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Holiday Rentals in Chilmark

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43 rentals in Chilmark.
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Classic,upscale Chilmark Farmhouse and private beach

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Newly Renovated Home in Menemsha

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Classic Cape in ideal, Chilmark location.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quintessential Chilmark Retreat With Water Views In Martha's Vineyard

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luminous rural retreat with spectacular ocean views.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Ideal Menemsha House with Private Beach and Breathtaking Sunset Views

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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comfortable ranch house overlooking Menemsha Bight

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Fully Appointed Water View House Ten Minutes Walk from Beach

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Iconic mid-century home with gorgeous ocean views, private pool and decks!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Pet-Friendly Historic Chilmark Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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In Menemsha Village - Sunset House

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Pet-Friendly Historic Chilmark House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Tucked Away on Tea Lane, Chilmark

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Chilmark home with water views and key to Black Point Beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful house on Chilmark Pond with water view, pool & access to private beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Airey Two Bedroom Menemsha cottage

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Chilmark Vista and Lucy Vincent Beach

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Chilmark House w/Sunroom on Martha's Vineyard

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Menemsha Harborside Cottage - STEAMSHIP reservations available for open Aug. wks

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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'Over South', Family farm house in Chilmark

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quiet home with beach & peek-a-boo ocean views!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful, historic farmhouse on Chilmark Pond

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Secluded mid-century home w/ large deck, yard & fireplace

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Striking 5BR/4BA Chilmark Contemporary with Views of the Sound

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Chilmark Farmhouse with access to Hancock Beach

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Family friendly beach house sleeps 12

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Spectacular Chilmark Hilltop Ocean View

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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CLASSIC VINEYARD FISHING VILLAGE VIEWS FROM THIS QUINTESSENTIAL COTTAGE

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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CHARMING HOME W/VIEWS OF VINEYARD SOUND & ELIZABETH ISLANDS

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spring Point Cottage With Gorgeous Sunsets Overlooking Vineyard Sound

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming Chilmark Cottage With Big Atlantic View; Private Pond And Beach

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Gracious and Spacious Chilmark Home with a Pool

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Estate guesthouse, glorious water view, & 2 private beaches!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Private oceanfront compound , 1/3 mi Private Beach, AC, Chilmark, WiFi

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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CHARMING COUNTRY HOME IN CHILMARK

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Secluded Property with Vineyard Sound Views and Private Beach

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beautiful Chilmark Farmhouse W/ Private South Shore Beach and Outdoor Pool

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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Light and airy modern holiday cottage with access to private beach

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private Chilmark beach on The Cliffs in your backyard, 3 BR, 3 bath, WiFi, AC

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Secluded 2-Acre Hideaway | Fireplace, Wraparound Deck | Near Trails & Beaches

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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