Vacation Rentals By Owner In Chilmark, MA

Japanese inspired, Mid-Century Modern beach house with sweeping views of Menemsha pond, Vineyard sound, Aquinnah. Pond access via path. Stunningly bright, airy & renovated in '20 with open floorplan, large decks, outdoor shower, central air, 4 car parking. Walk to Menemsha harbor, public beach, fish markets, Galley restaurant. Large yard with lily pond, grape vines, blueberry bushes. Gas grill, variety of outdoor seating, couch, lounge chairs & dining table. Beach sticker option to renowned Lucy Vincent or Squibnocket. Ideal for relaxation, unwind, unplugging, quality times with loved ones. At night you can marvel at a bright starlit sky or abundant summer fireflies. Dream location for a read-away. Feel like a local buying fresh eggs from nearby farmstands, or fresh fish unloading daily at Menemsha docks. Relaxing and revel in stunning nature. Enjoy central air, laundry, Gigabit Wifi. We love dogs, they love the large grass yard. Take in Vineyards best beachs, stunning nature, relaxed & simple getaway. .4 miles (7 mins walk) on dirt rd to Menemsha Pond where guests can launch paddle board, canoe, or kayak (BYOB).brbrNOTE: Our smaller 2bed 1bath Guest house (ideal for 1-3 adult guests ) located across a stream & small bridge may be available to rent together if the dates align. VRBO 2604183 to search it.brbrBike storage avail in Shed.brbrNote: our repeat renter reserved June 15 -October. Our smaller guest house next door may be open. Check out VRBO id 2604183

Menemsha Pond views & access! Mid-century renovated beach house. Dogs welcome.

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

$417.79

Charming rustic cottage located a short distance off South Rd just past Abels Hill in Chilmark. Chilmark is very rual with rolling hills and stone walls. Water views from upper deck. Access to Lucy Vincent beach a mile down South Road and Squibnocket beach by purchasing stickers at town hall.The sound of sheep during the day and the ocean waves at night is very soothing. Views of the night sky can be wonderful since there is no light pollution. A short walk up our road there are scenic and wooded Landbank trails.

Charming Rustic Cottage

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

$503.08

*** 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

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

Chilmark, Massachusetts, United States

3

Bed

Bath

Sleeps

$3329.39

Our family home is a 4-acre waterfront paradise with wonderful sunsets. The private location sits between a large wooded hill and a 200-acre private estate. The six-bedroom, 4½-bath, two-kitchen main house enjoys dramatic views of the Elizabeth Islands, Tarpaulins Cove, and vistas from Gay Head Lighthouse to Woods Hole. The property has a beautiful lawn that culminates at a spectacular bluff overlooking a private cove and sandy beach—perfect for lawn games, sunsets, and clambakes.brbrHot outdoor showers to rinse off sandy toes! Gas grill ready to use. Sunny deck off the main house.brbrSee the beautiful property: https://www.youtube.com/watch v=12RcoAxq-ssbrbrComfortably sleeps 12; extra loft space and pull-outs accommodate occasional guests. brbrLucy Vincent Beach, Great Rock Bight, Menemsha, Chilmark Community Center, Chilmark Library, and Chilmark General Store are all within a 10-minute drive.

Stunning private family home - spectacular sunsets

Chilmark, Massachusetts, United States

6

Bed

Bath

12

Sleeps

$594.47

Classic Vineyard summer cottage with private waterfront access to cove on Menemsha Pond on 1.5+/- acres within a few minutes’ walk to town dock and beach. br• One level, 3 bedrooms, 2 lavs (one with tub/shower), open living/dining and kitchen areabr• Large front and side decksbr• Private outside showerbr• Washer/dryerbr• Fully furnished (but bring your own bed-sheets and towels)br• Wireless internet accessbr• Outside gas grillbr• Smoke-free, no petsbr• No TV

Classic Vineyard Summer Cottage; Private Waterfront Access; Menemsha Pond Views.

