Updated on Jul 20, 2026
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Type
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Private vacation home
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Bedrooms
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5
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Bathrooms
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1
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House Rules
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No pets allowed
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Adults only
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Smoking is not permitted
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No events allowed
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Max Occupancy
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11
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Host Language
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English
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Property Id
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216987
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Designed by a student of the famous architect Walter Gropius, our house was built in 1949. The house is open and light, with floor to ceiling windows and sliding glass doors, a fireplace with a 50's "conversation pit" for cozying up in, perfect for an evening of charades or quiet reading. The giant dining table has room for a large family to spread out, or have a group of friends over for a long summer dinner. The multiple couches and seating areas suit a grandma reading aloud to small ones while in another area teenagers chat or grownups have cocktails on the porch, looking at the serene view of the nature preserve across the pond. There is a good layout for two families with children to share the house. It is also a romantic spot for two people to enjoy a beautiful private place.
We have lots of amusements and we are TV free. We have a fantastic collection of children's books, from picture books to favorite read-alouds and young adult books. There is a croquet set and lots of rainy day games and little kid toys. We have a modest but peaceful writers cabin/shed that can be used for quiet work time (no Wi-Fi there).
Our point of land the house sits on (see map) is 9/10ths surrounded by water, Menemsha Pond on one side and Quitsa Pond on the other. Part of the 11 acres is conserved land and the view is beautiful from anywhere. Children love exploring the mowed paths and most likely will find the hidden tree house. Chockers Point has always been occupied by sailors and you can beach a sunfish easily. It is also excellent for jumping into a kayak and exploring the ponds. We provide 2 single kayaks. We also have clamming supplies, our beach is rich with steamer clams in the summer.
This house is perfect for small children, the third generation of our family is now proving that. Children can toddle or paddle about on the private beach on Menemsha Pond, 'Short Beach' (we share it with the other houses on our short road but there is always room) where we all learned to swim. Beach passes for the restricted town ocean beaches are available for purchase from the town with your lease. The free Menemsha public beach and it's great fish markets are nearby. There is a fantastic local farmer's market in nearby West Tisbury twice a week.
Chilmark has a wonderful community center summer camp program that runs every weekday morning for children up to 12, where your kids can play sports or make glorious messes. You can sign up by the week. Retrieve your children at noon and go across the street to get a pizza for lunch from the popular Chilmark store. The Chilmark library is excellent and has a lot of kid's programs.
In the fall it is a great spot for quiet adult time. The island is more peaceful and the colors are spectacular. The weather is generally wonderful then and if it is not the wood stove is exceedingly cosy.
This is not a fancy house. It is built very simply, in a style of '50's summer camp minimalism. The comfortable furniture is a little worn, but it's classic style (Eames etc) echos the house. We have only one full and one half bath and a beautiful reconstructed outdoor shower. The house has a very warm feel that we hope you love as we do.
We no longer provide Wi-Fi. Because we are located on a peninsula, the Wi-Fi was provided via a hotspot and we were not able to guarantee the quality of the Wi-Fi for multiple simultaneous users. We have decided that because it is very simple to either use a smartphone as a Wi-Fi hotspot or bring an additional Wi-Fi hotspot as part of a standard phone plane, it is much more reliable for people who need to work remotely to provide their own Wi-Fi and that way they can monitor if other guests are sharing the Wi-Fi with them. Both Verizon and ATT get good service at Chockers Point. Please reach out if you have questions about this.
We do not rent for under 1 week, NO weekends. We give discounts for long rentals.
Keywords: Summer House, Derby, Kayaks, Dogs
Located in Chilmark, this vacation home is on the beach. Island Cove Miniature Golf and Island Cove Adventures are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Chilmark Chocolates and Fulling Mill Brook Preserve. The Grey Barn and Farm and Polly Hill Arboretum are also worth visiting. Discover the area's water adventures with kayaking and snorkeling nearby, or enjoy the great outdoors with hiking/biking trails and horse riding.
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