Chilmark MA Real Estate & Homes for Rent

WEEKLY RENTAL $13,000/WEEK. 3 bed, 3 bath + outdoor shower with chef's kitchen and top of the line appliances, this home was built in 2018. Home also has cold plunge as well as a sauna. The exquisite post & beam Allen Farm Hilltop Farmhouse perched 150 feet above Lucy Vincent Beach & the Atlantic Ocean in Chilmark has the best views on the island and provides unmatchable privacy. The 100+ acre property is surrounded by stone walls and nature. House has direct access to Lucy Vincent Beach & Chilmark Pond. Enjoy the fresh veggie garden & eggs provided by the farm, as well as the beautiful & historic farmland & pastures that have been owned by the Allen family since 1762! The 3 season screened in porch, chef's kitchen, and open layout are ideal for entertaining. Sleeps 10. 3+ bedrooms, 3 full bathrooms, + outdoor shower. The rental comes w kayaks/canoes, and views as far as the eye can see. Linens provided.

**BOOKING SUMMER 2024** Welcome to 11 Hammett Lane in Chilmark, up-island on beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. Affectionately named 'The Blueberry House' by the original owners, this 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime location off North Road next to North Tabor Farm, Great Rock Bight Preserve, Menemsha Beach, The Chilmark Store, Library and Community Center. The gorgeous grounds are dotted with wild blueberries and embraced by tall trees alive with local birds. Bright, light, and easy. Perfect for a long summer stay, fall leaf peeping, visiting family and friends and retreating artists alike. Furnished, Kitchenware provided, Sheets, Bath & Beach Towels provided,Washer/Dryer. Beach Passes can be purchased for Lucy Vincent and Squibnocket. INQUIRE FOR AVAILABILITY. Taxes,Cleaning, Security Additional.

Weekly Rental The "Grapevine" is located on a private road next door to the Beach Plum Inn, It was completely rebuilt not to long ago it has 3 generous size bedrooms all with private baths, 2 of the bedrooms are located on the second floor, 1 bedroom is located on the first floor as well as the Open concept living with a chefs Kitchen, living room ,dining area and fireplace area. Walk out the Sliding doors to your spacious deck with propane gas grill, wonderful views to Vineyard sound and Elizabeth Islands . Private Outdoor shower in the back.The lower level has an extra living room/ bedroom equipped with sofa ,chairs and a flat screened tv. Take a stroll down the Private Trail, pass by a barn with animals, walk out to a meadow and to Menemsha Beach. fully air conditioned . All the amenities you could want. You will be able to get Beach Passes to the famous Lucy Vincent Beach in Chilmark. Walk to Menemsha Beach and Village, boat rentals, fishing, Eating, swimming and so much more..

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Expansive home in North Abels Hill association with water views, private association beach and tennis. Centrally air conditioned, this family home has been well appointed with a large living room featuring fireplaces at both ends, a formal dining room, a first floor primary bedroom with en suite as well as a second floor primary bedroom with en suite. Fully equipped kitchen with a six burner gas stove, double ovens and gorgeous granite countertops. Outdoor to indoor living is easy with a stone patio and large grassy lawn overlooking the Atlantic Ocean. Come, enjoy and relax!

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Charming three bedroom cottage set on a hill overlooking a tranquil meadow just 1 & 1/2 miles to Aquinnah Cliffs. Enjoy access to both Philbin and Lobsterville beaches. There is a front and back porch with rocking chairs to take in the landscape and enjoy the breeze. This sunny property is easily accessible as well as peaceful and relaxing. Owner is working with a company to install a 5,000 BTU mini split with A/C in the living room in June but we cannot guarantee it will be done. They are putting a window A/C unit in the largest bedroom.

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! Breathtaking water views from this contemporary home located on Menemsha Pond and recently renovated with new kitchen and baths. This four bedroom retreat offers the perfect place to come during the summer months or even enjoy during the shoulder season while sitting by the fire with a warm cup of your favorite hot beverage. PLEASE TAKE NOTE!!!!!THIS IS A WEEKLY SUMMER RENTAL NOT A MONTHLY RENTAL. THE PRICE ON THIS LISTING IS A WEEkLY PRICE!!!!!!!

THIS IS A WEEKLY RENTAL PROPERTY!! This spacious two bedroom home is filled with classic Vineyard charm. Each room features spectacular views overlooking Vineyard Sound, as well as stellar sunsets in the evening. Close to Menemsha Village and public beach as well as access to Lucy Vincent and Squibnocket beaches.

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and master bedroom. Two week minimum. Owner requires interim cleaning between weeks.