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

$1183.32

Round-trip Transferable Ferry Tickets Available for July 4-11 and July 11-18!brbrPerfect for a family or group of friends who are looking for less than a 2-minute walk to the beach and kayak from the backyard dock. This 4-bedroom, 2 1/2 bath home, sleeps 8. brbrOur home 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 (less than a 2-minute walk)br• Our association's private beach at Zack's Cliff (6 minutes by car, key to gated beach is 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. brbrWalk 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 with an ensuite bath, a queen bed, and direct access to the deck. The other three bedrooms are on the opposite side of the open living area and all have ocean views (one queen and two with two twin beds). A full bath and a 1/2 bath are easily accessible from these three rooms. brbrWhile 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

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

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

$745.52

Everyday is a beach day! A magical beach retreat cottage at the water's edge, nicknamed Gadget. Wades Cove at Chilmark Pond. has immediate, private access to the barrier beach on the Atlantic. just a short canoe paddle away. Swim after breakfast and before dinner, or all day!.Three bedrooms and a large new outdoor shower with beach and water views. Lovingly reimagined. Access to the barrier beach, canoes provided, plus a small aluminum pond boat with oars.Composting toilet and battery powered lighting. This is an off grid experience. All appliances are propane. This perfect cottage has amazing water views and water access on a private family estate.Away from all hustle and bustle. yet only a few minutes to town.Cell service for internet access. Unwind! Find your inner peace and quiet. Get a tan. Read a book. Fall in love.

Chilmark pond side cottage with beach access, sweeping views

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

$1723.37

Best view of sunset on island.brFully equipped modern house; air conditioning, large deck, barbecue, outdoor shower, linens, towels, beach chairs, kitchen with dishes, flat ware, cooking utensils, pots, pans, microwave, gas stove, etc., high speed internet, cable television. Master bedroom with queen bed, second bedroom with two twin beds, sleeping loft with two twin beds, den with queen pull-out sofa bed. Very short walk down path from house to private beach (end of Menemsha Beach) and walk down beach into Menemsha Harbor in 5 minutes.

House in Chilmark/Menemsha, Martha's Vineyard w/ Private Beach, Sunset View.

