Home Vacation Rentals By Owner In Chilmark, MA

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Private Vacation Home

Peaceful House on Menemsha Hill - 2 min from beach!

Chilmark, Massachusetts, United States

A brand new listing! You are very welcome to this peaceful, quiet and private house in Menemsha village, just minutes from the public beach, harbor, restaurants, shops and galleries. The location doesn’t get any better, as you have the privacy by being up a small hill and away from the hustle and bustle, but you are within walking distance to Menemsha for all your needs. Menemsha is famous for beautiful and picturesque sunsets over the ocean.brbrThe house comfortably sleeps 8 adults and is perfect for a getaway with your family, partner or friends to enjoy the beauty and peacefulness of the authentic Martha’s Vineyard. The bedrooms are comfortable and clean, with two queen size and four twin beds in the house. Please note air conditioning is only available in the two queen bedrooms. brbrThe kitchen is fully equipped with a dishwasher, microwave, brand new oven/stove, refrigerator, outdoor charcoal grill and more. We recommend picking up freshly caught seafood at Larsen’s Fish Market and cooking a feast! The dining room is bright and sunny, and the perfect place to start off your morning over breakfast. brbrYou can relax with a book on the back porch, which gets both sunshine and shade throughout the day. After a trip to the beach, you can rinse off in the outdoor shower. For a cozy night in, the house offers free Wifi and cable TV. brbrThe house is within walking distance from several restaurants and cafes, both casual and high end, fish markets, an ice cream shop, several retail shops, art galleries and antique stores. The house is within a 5 minute drive from the general store, public library, the Chilmark Tavern, the community center, and several gorgeous sandy beaches. The Menemsha beach is open to the public, but Lucy Vincent Beach and Squibnocket Beach require a sticker for entry, available for purchase online (https://www.chilmarkma.gov/beach-committee/pages/beach-information). brbrThere are plenty of activities for you, such as kayaking, charter boat fishing, biking (there is a bike ferry that takes you to Aquinnah), relaxing at the beach, and more! The Gay Head Cliffs in Aquinnah are approximately 15 minutes away, and the town of Edgartown, Vineyard Haven and Oak Bluffs are approximately 30 minutes away.brbrIt is approximately a 30 minute drive from the ferries, and the house is also accessible by the public bus service if you don’t have a car. This is the place for you if you are looking for privacy, comfort and a quaint experience on Martha’s Vineyard! brbrWe are available to answer any questions you may have and will ensure that you have the most relaxing stay possible! We look forward to hearing from you.
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Bath 3

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Exceptional(1)

$8413.53

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Private Vacation Home

Private Oceanfront Compound, 1/3 mi Private Beach, AC, Chilmark, WiFi

Chilmark, Massachusetts, United States

This private Chilmark compound has breathtaking views out to the Atlantic Ocean and 1/3 mile of private beach in your backyard. It sits on 19+ acres on the Wequobsque Cliffs providing a secluded and dramatic setting that is incomparable on the island, or the East Coast. Your family, friends and guests can enjoy three separate structures: the Upper house has expansive Atlantic views with 2 bedrooms, 2 baths, living room, dining room, full kitchen, covered deck and large lawn overlooking the ocean and an outdoor shower. Private tennis court available. The Lower House has two bedrooms, two baths, living room, dining area, full kitchen, decks, dining patio and another outdoor shower. A separate building has a one bedroom apartment with a private bath and an outdoor shower to round out this magnificent property. There is also a brand new private hard court tennis court a short walk away from the home.brThese are the original cabins that were built in 1948 & 1951. They are renovated and upgraded with modern amenities, but the classic and rustic charm exudes throughout, giving you the Best that Martha's Vineyard has to offer-with one of the Best, arguably THE BEST, beach in the world in your backyard... Houses can be rented together or individually. brbrRates are subject to change. Contact manager for details. brbr
Bed 5

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Bath 5

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Exceptional(11)

