Chilmark

Chilmark is a small, rural community with most of its land devoted to residential and agricultural use. It boasts beautiful homes set on rolling hills, rambling stone walls, grazing sheep, and one of the most beautiful of all Vineyard drives: Middle Road. The center of town is quaint and is home to the Chilmark Community Center, library and town offices, the Chilmark Store and the Chilmark Tavern where you might spot a celebrity sitting in one of the rocking chairs on the porch enjoying a slice of pizza. Heading north from the town center is the little fishing village of Menemsha, arguably the best place to watch a sunset on the Vineyard. Fishing and charter boats are tied up on the dock where you can grab the freshest prepared seafood or the catch of the day at one of the fish markets. The Homeport Restaurant overlooks the harbor and there are galleries and shops lining the road to the beach. Menemsha Beach is open to the public and is on the calm water side of the island, parking fills fast so head there early. Lucy Vincent and Squibnocket Beach are on the south or surf side of the island and are reserved for town residents or their guests/renters only. These exclusive beaches alone are popular reasons to rent a home in Chilmark! 


Properties Available 36 properties available
BR1 King En Suite with Shower Tub Combo, First FloorBR2 Queen En Suite with Shower Tub Combo, First FloorBR3 (2) Twin Beds, Lower LevelHall Bath with Shower Tub Combo, Lower LevelBR4 (2) Twin Beds, Lower LevelAdditional Sleeping: Double Bed, Lower LevelPowder Room, First Floor
Chilmark Pet Friendly
$8,800.00 - $14,000.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 9 sleeps
Chilmark 2077
This four bedroom contemporary is the perfect up-island getaway just a mile from Lucy Vincent Beach, less than 2 miles to the Chilmark Store AND it in... Read More
June 2025
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BR1 King, Lower LevelHall Bath with Shower Stall, Lower LevelBR2 Queen, Second FloorPowder Room, Second FloorBR3 (2) Twin Beds, Second FloorLaundry, Lower Level
Chilmark
$4,500.00 - $14,000.00 / per week
Beds 3 beds
Baths 1 Full, 1 Half Bath
Sleeps 6 sleeps
Chilmark 2014
Stunning views! From the moment you drive down the peaceful, semi-private driveway you sense the solitude and beauty of the surroundings. Located on e... Read More
June 2025
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BR1 King En Suite with Shower Stall, First FloorBR2 Queen, First FloorHall Bath with Shower Stall, First FloorBR3 Queen, First Floor
Chilmark
$7,000.00 - $10,000.00 / per week
Beds 3 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Chilmark 2056
Beautiful Chilmark with modern renovation located half a mile from the historical Menemsha Harbor. This reverse living home offers large open spaces a... Read More
June 2025
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1 2 3 4 5 6 $7000 7
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BR1 Queen, First FloorHall Bath with Shower Tub Combo, First FloorBR2 (2) Twin Beds, First Floor
Chilmark
$3,100.00 - $4,250.00 / per week
Beds 2 beds
Baths 1 Full Bath
Sleeps 4 sleeps
Rating 4 (1)
Chilmark 2084
A Chilmark cottage situated with privacy in a wooded area not too far from town beaches and Alley's General store. Enjoy peaceful mornings and evenin... Read More
June 2025
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Main house:R1 King En Suite with Half Bath, First FloorBR2 (2) Twin Beds, First FloorHall Bath with Shower Tub Combo, First FloorBR3 Twin Bed with Half Bath & Laundry, First FloorGuesthouse:Queen with Half Bath, First Floor
Chilmark
$7,000.00 - $9,750.00 / per week
Beds 4 beds
Baths 4 Full Bath
Sleeps 6 sleeps
Rating 5 (1)
Chilmark 2061
Some of the most beautiful sunsets await you from the deck overlooking Menemsha pond and the ocean beyond. This Menemsha home offers not only some of ... Read More
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BR1 Queen, First FloorHall Bath with Shower Tub Combo, First FloorBR2 (2) Twin Beds, First FloorGuest House: BR3 Queen and (1) Twin Bed, First Floor
