Chilmark
https://sandpiperrental.icnd-cdn.com/images/resorts/Lucy Vincent 9-13-16.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/IMG_2188.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/Town Beach.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/Menemsha Basin 6-1-2016.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/menemsha docks.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/SandpiperRentals_.jpg
https://sandpiperrental.icnd-cdn.com/images/resorts/SandpiperRentals_-2.jpg
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!
33 properties available
Welcome to your dream retreat, a stunning home set behind a private gate on a hillside with breathtaking views of Squibnocket Pond and the beautiful South Shore of the Atlantic. Large windows fill the space with natural light, while expansive decks invite you to relax and soak up the sun. With five spacious bedrooms and five luxurious bathrooms, th
Chilmark 2073
Welcome to your dream retreat, a stunning home set behind a private gate on a hillside with breathtaking views of Squibnocket Pond and the beautiful S... Read More
Welcome to your dream retreat, a stunning home set behind a private gate on a hillside with breathtaking views of Squibnocket Pond and the beautiful S... Read More
Stunning water view property in Chilmark overlooking Quitsa Pond. Great water access with a private, shady path to Clam Point Cove. Exquisite sunsets and water views to Menemsha. Large parking area adjacent to the Pond. Spacious kitchen and dining room spills onto the large, elevated deck overlooking Quitsa Pond with additional dining and loung
Chilmark 2062
Stunning water view property in Chilmark overlooking Quitsa Pond. Great water access with a private, shady path to Clam Point Cove. Exquisite sunset... Read More
Stunning water view property in Chilmark overlooking Quitsa Pond. Great water access with a private, shady path to Clam Point Cove. Exquisite sunset... Read More
Stunning, private, four and a half acre property set high atop shared driveway in Chilmark with association tennis court, dock and water access to pond and the private section of South Beach. This house is a nature's paradise, with over four acres of trails, large, spacious yard, outdoor shower and great outdoor patio space. Enjoy wonderful summer
Chilmark 2063
Stunning, private, four and a half acre property set high atop shared driveway in Chilmark with association tennis court, dock and water access to pon... Read More
Stunning, private, four and a half acre property set high atop shared driveway in Chilmark with association tennis court, dock and water access to pon... Read More
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 includes a key/access to private Black Point Beach. The home has distant views of the Atlantic, is privately situated on over three acres of land and is light and bright with lots of windows and warm wo
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
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
Beautiful Chilmark with modern renovation located half a mile from the historical Menemsha Harbor. This reverse living home offers large open spaces and is the perfect vacation escape. The 3 bed 2 bath includes 2 Queen bedrooms that share a hall full bathroom and a main bedroom complete with a king bed and ensuite full bathroom. The upstairs open c
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
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
Charming two-bedroom cottage with one-bedroom guest house with water view just minutes into Menemsha where you can purchase lobsters fresh off the boat. The well stocked kitchen has everything you need for that lobster boil. Relax and eat on the outdoor deck and watch the sunset. Both houses, wonderfully decorated with antiques and top quality f
Chilmark 2068
Charming two-bedroom cottage with one-bedroom guest house with water view just minutes into Menemsha where you can purchase lobsters fresh off the boa... Read More
Charming two-bedroom cottage with one-bedroom guest house with water view just minutes into Menemsha where you can purchase lobsters fresh off the boa... Read More
Escape to an enchanting studio cottage up Island, where you'll find a delightful retreat waiting for you. This charming cottage boasts a cozy galley kitchen, small dining table, comfortable queen sofa bed with updated mattress, and full bathroom. This cottage has two, small screened porches to enjoy the fresh air while taking in the serene natural
Chilmark 2053
Escape to an enchanting studio cottage up Island, where you'll find a delightful retreat waiting for you. This charming cottage boasts a cozy galley k... Read More
Escape to an enchanting studio cottage up Island, where you'll find a delightful retreat waiting for you. This charming cottage boasts a cozy galley k... Read More
This up island Chilmark Cape Cod style house overlooks the South Shore barrier beach. Sprawling house and grounds provide plenty of room for family and friends.
The house centers around a large kitchen, living, dining area that spills onto the expansive deck facing the ocean. Listen to the waves break from the primary bedroom suite with a private
Chilmark 2044
This up island Chilmark Cape Cod style house overlooks the South Shore barrier beach. Sprawling house and grounds provide plenty of room for family a... Read More
This up island Chilmark Cape Cod style house overlooks the South Shore barrier beach. Sprawling house and grounds provide plenty of room for family a... Read More
A grand summer house on Martha's Vineyard where memories are made. This landmark, hilltop Victorian offers magnificent 270-degree views over meadows, Menemsha Pond and the North shore. Access to Hancock Beach with adjacent parking, as well as Menemsha pond Just moments away. Two spacious living rooms, front hall with grand staircase, dining room, s
Chilmark 2020
A grand summer house on Martha's Vineyard where memories are made. This landmark, hilltop Victorian offers magnificent 270-degree views over meadows, ... Read More
A grand summer house on Martha's Vineyard where memories are made. This landmark, hilltop Victorian offers magnificent 270-degree views over meadows, ... Read More
Wonderful two-bedroom home located up on the hill of North Abel's Hill neighborhood. Central air-conditioning. Porch for outdoor dining, wrap around deck, association access to tennis. There is stunning south shore beach access as well. The home is a just a short distance to Chilmark center, Menemsha, and Lucy Vincent beach. Enjoy a day at Lucy Vin
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
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
This comfortable Chilmark Contemporary Reverse-Style home is the quintessential Up-Island get-away. There are 4 Bedrooms spread across 3 floors offering plenty of privacy for the whole family. The Kitchen and Living Space span the top floor with deck access to enjoy the breezy summer nights. There are 2 outdoor showers with one directly off of the
Chilmark 2003
This comfortable Chilmark Contemporary Reverse-Style home is the quintessential Up-Island get-away. There are 4 Bedrooms spread across 3 floors offeri... Read More
This comfortable Chilmark Contemporary Reverse-Style home is the quintessential Up-Island get-away. There are 4 Bedrooms spread across 3 floors offeri... Read More
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 the best views the island has to offer, but is minuets to Menemsha village, with its' artisans shops, and beaches. This property includes the main house, along with a spacious guest house with a queen
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
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
Tell us what you're looking for and someone will contact you with available options.