$1082.56

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Private Vacation Home

Walk to Beach, Kayak from Backyard Dock, Ocean & Squibnocket Pond Views

Chilmark, Massachusetts, United States

Enjoy spectacular panoramic views of the ocean, dunes, beach and Squibnocket Pond. brbrPerfect for a family that is looking for a 4-minute walk to the beach and kayak right from the backyard dock. This 4 bedroom, 2 1/2 bath home, sleeps 8, has an open living area that brings the stunning vistas inside, features gorgeous water views of the beach that you can walk to from every room, and includes keyed access to a private beach right down the road. We installed AC in September 2024 to make your stay even more comfortable. The dining area and master bedroom open onto the spacious deck. The fully equipped kitchen faces the ocean and is adjacent to the dining area, which has seating for 8. brbrThe indoor and outdoor areas are wonderful for entertaining or just relaxing in a magnificent, yet peaceful setting. Spacious yard for games and running around when you get back from the beach or town. Once you've experienced the breathtaking water views and sunsets from our 3-acre property, you'll want to come back year after year.brbrUnique beach options include access to:br• Squibnocket Beach (just a 4-minute walk)br• Our association's private beach at Zack's Cliff (8 minutes by car, key to gate provided)br• Chilmark's renowned Lucy Vincent Beach (7 minutes by car)brbrSquinocket Pond access:br• Right in our backyard you have access to Squibnocket pondbr• Three kayaks (two singles and a tandem), canoe and rowboatbr• Paddles/oars, lifejackets, cushions, and gear are available in our paddle house stepsbrbrThe brand-new dock on Squibnocket Pond is just steps from the house and has three kayaks (two singles and a tandem), a canoe, and a rowboat for a brief paddle or more extensive exploration on the Pond. Paddles/oars, life jackets, cushions, and gear are available in the boat house close to the dock. Walk or run the neighborhood country lanes past stone walls, meadows and picturesque Vineyard homes, or follow the path to a private association dock on Quitsa Pond. The natural setting provides a wonderful opportunity to view more than 40 species of birds, including a swan family, ospreys, egrets and herons, as well as other abundant wildlife. brbrSleeping options:br• Master bedroom with queen bed and ensuite bathbr• Queen bedroom with beach and pond viewsbr• Two bedrooms with two twin bedsbrbrThe master bedroom has its own stunning views, a queen bed, private bath, and sliding glass door to the deck. The other three bedrooms are on the other side of the open living area and all have ocean views (one queen and two with two twins). A full bath and 1/2 bath are easily accessible from these three rooms. While this family home is the perfect place to unplug, our high speed Wi-Fi makes remote work or finding a recipe to go with the fish you picked up from Menemsha painless. The walkout basement has full washer and dryer to make laundry easy during your stay. Plus, we have plenty of room for rainy day activities. At the end of the day, there are tons of games for you to play or lounge on two large couches to watch a movie with a Roku TV and HDMI.brbrAdded Bonus:br• Private Association Dock on Quista Pondbr o Access to Menemsha Pondbr• Private Keyed Beach Access at Zacks Cliffsbr o Few miles down the road in Acquinnah brbr
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Bath 3

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$20106.0

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Private Vacation Home

Paradise in Chilmark, Very Private Modern Home with Heated Pool & Ocean Views

Chilmark, Massachusetts, United States

Welcome to your summer sanctuary in Chilmark! Nestled on the serene shores of Martha's Vineyard, this newly constructed, modern 4-bedroom, 5.5-bathroom home offers a perfect blend of luxury, comfort, and captivating ocean views.brbrAs you step inside, you'll immediately be drawn to the expansive vistas of the Atlantic Ocean that greet you from nearly every room. Whether you're preparing a gourmet meal in the fully equipped kitchen, unwinding in the open living area, or waking up in any of the four ensuite bedrooms, the stunning ocean panorama is never far from sight.brbrEach of the four spacious bedrooms provides a private retreat, complete with its own bathroom, ensuring that everyone in your party enjoys the utmost comfort and convenience.brbrFor entertainment and relaxation, head downstairs to the media and gaming room, where you can immerse yourself in your favorite movies, games, or sporting events with surround sound. It's the perfect space to gather with family and friends for unforgettable evenings.brbrThis Chilmark home is more than just a vacation rental; it's an experience of coastal luxury and tranquility. Additionally, it's a smart home, allowing you to control lighting, temperature, and security with ease.brbrFurthermore, for your comfort and convenience, each room is equipped with blackout and privacy shades, ensuring that you can enjoy a restful night's sleep or simply relax in private whenever you desire.brbrOutside, your summer oasis awaits. Dive into the heated pool for a refreshing swim, soak up the sun on the expansive deck, or dine al fresco while the sun sets over the water, painting the sky in vibrant hues.brbrWhether you're seeking a family getaway, a reunion with friends, or a romantic escape, this property offers everything you need for an unforgettable summer retreat. Book now to secure your slice of Martha's Vineyard paradise.
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Bath 6