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

$1097.93

*** brWe have transferrable car ferry reservations ⛴ for guests who would like to book for summer 2026 . Just reach out to us. ***brbrThis charming, rustic cottage is located on Martha's Vineyard iconic north shore with views of Vineyard Sound and the Elizabeth Islands. Located in quiet, pastoral Chilmark, the 40-foot deck has spectacular sunset water views. Follow the path from the backyard down to 3/4 of a mile of private association beach on Vineyard Sound. Enjoy miles of walking trails and access to two association tennis courts. With 4 bedrooms, 2 bathrooms, and an outdoor shower, it comfortably sleeps 8. Air conditioning, high speed internet, and access to Chilmark's famous private beaches (Lucy Vincent, Squibnocket, and Menemsha Pond) make this home an ideal destination for your next vacation! brbrPlease note that there is a 7-night minimum stay and Friday is the turnover day.brbrWhat to ExpectbrbrWhen you arrive at Chilmark Cottage, the first thing you will notice is the view. Virtually every room in the house has a water view. Multiple sets of sliding glass doors provide exquisite views of the water and easy access to the deck, which spans the entire back of the house. The deck has a grill and a dining area that comfortably seats 8.brbrThe main floor has two bedrooms. The front bedroom has a king-size bed. Across the hall is a full bath with a shower/tub combination. The back bedroom has a full-size bed, a desk, and views of the water. The kitchen, dining area, and living room complete the main floor and all have water views. The outdoor shower is located on the side of the house. A quaint circular staircase leads you upstairs where you will find two more bedrooms and a full bathroom with a shower stall. Each of the upstairs bedrooms has two twin beds (4 beds total) and views of the water. brbrOnce you settle in, you’ll want to explore. Follow the backyard path down to a trail that leads to the private association beach. It’s about a five-minute walk. Or, if you prefer a bit more exercise, there are 3 miles of private walking trails around the association which can lead you over to Great Rock Bight Preserve’s public trails. There are also two private association tennis courts you can enjoy during your stay.brbrWhat Makes This Place Special brbrAs one of the original homes in Spring Point, this remarkable piece of the Vineyard was lovingly passed down through the same family for over 50 years. They decided to sell it in 2022 and we knew right away that it was a rare gem. Sitting on over 3 acres of wooded north shore land, the home has stunning views of Vineyard Sound and the Elizabeth Islands. The sunsets from the back deck are nothing short of magical. There are over 68 acres of common land in Spring Point, 3 miles of walking trails, and 3/4 of a mile of private beach. We fell in love with this place the moment we saw it. Since acquiring it, we have taken great care to balance bringing in modern amenities while maintaining the home's rustic Chilmark charm. We hope you will love it as much as we do!brbrUnique Benefitsbrbr- Spectacular water views from virtually every room in the house.br- 5-minute walk to the beach (just follow the path from the backyard!).br- 3/4 of a mile of private association beach.br- Access to 2 private association tennis courts.br- 3 miles of private walking trails that also connect to Great Rock Bight Preserve.br- 40-foot-wide deck - perfect for dining, entertaining, or taking in the magical sunsets.br- Private, wooded lot on over 3 acres.br- Nestled in an association with over 68 acres of common land.br- Access to Chilmark's famous town beaches, including Lucy Vincent and Squibnocket.br- Zero light pollution, with millions of stars visible with the naked eye

Spectacular Chilmark Sunset Water Views, Walk to Private Beach, Trails, Tennis!

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

$710.09

The Little House was built in 1960 as a one room studio/cabin. Since then a gourmet kitchen wing has been added, as well as a detached bunkhouse. The main structure has an open floor plan with bright living and dining room area with skylight and a woodstove, and a full kitchen with center island. Through a covered causeway is a large master bedroom with a queen bed, and just off the back, past the outside shower, a detached bunkhouse with a twin bunk bed, and double bed. The property is perfect for two couples or a family with kids.brbrWhile having an authentically vineyard feel, the Little House has been updated to meet the needs of our time, with a heat pump system (including in the bunk house) for cool or sultry nights, dishwasher, wifi and television. brbrThe large deck is great for lounging but there is also a deeded right of way to Menemsha Beach (ten minute walk) . Lucy Vincent and Squibnocket beaches are ten minute drive away. (Beach stickers are available at the Chilmark Town Hall.)br

Bright and cozy menemsha cottage

Chilmark, Massachusetts, United States

2

Bed

Bath

5

Sleeps

$1096.08

Located just a 5 minute walk from Chilmark's famous North Tabor Farm, this charming house is a dream for families or groups. brbrThe house has 5 bedrooms, 4 with a queen bed plus one bedroom with both a twin bunk bed and a queen. There are 3 full bathrooms plus an outdoor shower which is perfect after a long day at the beach! Linens, toiletries and basic kitchenware/ingredients included. brbrThe house has 2 decks. One has a fire pit, couches, grill and outdoor dining set up for 10. brbrThe house comes equipped with beach chairs and toys, kayaks, board games and half basketball court. brbrThere is a den and family room with ample seating and 65 tv. Up to date kitchen appliances and fixtues. brbrWe hope you enjoy what our home and Chilmark has to offer!