Chilmark
$4,048.00 - $8,222.00 / per week
Beds 3 beds
Baths 1 Full Bath
Sleeps 7 sleeps
Chilmark 2068
Charming cottage and guest house with water view just minutes into Menemsha where you can purchase lobsters fresh off the boat. The well stocked kitc... Read More
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BR1 Queen, First FloorHall Bath with Shower Tub Combo, First FloorBR2 (2) Twin Beds, First FloorPowder Room, First FloorLaundry, Lower Level (Through Bulkhead)
Chilmark Pet Friendly
$4,000.00 - $6,000.00 / per week
Beds 2 beds
Baths 1 Full, 1 Half Bath
Sleeps 4 sleeps
Chilmark 2058
Wonderful two-bedroom home located up on the hill of North Abel's Hill neighborhood. Central air-conditioning. Porch for outdoor dining, wrap around d... Read More
June 2025
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1 2 3 4 5 6 $5000 7
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BR1 Queen, First FloorHall bath, First FloorBR2 King, Second FloorBR3 Twin and Chair Bed, Second floorBR4 (1) Twin and Bunk Beds, Second FloorHall bath, Second Floor
Chilmark
$3,500.00 - $6,500.00 / per week
Beds 4 beds
Baths 2 Full Bath
Sleeps 8 sleeps
Rating 5 (2)
Chilmark 2079
Lovely Chilmark home located on the North Shore tucked into a spacious wooded lot. This home offers great social space with a dining area off of the ... Read More
June 2025
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1 2 3 4 5 6 $3500 7
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    1 2 3 4 $5500 5
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BR1 Queen and Twin Bed En Suite with Shower Tub Combo, First FloorBR2 Queen and Twin Bed, First FloorHall bath with Shower Stall, First Floor
Hot HOT 11
Chilmark
$2,800.00 - $3,700.00 / per week
Beds 2 beds
Baths 2 Full Bath
Sleeps 6 sleeps
Rating 5 (1)
Chilmark 2011
Escape to the tranquil town of Chilmark and enjoy the best of Martha's Vineyard with this charming single-level home. With a post-and-beam design, thi... Read More
June 2025
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Main house:BR1 Queen En Suite with Shower, First FloorBR2 King En Suite with Shower Stall and Tub, Second FloorBR3 Queen En Suite with Shower, Second FloorBR4 Queen En Suite with Shower, Second FloorBR5 Queen En Suite with Shower, Second FloorGuesthouse barn:BR6 Queen, Second FloorHall Bath Shower Stall, Second Floor
Chilmark Pet Friendly
$38,000.00 / per week
Beds 6 beds
Baths 6 Full, 1 Half Bath
Sleeps 12 sleeps
Chilmark 2010
Just a short distance down a charming up-island road, you will find this six bedroom estate, perfectly placed within it's surroundings, as if drawn o... Read More
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BR1 King En Suite with Shower Stall and Tub, First FloorBR2 Queen En Suite with Shower Stall, Second FloorBR3 Queen, Second FloorHall Bath with Shower Tub Combo, Second FloorBR4 Queen, Second FloorPowder Room, First Floor
Chilmark Pet Friendly
$15,000.00 - $20,000.00 / per week
Beds 4 beds
Baths 3 Full, 1 Half Bath
Sleeps 8 sleeps
Chilmark 2001
Vacation bliss awaits in this brand new four bedroom home with a pool in Chilmark. Enjoy the quiet luxury of Up-Island in this sophisticated contempor... Read More
June 2025
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1 2 3 4 5 6 $15000 7
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    1 2 3 4 $20000 5
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BR1 King with Half Bath, Second FloorBR2 (2) Twin Beds, Second FloorHall Bath with Shower Stall, First FloorDouble Size Futon, Den First Floor
Chilmark Pet Friendly
$2,500.00 - $3,500.00 / per week
Beds 2 beds
Baths 1 Full, 1 Half Bath
Sleeps 5 sleeps
Chilmark 2054
LOCATION LOCATION LOCATION! Embrace the charm of this charming 1950's cottage nestled in a prime up-island location, offering convenient access to nu... Read More
June 2025
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1 2 3 4 5 6 $3000 7
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