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$5644.84

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Private Vacation Home

Modern Luxury Waterview Home, Private Beach Access, 4 BR, 3 bath

Chilmark, Massachusetts, United States

*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR ANY STAYS LESS THAN 7 NIGHTS, THE NIGHTLY PRICE WILL INCREASE. PLEASE SEND THE PROPERTY MANAGER THE NUMBER OF NIGHTS YOU WOULD LIKE TO STAY AND THE NUMBER OF GUESTS, AND WE WILL SEND YOU AN UPDATED PRICE.brbrThis recently renovated & tastefully decorated modern home has beautiful views of the Atlantic ocean. Located on a private road in Chilmark, you will get to experience Martha's Vineyard in the best way possible. With private beach access just a short kayak ride across the pond, you and your friends or family will have a vacation that will not be forgotten. Kayaks are provided for your convenience.brbrThe home has 4 bedrooms and 3 bathrooms, and a fantastic TV/Movie room in the basement. All bed linens and towels are provided. The kitchen is stocked with state of the art equipment, and everything you need to cook a gourmet meal.brbrIn the backyard is a brand new Lynx grill and large area to prepare food and enjoy a barbeque with your family or friends, all while getting amazing views of the sunrise or sunset.brbrJust a short ride away is the Chilmark General Store for grocer needs, and grocery delivery services are available upon request as it will be hard to want to leave this home to go down island to stock up!brbrRATES ARE SUBJECT TO CHANGE, PLEASE CONTACT THE PROPERTY MANAGER.
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Bath 3

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$400.26

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Private Vacation Home

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

Chilmark, Massachusetts, United States

Petite Guest house is private with its own driveway, yard, and easy walk to Menemsha Pond. Amazing location; walk to Menemsha harbor, beach, Galley restaurant & ice cream, fish markets. Views of Pond, Vineyard sound, Aquinnah. 2 bedrooms, galley kitchen, living room wrapped in sliding glass doors out to deck. Beach pass to Lucy Vincent & Squibnocket avail. Well behaved dogs welcome, streaming TV, Wifi, A/C, heat, laundry + level-2 EV charger. Outdoor furniture included upholstered couch with small table, lounge chairs with giant umbrella. Enjoy Weber gas BBQ. Close to Chilmark Store, Chilmark Community Center. Nestled in nature with a small lily pond onsite & ideal for disconnecting. .4 miles (7 mins) walk to Pond boat launch - great for paddle boarding or fishing. Close to Menemsha Inn & Beach Plum Inn. Great dirt roads for running or walking. Loads of hiking trails nearby. Enjoy incredible light + sunsets from the deck.brbrRecently renovated with reclaimed barn door, translucent panels, new kitchen +bath. Simple Menemsha living with amenities. This cozy home is ideal for a single person, couple, or 3 close friends. A previous guest have compared it to a small houseboat as it's cozy inside. Enjoy outdoor shower, professionally manicured grounds, and bubbling brook next to house to add to chill ambiance. Kitchen has all the modern amenities, microwave, dishwasher and is fully stocked.brbrNOTE - Our Main house just across a gentle stream via bridge is double the size of this home and may be rented together (if both available). Search VRBO # 2604149.brbr2026 bookings open October 2025. Reach out if interested.
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Exceptional(28)

$508.24

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Private Vacation Home

Vintage 1920s House W/Beach Path & Glorious Sunset Water Views

Chilmark, Massachusetts, United States

*** Please make an inquiry before booking. ***brbrThis quintessential Up-Island 1920s summer house has panoramic water sunsets thanks to its hillside position overlooking the Vineyard Sound. (An East Coast novelty to look west over water.) The view spans the Menemsha Harbor, Menemsha Bight, Gay Head Lighthouse in Aquinnah, Elizabeth Islands, and, on clear days, all the way past Buzzards Bay to the mainland.brbrDay or night it doesn't get any more Vineyard than taking in the breathtaking views from the tranquil deck. The sun's final dunk into the sea is sometimes heralded—depending on the direction of the breezes—by the faint sound of applause up from Menemsha Beach picnickers who see a slightly earlier sunset from their lower vantage point a half mile away.brbrThe house has three bedrooms—two upstairs and one downstairs—plus a queen sleeper sofa in the living room, and a small loft which overlooks the living room. brbrThe house is full of light and air with a cathedral ceiling and many windows, plus the original, working stone and brick fireplace opens on two sides to the living room and the kitchen. There are two bathrooms, and a bathtub downstairs and an outside shower. There is a also a side deck with a shaded hammock.brbrModern conveniences include wireless highspeed Internet, iTunes wireless audio, flat screen TV with DVD and DirecTV satellite, linens, washer/dryer, and dishwasher.brbrThe house has been in our family for more than forty years, and our grandparents first stayed as renters in the early 1940s. In one family story, our grandmother reported a sighting of a possible German submarine one night to the Coast Guard station, only to be told drily by the dutyman that she had correctly decoded the (then) three-whites-a-red signal of the Gay Head Lighthouse. They named the house Menucha, as a biblical reference to rest and tranquility that plays on the village's Wampanoag name of Menemsha. As an umpire of the Sunday softball game, our grandfather was also famous for his idiosyncratic strike zone.brbrHillside walking path to Vineyard Sound beach and Menemsha harbor, or take house bikes to Menemsha dock, Chilmark and Lucy Vincent ocean beach.brbrKeywords: house, summer camp, beach path, Menemsha, Chilmark, Upisland, Vineyard Sound, Menemsha Bight, Menemsha harbor, Menemsha jetty, Up Island, sunset views, beach pass, Lucy Vincent, Squibnocket, Gay Head Lighthouse, sunset
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Bath 3