5-bedroom, 3-bath house on 5 Acres in Chilmark

Chilmark, Massachusetts, United States

5

Bed

3

Bath

10

Sleeps

$4073.7

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. Enjoy family gatherings in the large, open kitchen connecting to a spacious living room with wet bar. Large sliders providing access to the deck from the living room and kitchen. Named appropriately, it is an ideal location for clamming, kayaking and sailing. Town access to Squibnocket Beach and Lucy Vincent Beach. Dock shared - oyster float on right side of dock and checked every couple of days. Broker owned property.brbrBR1 King en suite with shower, 1st floorbrBR2 California King, En suite with tub/shower combo, 2nd floorbrBR3 Queen, lower levelbrBR4 Twin trundle, lower levelbrHall bath tub/shower, lower levelbrPowder room and Two outside showers

CHILMARK WATERFRONT WITH PRIVATE DOCK

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

$596.33

Wonderful screen porch overlooking gorgeous setting. Right off South Road, a few minutes to fishing village of Menemsha and Lucy Vincent beach. Short walk to Landbank at Chilmark pond and paddle across to ocean beach.4 bedrooms, 2 baths. One floor. New 2 zone heat/air conditioning system. New outdoor shower. Newly painted. New deck. New windows. Propane grill. Nespresso + capsules provided. Kayaks. Pet friendly. Great for either a couple or up to 8 people.

Beautiful Chilmark beach house. Great screen porch. Fun house. Pet friendly.

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

$1103.0

Summary:brbrHillside OakbrbrbrbrThe Space:brbrNestled in the serene scrub oak forest of Chilmark, this stunning 4-bedroom home offers a perfect retreat for families and friends seeking a peaceful getaway on Martha's Vineyard. With an open floor plan and an abundance of windows, the contemporary design allows natural light to flood the space, creating a warm and inviting atmosphere. The home features two queen beds and two double beds, accommodating up to eight guests comfortably. Enjoy the convenience of a fully equipped kitchen, complete with a new stove and modern appliances, perfect for preparing meals together. Step outside onto the expansive patio and take in the tranquil surroundings, or fire up the gas grill for a delightful barbecue under the stars. The property is dog-friendly, so you can bring your furry friends along to enjoy the lush outdoor space. A short 10-minute walk leads you to the private Brickyard beach, where you can relax and soak up the sun, while the nearby Menemsha Hills and Brickyard trail system offer miles of scenic hiking paths for outdoor enthusiasts. Located just a short drive from some of the island's most beautiful beaches, including Lucy Vincent Beach and the vibrant town of Oak Bluffs, this home is ideally situated for exploring all that Martha's Vineyard has to offer. With the Vineyard Haven ferry only 15 miles away, you can easily venture off the island for day trips or excursions. Whether you're looking to unwind in nature, enjoy family game nights with the provided board games, or explore the local attractions, this Chilmark home is the perfect base for your island adventure. Book your stay today and experience the beauty and charm of Martha's Vineyard!

