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!
32 properties available
Discover the charm of this bright and airy single-level, four-bedroom home in Chilmark, complete with a private spa pool (4 feet deep) that's perfect for kids and fitness enthusiasts. The house is fully equipped with mini-split air conditioning and heating units throughout. It features spacious areas for gatherings, as well as cozy spots for enjoyi
Chilmark 2008
Discover the charm of this bright and airy single-level, four-bedroom home in Chilmark, complete with a private spa pool (4 feet deep) that's perfect ... Read More
Discover the charm of this bright and airy single-level, four-bedroom home in Chilmark, complete with a private spa pool (4 feet deep) that's perfect ... 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
Lovely Chilmark home located on the North Shore tucked into a lush wooded lot. This home offers great entertaining space with a dining area off of the updated kitchen and slider out to an upper deck with tree top views. Spacious living room to sprawl out with a large sectional sofa, perfect for relaxing after a day at one of the up-island beaches.
Chilmark 2079
Lovely Chilmark home located on the North Shore tucked into a lush wooded lot. This home offers great entertaining space with a dining area off of the... Read More
Lovely Chilmark home located on the North Shore tucked into a lush wooded lot. This home offers great entertaining space with a dining area off of the... Read More
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This Martha's Vineyard rental property offers dock, mooring along with access to small beach area just down the path on Clam Point Cove. Fully renovated in 2022 with stunning views from almost every room. Enj
Chilmark 2021
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This Mart... Read More
Chilmark waterfront rental home with a dock located on Quitsa Pond with views across Quitsa and Menemsha ponds out to the Elizabeth Islands. This Mart... Read More
Nestled in a stunning spot on Upper Chilmark Pond, this charming three-bedroom beach house offers wonderful access to both the tranquil pond and a private ocean beach just across the way. Imagine spending sunny days at Lucy Vincent Beach, only minutes down the shore! Tucked away at the end of a peaceful 1/4-mile dirt road, this property is convenie
Chilmark 2022
Nestled in a stunning spot on Upper Chilmark Pond, this charming three-bedroom beach house offers wonderful access to both the tranquil pond and a pri... Read More
Nestled in a stunning spot on Upper Chilmark Pond, this charming three-bedroom beach house offers wonderful access to both the tranquil pond and a pri... Read More
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cottage has 2 bedrooms on the first floor and 2 on the second floor. Enjoy the expansive deck along the entire back of the house and dine al-fresco. The open area dining, living and kitchen spaces are the
Chilmark 2002
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cotta... Read More
Located in an exclusive Chilmark neighborhood, this home offers privacy and breathtaking views of the North Shore. This well-appointed 4 bedroom cotta... Read More
Spectacular Water View Retreat in Prospect Hill. Envision yourself vacationing in this stunning five-bedroom home located in the desirable Prospect Hill location. Enjoy breathtaking water views from nearly every room and an ideal layout designed for both comfort and connection.
The main level features an open-concept kitchen, dining, and living are
.jpg)
Chilmark 2050
Spectacular Water View Retreat in Prospect Hill. Envision yourself vacationing in this stunning five-bedroom home located in the desirable Prospect Hi... Read More
Spectacular Water View Retreat in Prospect Hill. Envision yourself vacationing in this stunning five-bedroom home located in the desirable Prospect Hi... 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
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, this home exudes unique character, while the open floor plan creates a light and inviting atmosphere. The fully equipped kitchen, dining area, and living area provide all the comforts of home. There are
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
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
LOCATION LOCATION LOCATION!
Embrace the charm of this charming 1950's cottage nestled in a prime up-island location, offering convenient access to numerous private Chilmark beaches with town permits. The open kitchen boasts new granite countertops and refinished cabinets, seamlessly connecting to the inviting living room. Additional storage is ava
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
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
Delightful Cape style guesthouse situated on the grounds of a hilltop Chilmark estate. (The estate's main house is rented separately and may be occupied.) Magnificent views over Menemsha Pond. Access to Hancock Beach with adjacent parking and Menemsha Pond just a few short moments away. First floor has an open kitchen, dining and living room with f
Chilmark 2025
Delightful Cape style guesthouse situated on the grounds of a hilltop Chilmark estate. (The estate's main house is rented separately and may be occupi... Read More
Delightful Cape style guesthouse situated on the grounds of a hilltop Chilmark estate. (The estate's main house is rented separately and may be occupi... 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
Tell us what you're looking for and someone will contact you with available options.
