Chilmark Vacation Rentals
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66 rentals in Chilmark.
Beautiful dog-friendly home with water view, balcony & washer/dryer
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Classic, upscale Chilmark Farmhouse and private beach
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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3 Bedroom House with Guest Cottage on 3 Acres off Middle Road
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy efficiency apartment/heated pool
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Menemsha Village - Davis Cottage - Recent Cancellations. 9/7-9/21. 20% OFF
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful Chilmark - Blueberry Ridge - August!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chilmark two bedroom, one bath cottage with waterfront and private beach
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Menemsha Harborside Cottage
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Private guesthouse in Peaceful Chilmark Neigborhood
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Oceanfront Home in Chilmark
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
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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Chilmark pondside cottage with private beach, sweeping views
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Charming Rustic Cottage
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Charming Chilmark Cottage With Big Atlantic View; Private Pond And Beach
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Secluded Guest House overlooking Menemsha Pond. Dogs welcome.
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
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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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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Quintessential Chilmark Retreat - Marthas Vineyard
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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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Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Ideal Menemsha House with Private Beach and Breathtaking Sunset Views
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Clay Cliffs in your Backyard, Private Beach in Chilmark, 3 BR, 3 bath, WiFi, AC
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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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Spectacular Newly Renovated Home in Menemsha
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Vintage 1920s House W/Beach Path & Glorious Sunset Water Views
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spacious and gracious architect designed home on 3 acres off Middle Road.
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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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Amazing Water Views in Chilmark, 4-BR, Waterfront, Key to Zak’s Beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 7
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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Light Open Vacation Home, Sweeping Waterviews, Hill Top, Private
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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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Best deal in Chilmark (Open Memorial Day weekend-Nov. 15)
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Modern Luxury Waterview Home, Private Beach Access, 4 BR, 3 bath
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Lovely Chilmark home on Abel's Hill with private beach, pond, tennis, and trails
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private Home in Gated Community with Private Beach!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
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Peaceful Chilmark Farmhouse by Menemsha Beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Classic Cape in ideal, Chilmark location, Pet Friendly RT Ferry res 9/1-9/7
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful House on Menemsha Hill - 2 min from beach!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Menemsha Pond waterfront cottage
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private Sanctuary in Chilmark
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 7
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 WATERFRONT WITH PRIVATE DOCK
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Private Hillside Home with Open Property and a Fully Equipped Kitchen
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 66
Frequently Asked Questions about Chilmark
- Yes, here are some popular vacation rentals in Chilmark that have a pool:
- Beautiful dog-friendly home with water view, balcony & washer/dryer
- Classic, upscale Chilmark Farmhouse and private beach
- Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
- Yes, here are some popular vacation rentals in Chilmark that have internet access:
- Beautiful dog-friendly home with water view, balcony & washer/dryer
- Classic, upscale Chilmark Farmhouse and private beach
- Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
- The best pet friendly rentals in Chilmark are:
- Beautiful dog-friendly home with water view, balcony & washer/dryer
- Classic, upscale Chilmark Farmhouse and private beach
- Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
- Some of the most popular kid friendly rentals in Chilmark are:
- Beautiful dog-friendly home with water view, balcony & washer/dryer
- Classic, upscale Chilmark Farmhouse and private beach
- Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
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