Holiday Rentals in Chilmark
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
89 rentals in Chilmark.
Classic, upscale Chilmark Farmhouse and private beach
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
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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
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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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Estate Guesthouse ~ Glorious Water Views ~ 2 Private Beaches!
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
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
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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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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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Quintessential Chilmark Retreat - Marthas Vineyard
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cool, Mid Century House -- Lots of Light!!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Classic Cape in ideal, Chilmark location, Pet Friendly
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Luminous rural retreat with spectacular ocean views.
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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Pet-Friendly Historic Chilmark Cottage
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
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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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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In Menemsha Village - Sunset House
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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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Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
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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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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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3 Bedroom House with Guest Cottage on 3 Acres off Middle Road
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
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Charming Chilmark beach house with private Abel's Hill beach access
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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Menemsha Harborside Cottage
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Chilmark Vista and Lucy Vincent Beach
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
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Airey Two Bedroom Menemsha cottage
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Quiet Home with Beach & Peek-A-Boo Ocean Views, Free WiFi, Washer/Dryer
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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
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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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Peaceful Chilmark Farmhouse by Menemsha Beach
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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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
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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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Chilmark Farmhouse with access to Hancock Beach
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful, Historic Farmhouse & Guest House on Chilmark Pond
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Gracious and Spacious Chilmark Home with a Pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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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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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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Home near the ocean with WiFi, central AC, washer/dryer, deck and firepit
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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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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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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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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Cozy efficiency apartment/heated pool
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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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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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Stunning private family home - spectacular sunsets
Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 16
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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Pet-Friendly Historic Chilmark House
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
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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10 minutes walk to Lucy Vincent Beach
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Oceanfront, 4 BR/4 bath, Hottub, Private Beach, Tennis, AC, WiFi
Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
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Showing results 1-50 of 89
Frequently Asked Questions about Chilmark
- Yes, here are some popular holiday rentals in Chilmark that have a pool:
- Gracious and Spacious Chilmark Home with a Pool
- Chilmark Farmhouse with access to Hancock Beach
- Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
- Yes, here are some popular holiday rentals in Chilmark that have internet access:
- Chilmark Farmhouse with access to Hancock Beach
- Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
- Gracious and Spacious Chilmark Home with a Pool
- Some of the most popular kid friendly rentals in Chilmark are:
- Striking 5BR/4BA Chilmark Contemporary with Views of the Sound
- Beautiful, Historic Farmhouse & Guest House on Chilmark Pond
- Vintage 1920s House W/Beach Path & Glorious Sunset Water Views