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$5685.53

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Private Vacation Home

Stunning Oceanfront Home in Chilmark

Chilmark, Massachusetts, United States

*PLEASE NOTE: THE PRICES YOU CURRENTLY SEE ON THE WEBSITE ARE THE PRICES FOR 7 NIGHTS OR MORE THAN 7 NIGHT STAYS. FOR ANY STAYS LESS THAN 7 NIGHTS, THE NIGHTLY PRICE WILL INCREASE. PLEASE SEND THE PROPERTY MANAGER THE NUMBER OF NIGHTS YOU WOULD LIKE TO STAY AND THE NUMBER OF GUESTS, AND WE WILL SEND YOU AN UPDATED PRICE.brbrPerched on a bluff on the south shore of Chilmark (MV), Clethra (means summer sweet) is an original 1929 Vineyard cottage with a stunning water-front location that offers unmatched 270 degree views. To the left is a long crescent beach below the Wequobsque Cliffs that curves down to Lucy Vincent beach, and to the right is Stonewall and Squibnocket beaches. Stonewall Beach is a private beach assoc. You can walk five minutes or drive two minutes to beach parking. Beach access is limited to those who live or rent on the road.brbrClethra offers the best of low-key but active beach living. Paddle, surf, boogie board, fish, swim or lounge at the beach. Or drive 5 mins to boat launch and put in your kayak, paddle, sail boat and explore Nashaquitsa and Menemsha ponds and make your way to the fishing village of Menemsha where you can eat lobster rolls or slurp oysters in the rough by the docks. Up Island of Martha's Vineyard is the place to be away from the crowds of down island, explore farmers markets, galleries, farm stands, Aquinnah cliffs and lighthouse and the other glorious beaches that require stickers. Stonewall Beach assess is part of the rental.
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$3927.52

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Private Vacation Home

Two Separate 3 Bed / 3 Bath Offerings - Private Beach in Chilmark, WiFi, AC

Chilmark, Massachusetts, United States

Two rental opportunities are being offered within this one listing:brThe Upper House & Studio ApartmentbrThe Lower House & Studio ApartmentbrbrThe Upper House, Lower House and Studio Apartment are part of this unequaled compound. Sitting on 19 acres and boasting a clay carved staircase down to 1/3 mile private beach, just a few minutes from your door.brbrThe Studio Apartment consists of a studio apartment with a queen bed, full bathroom, kitchenette and small living area. There is an outdoor shower on the side of the apartment. Comfortable outdoor furniture for relaxing in your side yard. brbrAcross the pebble driveway sits the Lower House consisting of the Lower Main House & Detached Master Bedroom with a King size bed, large TV, private bathroom and urinal, a very large closet with small refrigerator. A large outdoor shower and beautiful deck complete this suite. Across the deck is the Lower Main House consisting of guest bedroom with a queen bed, full bathroom, kitchen, dining room, spacious living room, laundry room, plus outdoor dining area.brbrTraveling up the pebble driveway brings you to a separate parking area for the Upper House. The Upper House has stunning views of the Atlantic Ocean and consists of two bedrooms, two full bathrooms, a living room area, and a full kitchen. One bedroom is a master ensuite bedroom with king bed and beautiful bathroom. Wake up to an unobstructed view of the Atlantic Ocean. The guest bedroom has two twin beds and a private full bathroom located directly off the bedroom. The living area with ocean views and full kitchen with small dining area complete the Upper House.brbrThere is plenty of parking and a few minute walk to the clay carved staircase down the Wequobsque Cliff to your own 1/3 mile Private Beach on the South Shore of Martha's Vineyard.
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