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
Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary retreat. Lounge by the pool, dine outdoors, and sleep peacefully in one of the Thuma beds. The main floor offers open-concept living, dining and kitchen spaces with grand vaulted ceilings anchored by
Chilmark 2001
Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary ... Read More
Vacation bliss awaits in this newer four-bedroom home with a pool in Chilmark. Enjoy the quiet luxury of up-island in this sophisticated contemporary ... 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
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
A sprawling farmhouse which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. A new first floor primary suite as well as recent renovations throughout further enhance an already beautiful spot - embracing the casual, carefree feeling within the calm, private serenity of up-island. The property offers six beautifully de
Chilmark 2064
A sprawling farmhouse which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. A new first floor primary suite as well as... Read More
A sprawling farmhouse which neighbors the Blue Heron Farm in Chilmark is a found jewel with fabulous views. A new first floor primary suite as well as... 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
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
Lovely Chilmark cottage tranquilly situated at the end of Abel's Neck Road. The deck that fronts the entire length of the house affords meadow views and Menemsha Pond vistas featuring spectacular sunsets. This well-maintained single-story home boasts 4 bedrooms, two and a half bathrooms, and a wonderful open living/dining/kitchen plan. There are ca
Chilmark 2085
Lovely Chilmark cottage tranquilly situated at the end of Abel's Neck Road. The deck that fronts the entire length of the house affords meadow views a... Read More
Lovely Chilmark cottage tranquilly situated at the end of Abel's Neck Road. The deck that fronts the entire length of the house affords meadow views a... Read More
An adorable Menemsha cottage with fabulous water views! Three bedroom, two bath with single level living. Enjoy sitting out on the spacious deck with your morning coffee, a book or a glass of wine after a glorious day of exploring on the island of Martha's Vineyard. The quaint village of Menemsha is full of small quick bites, shopping, antiques, th
Chilmark 2019
An adorable Menemsha cottage with fabulous water views! Three bedroom, two bath with single level living. Enjoy sitting out on the spacious deck with ... Read More
An adorable Menemsha cottage with fabulous water views! Three bedroom, two bath with single level living. Enjoy sitting out on the spacious deck with ... Read More
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 on the page. A modern farmhouse with a sophisticated décor, a coalescence of mid-century modern, industrial and antique furnishings. Comfortable living spaces share a see-through gas fireplace, gourmet
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
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
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
Discover unparalleled luxury on 7.2 acres of secluded bliss in Chilmark, just a short distance from the other enchanting towns of Martha's Vineyard. This 4300 sq. ft. haven grants you exclusive access to the pristine Quansoo Beach, a private association beach of unparalleled beauty. Additionally, the opportunity to purchase passes for any of Chilma
Chilmark 2017
Discover unparalleled luxury on 7.2 acres of secluded bliss in Chilmark, just a short distance from the other enchanting towns of Martha's Vineyard. T... Read More
Discover unparalleled luxury on 7.2 acres of secluded bliss in Chilmark, just a short distance from the other enchanting towns of Martha's Vineyard. T... 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.