THIS IS A WEEKLY SUMMER RENTAL ONLY. PRICES ARE WEEKLY NOT MONTHLY. Down a private country road, this bright and breezy post and beam home sits on a 3-acre rolling wooded parcel. With southern views of the Atlantic Ocean, it's just a short drive or bike to Philbin and Lobsterville beaches and Gay Head cliffs. This very Vineyard house offers three levels of living space, chef's kitchen, spacious dining and living rooms, a screened proch and deck. Spring, summer and fall, this inviting seaside home is a good-for-your-soul retreat.

THIS PROPERTY IS A WEEKLY RENTAL PROPERTY!! A modern summer retreat is nestled high on a knoll off North Rd in picturesque Chilmark. Here in this stunning contemporary ranch you will find the upmost in Luxury. Each room is exciting, charming and has a simplistic yet artistic style. The entire house is accented with beautiful light pine flooring that pairs perfectly with the expansive main room. On each side of the main living area are two one bedroom en suite areas that offers privacy between the two bedrooms. Each bedroom has a queen bed and a twin bed affording the possibility of sleeping six people. This home is set on a hill that provides privacy and tranquility PLEASE WASH AND DRY BEACH TOWELS PRIOR TO DEPARTURE.No pets allowed.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $12,675. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set atop a hill you will find this wonderful 4 bedroom home with distant views and a wonderful lap pool. Enjoy your days on the large deck or take a swim in the pool. This great vacation home is tastefully decorated and is located on one level with plenty of space for gatherings. The living room has a fireplace with built in seating areas overlooking the yard. Each room is decorated so nicely. You will find that this is the house you will come back to year after year. By renting this home you will have access to the private town beaches that are some of the best on the island.

THIS IS A WEEKLY SUMMER RENTAL ONLY. See web site for pricing!! Newly constructed home has open concept living area with 270 degree water views, abundant natural sunlight, central AC, high end appliances, hardwood floors, rooftop deck with seating to view gorgeous island sunsets, access to several private beaches and high speed internet wifi.

THIS IS A WEEKLY SUMMER RENTAL ONLY.!! SEE WEB SITE FOR WEEKLY PRICING. This house sits up the hill and looks toward Menemsha. It is private and protected by the trees. Visit town to watch sunsets in Menemsha, dine in one of the places to eat there or take in a day at the beach.Access to and parking for beautiful private association beach.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $10,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. This gracious Vineyard elongated Cape overlooks the Keith Farm and the Atlantic Ocean beyond. The gourmet kitchen has just been beautifully renovated and is a dream. The living areas are all decorated with charm and all have views. The separate main house, with four bedrooms, and guest house, with two bedrooms, allow for comfortable space between family and guests. The gently rolling farm land and picturesque pond welcome cows and flocks of Canada geese. This excellent location is very close to Chilmark center and a quick drive, walk or hike to Lucy Vincent beach and Menemsha.

THIS IS A WEEKLY SUMMER RENTAL ONLY. SEE WEB SITE FOR WEEKLY PRICING. Sweeping views of Squibnocket Pond, Dunes, the South Shore, Nomans Land, to sunsets over Aquinnah. A great family getaway with access to Chilmark's famed Lucy Vincent and Squibnocket Beaches as well as a private association beach in Aquinnah. Roomy and inviting, this house offers 5 five bedrooms all with views, two livingrooms, a deck with views south and to the west. Well maintained and cared for.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $4,200. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Set high on a hill in picturesque Chilmark is this absolutely wonderful 3 bedroom home with a finished walk out that has a sofa bed. Each bedroom has a window A/C unit. The grounds are beautiful. Wonderful screen porch for your morning coffee or sit in the back yard and enjoy the view. Short drive to Alleys General Store, Lucy Vincent Beach and the Chilmark Store. You have access to Lucy Vincent beach. This house accepts pets with an additional deposit of $300.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $9,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Fabulous Chilmark home offers two levels of living space. On the first floor there is a fully equipped kitchen open to the dining room, a living room with fireplace, built-ins and sliders to a deck overlooking a meadow and the most incredible water views. There is a half bath, a master suite with private bath with jacuzzi tub and a private outside shower. The lower level offers 2 bedrooms, each with it's own bathroom and a living room with wet bar and sliders that open to a patio and rolling lawn. The house also has mini-spilt air conditioning for extra hot days. Just a short distance to a private association beach. Lucy Vincent and Squibnocket Beach access too.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Just a short distance from Chilmark Store, this newly remodeled home features 3 bedrooms and 2 1/2 baths. High end finishes with a beachy island feel. The master is located on the first floor with en-suit bath. Fully equipped kitchen with a Cuisinart 14-cup programmable drip coffee maker with glass carafe. There is a coffee grinder provided in the house, too.The other two bedrooms are located on the second floor and share a full bath. There are french doors off the living room to a patio. The finishing touch a lovely deck complete with seating and grill for your cooking needs.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $6,000. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Relax and enjoy this majestic estate you will call home during your stay. This slice of paradise in the coveted Seven Gates Association gives you access to two miles of private beach just half a mile away, with tennis courts also nearby and 1000 acres of conservation land. The house is exquisitely crafted, well maintained and beautifully landscaped. Views of Harlock's pond are visible from the kitchen, living area and master bedroom. Only rents two weeks all summer.

