 bedrooms
4 bathrooms
Sleeps 10
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LEWID - Menemsha Waterfront, Magnificent Views and Private Location, WiFi
3 bedrooms
2 bathrooms
Sleeps 6
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LEWDG - Waterfront, Waterview, Walk to Beach, Hi Speed Internet, WiFi
4 bedrooms
2 bathrooms
Sleeps 6
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BERNJ - Menemsha Sea Coast Cottage, Gorgeous Waterviews, Walk to Menemsha Beach,
5 bedrooms
3 bathrooms
Sleeps 8
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HORNP - Squibnocket Farm Waterfront, Private Beach,
4 bedrooms
2 bathrooms
Sleeps 9
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SPANM - Sweet Chilmark Cottage, Spacious Screened Porch and Deck Area, Private L
3 bedrooms
3 bathrooms
Sleeps 6
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GIBBT - Large Deck, Wifi, A/C, Conveniently Located in One of The Most Beautifu
4 bedrooms
2 bathrooms
Sleeps 8
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ROSSR - Chilmark, Waterview, Private Pool
4 bedrooms
3 bathrooms
Sleeps 8
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LORUJ - Spacious Ocean View Home, Private Association Beach - South Shore - Inq
4 bedrooms
3 bathrooms
Sleeps 8
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HERGT - Luxury Retreat Chilmark, Key to Quansoo Private Association Beach, Set o
4 bedrooms
3 bathrooms
Sleeps 8
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MCAUM - Heron's Nest, Thoughtful Architectual Design set Amidst an Estate Proper
4 bedrooms
3 bathrooms
Sleeps 7
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Gracious and Spacious Chilmark Home with a Pool
4 bedrooms
3 bathrooms
Sleeps 8
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Spectacular Chilmark Hilltop Ocean View
5 bedrooms
2 bathrooms
Sleeps 9
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MEINW - Wade's Cove Waterfront Luxury Residence, Key to Private Hancock Beach,
4 bedrooms
4 bathrooms
Sleeps 8
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NOBLM - Distinctive Luxury Summer Retreat, Private Tennis Courts, Private Associ
5 bedrooms
4 bathrooms
Sleeps 9
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Family friendly beach house sleeps 12
5 bedrooms
4 bathrooms
Sleeps 12
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Waterfront cottage a short wade to ocean beach
4 bedrooms
3 bathrooms
Sleeps 10
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Pet-Friendly Historic Chilmark House
4 bedrooms
3 bathrooms
Sleeps 10
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Vintage 1920s House W/Beach Path & Glorious Sunset Water Views
3 bedrooms
3 bathrooms
Sleeps 8
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Luminous rural retreat with spectacular ocean views.
5 bedrooms
3 bathrooms
Sleeps 10
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Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
5 bedrooms
4 bathrooms
Sleeps 14
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Fully Appointed Water View House Ten Minutes Walk from Beach
4 bedrooms
3 bathrooms
Sleeps 10
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Chilmark Cottage
3 bedrooms
2 bathrooms
Sleeps 6
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Cool, Mid Century House -- Lots of Light!!
4 bedrooms
4 bathrooms
Sleeps 8
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MEINT - Stately Historic Chilmark Home, All Newly updated to Luxury Standards, P
5 bedrooms
3 bathrooms
Sleeps 10
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FERRN - Summer in Chilmark, Private Location, Large Deck w Outdoor Dining Area,
3 bedrooms
2 bathrooms
Sleeps 6
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BLASD - A Gem in Chilmark, Impeccably Maintained Home, Multiple Decks and Patio
4 bedrooms
4 bathrooms
Sleeps 8
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Luxury Expanded Cape on Wade's Cove & Key to Hancock Beach
4 bedrooms
4 bathrooms
Sleeps 8
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Chilmark Farmhouse with access to Hancock Beach
5 bedrooms
3 bathrooms
Sleeps 10
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Beautiful, historic farmhouse on Chilmark Pond
4 bedrooms
2 bathrooms
Sleeps 6
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Oceanfront cottage w/elevated deck & shared gym-on Menemsha Beach
4 bedrooms
2 bathrooms
Sleeps 6
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1 other traveler has booked this property
Oceanfront cottage w/elevated deck & shared gym-on Menemsha Beach
4 bedrooms
2 bathrooms
Sleeps 6
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Iconic mid-century home with gorgeous ocean views, private pool and decks!
4 bedrooms
2 bathrooms
Sleeps 8
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Oceanfront home w/deck, amazing sunset views & beach access-dogs OK
4 bedrooms
2 bathrooms
Sleeps 8
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Classic,upscale Chilmark Farmhouse and private beach
4 bedrooms
3 bathrooms
Sleeps 12
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Tucked Away on Tea Lane, Chilmark
4 bedrooms
3 bathrooms
Sleeps 9
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Beautiful house on Chilmark Pond with water view, pool & access to private beach
4 bedrooms
2 bathrooms
Sleeps 8
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Contemporary Cottage with Breathtaking Views
2 bedrooms
3 bathrooms
Sleeps 5
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Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
3 bedrooms
2 bathrooms
Sleeps 8
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Charming Chilmark beach house with private Abel's Hill beach access
5 bedrooms
4 bathrooms
Sleeps 10
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Ideal Menemsha House with Private Beach and Breathtaking Sunset Views
3 bedrooms
3 bathrooms
Sleeps 8
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