Chilmark Holiday Apartments
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71 rentals in Chilmark.
Beautiful dog-friendly home with water view, balcony & washer/dryer
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Classic, upscale Chilmark Captain's House and PRIVATE BEACH KEY
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Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
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3 Bedroom House with Guest Cottage on 3 Acres off Middle Road
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Water-view home in great location with spacious backyard, grill, kayaks, dogs OK
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Cozy efficiency apartment/heated pool
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Menemsha Village - Davis Cottage
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Beautiful Chilmark - Blueberry Ridge - August!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Menemsha Harborside Cottage.
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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
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Chilmark pond side cottage with beach access, sweeping views
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Charming Rustic Cottage
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Charming Chilmark Cottage With Big Atlantic View; Private Pond And Beach
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Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl 2 EV charger.
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In Menemsha Village - Sunset House
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Peaceful Wooded Retreat, Short Car Ride to Everything. Week is Friday to Friday
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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
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Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
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House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View.
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Two Separate 3 Bed / 3 Bath Offerings - Private Beach in Chilmark, 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
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Secluded house in the woods with deck, streamside firepit, Vincent Beach nearby
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Spectacular Newly Renovated Home in Menemsha
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Secluded mid-century home with wraparound deck, yard, grill, partial AC, & W/D
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Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views
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Vintage 1920s House W/Beach Path & Glorious Sunset Water Views
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Mid-Century Modern - All Glass House - Designed By Frank Lloyd Wright Apprentice
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Pet-Friendly Historic Chilmark House
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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
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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
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Light Open Vacation Home, Sweeping Waterviews, Hill Top, Private
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"Over South", Family farm house in Chilmark
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Best deal in Chilmark/May 15-Nov. 15
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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
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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
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Quintessential 4 BR Cape in wooded Chilmark location - Pet Friendly
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Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!
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Peaceful House on Menemsha Hill - 2 min from beach!
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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
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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
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Luminous rural retreat with spectacular ocean views.
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60 Acres of Oceanfront Property with Private Beach!
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Showing results 1-50 of 71
Frequently Asked Questions about Chilmark
- Yes, here are some popular holiday rentals in Chilmark that have a pool:
- Beautiful dog-friendly home with water view, balcony & washer/dryer
- Classic, upscale Chilmark Captain's House and PRIVATE BEACH KEY
- Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
- Yes, here are some popular holiday rentals in Chilmark that have internet access:
- Beautiful dog-friendly home with water view, balcony & washer/dryer
- Classic, upscale Chilmark Captain's House and PRIVATE BEACH KEY
- 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 Captain's House and PRIVATE BEACH KEY
- 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 Captain's House and PRIVATE BEACH KEY
- Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
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