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $5,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Water views, 3 acres and stone walls. At the end of a lane, enjoy the privacy offered by 49 acres of conservation land complete with walking trails. This house is a short distance from Lucy Vincent beach, as well as from Menemsha and Squibnocket. This spacious four bedroom, 2 bath home has an expansive rear deck that offers panoramic water views. The main level offers an open kitchen and large living room complete with fireplace. An entire wall is floor to ceiling glass with French doors opening onto a large deck. All of the rooms on this floor offer stunning views, including the Master bedroom. The first level features a large family room and three ample sized bedrooms. Black Point Beach Key included with property!!!

THIS IS A WEEKLY SUMMER RENTAL ONLY.THE WEEKLY PRICE IN AUGUST IS $8,500. PER WEEK.SEE WEB SITE FOR ADDITIONAL WEEKLY PRICING. Modern 4 bedroom home completed in 2019, in Menemsha. Located on a quiet road with waterviews from the upstairs bedrooms also offers views of the famous Menemsha sunsets from the deck. Sustainably harvested flooring features silky smooth and buttery hard wood floors from reclaimed red birch. A contemporary kitchen and clean lines throughout lead to the separate open concept dining/living room layout with sliding doors to the masterfully crafted deck. First floor main Queen bedroom and private bath with gorgeous walk in shower. Three additional bedrooms upstairs share a full bath. Powder room on the first floor and private outside shower. An extra fridge in the basement can hold anything you need for your guests.

This family-friendly, three-bedroom retreat on Lighthouse Road in Aquinnah offers all the comforts of home with stunning water views of the Vineyard Sound and the Elizabeth Islands. It is beautifully decorated and nicely furnished. The home features stylish post-and-beam architecture. The main level features cathedral ceilings, wrap-around picture windows and skylights. The main level opens out to a wrap-around deck with lovely water views. The downstairs living room features a Steinway baby grand piano. This room exits to a lower-level patio with a grill and an outdoor shower to rinse off after a day at the beach.The house offers washer/dryer, 2 bathrooms, dishwasher, as well high-speed wireless internet and cable TV. The nicely equipped kitchen is open and airy with a skylight overhead, connecting to the dining area. The home, which sits on 2.3 acres, is surrounded by the quiet, natural serenity of up-island landscapes. The master bedroom on the main level features a queen bed and

THIS IS A WEEKLY RENTAL NOT A MONTHLY!!!!Windy Knoll is a 3BR, 2Bath home located in Aquinnah on a secluded lot off State Road with 160 degree views of the Atlantic Ocean. Approximately 1 mile to Philbin Beach similar distance to Moshup Beach and Lobsterville beach. Take the bike ferry over to Menemsha and enjoy sunset on the beach. Outdoor shower with multiple shower heads to wash off the sand after a long day at the beach. Relax on the deck with the magnificent view and enjoy the breeze that fits this amazing property its name. Upstairs has open kitchen living area off deck with splitter A/C, with two bedrooms each with splitter A/C and bathroom. Downstairs has TV room with pull out couch and splitter A/C, another bedroom with splitter A/C and bathroom. Lots of space for games and puzzles. Chiminea off downstairs living area. Linens included; tenants are kindly asked to wash and dry the linens before leaving the house.

WEEKLY RENTAL $20,000/WEEK. Fully updated in 1998 1773 Allen Farm Farmhouse perched above Lucy Vincent Beach in Chilmark is one of the greatest properties Martha's Vineyard & New England. If you know about Allen Farm, then you already know how special and rare this property is. This home sleeps 10, has 5 bedrooms, 3 bathrooms, a jacuzzi, open concept chef's kitchen & dining room w two living rooms, screened in porch, outdoor shower, & master bed on main floor, 3 bedrooms on the 2nd floor & big bedroom w 3 beds on the 3rd floor. The property is surrounded by stone walls, & offers direct access to Lucy Vincent Beach, Chilmark Pond & pasture in the front yard, & farmland/pasture in your backyard w fresh organic veggie garden at your disposal, you simply will not find a better vacation home. Comes w Kayaks/Canoes. Linens Provided.