Private Hillside Home, Fully Equipped Kitchen, Dog-Friendly, A/C, W/D

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

$1108.14

Summary:brbrThe Eliot NoyesbrbrbrbrThe Space:brbrEnjoy the beauty of Martha's Vineyard in classic mid-century style at this four-bedroom Chilmark home! This is a unique and secluded architectural gem with a private swimming pool and deck, beautiful ocean views, and nearby access to some of the island's most sought after beaches. Built in 1964 by the award-winning architect Eliot Noyes, of The Harvard Five, the residence was featured in Life Magazine. This iconic single-level home sits just five minutes from Menemsha beach. The property is wonderfully private, yet it's also only three minutes from Lucy Vincent Beach and three miles from the recently renovated Squibnocket Beach; both of which can be accessed by bringing the rental agreement to town hall at Beetlebung Corner for the permit. With exterior walls constructed almost entirely of floor-to-ceiling glass, this oceanview home is composed of three components closely connected by covered decks. It’s the perfect place for a family getaway, a stylish retreat, or a beach vacation with close friends. Step inside the open living space to find an abundance of mid-century design, exposed wood ceilings, and plenty of seating for your guests. Admire the views of the ocean and the surrounding trees and garden as you choose a book from the shelves, sit down to play a board game, browse the WiFi, or curl up by the flatscreen cable TV. Wake up each morning with the help of the Nespresso machine in the kitchen, which also features open shelving and a dishwasher for your convenience. Flip pancakes and scrambled eggs with your kids and sit down as a family around the dining table for eight. You'll be only a short drive from Menemsha, Lucy Vincent, and Squibnocket Beaches, but you'll also have access to a gorgeous private swimming pool. Sunbathe on the deck with a cocktail in hand, play a game of cards at one of the patio tables, and then light the gas grill for an afternoon barbecue. The yard, enclosed by a beautiful stone wall, offers a wonderful space for picnicking, playing and relaxing, while the outdoor shower and private washer/dryer help keep the sand and grass outside. With four bedrooms (that are separate from the main living area) and two bathrooms, The Eliot Noyes will accommodate as many as eight guests. You'll find one king bedroom, one queen bedroom, and two bedrooms with a set of twin beds apiece - each of which opens onto a gorgeous, private deck space. Known for its tranquil atmosphere and scenic natural beauty, Chilmark is the perfect place to escape the hustle and bustle of everyday life. Spend your days basking in the sun on Menemsha Beach or pick up a pass to access the private stretches of sand at Lucy Vincent and Squibnocket Beaches. You'll also be just three miles from the Menemsha Hills Reservation, a 211-acre expanse that is ideal for hiking among wetlands, woodlands, and the island's second-highest peak. Come and experience this stunning glimpse of island life. Book your getaway at the Eliot Noyes House on Martha’s Vineyard today!

Iconic Mid-Century Home with Gorgeous Ocean Views, Private Pool & Decks

Chilmark, Massachusetts, United States

2

Bath

Sleeps

$545.53

Summary:brbrChilmark Guest HousebrbrbrbrThe Space:brbrTucked away in a private glen on three secluded acres, this light-filled home in Chilmark is Martha's Vineyard at its most peaceful. It's the perfect escape for beach-goers, as it sits within minutes of Menemsha (three miles), Lucy Vincent Beach (four miles), and Squibnocket Beach (five miles). The house enjoys a beautiful, natural setting, with thickets of woods surrounding the grassy lawn. On summer mornings, ride your bikes or walk less than two miles to the tranquil expanse of Great Rock Bight Preserve. Upon your return, linger outside on the deck and sip a steaming cup of coffee in a rocking chair. It's a joy to come home after a day at the beach, as you light the gas grill, set the outdoor table for a sunset dinner, and watch the kids release any lingering energy on the outdoor play structure. Back inside, lofty ceilings, exposed cross beams, and large panes of glass bring in an abundance of light and nature. As a result, you'll feel surrounded by the island's beauty as you cook in the kitchen, play board games at the table, and stream movies in the living room. Both bedrooms open to the deck, one of which is a charming children's room with bunks and a selection of toys and books. A private washer/dryer and complimentary WiFi are provided for your comfort and convenience as well. bThings to Know/b

Peaceful, dog-friendly home on 3 acres with lovely yard, near beaches

Chilmark, Massachusetts, United States

2

Bed

Bath

Sleeps

$2055.28

Gracefully situated atop the hills of Spring Point in Chilmark, our 4br BR (sleeps 8-10) home features panoramic water views sweeping from the Gay Head light house to the Elizabeth Islands. brbrThis 4,750 sq-ft family sanctuary was designed to balance inside and outside family gathering spots with private spaces for couples or kids, cooks or book lovers, sports enthusiasts or WFH professionals. Experience everything Chilmark and Martha's Vineyard has to offer. brbrMinimum stay requirements:brMay 16 through June 26 - four (4) night minimum stay.brJune 27 through September 15 - seven (7) night minimum stay. brSeptember 16 through May 15 - four (4) night minimum staybrbrProperty details: The primary suite includes a king bed, fireplace, luxury bathroom, laundry, loft with twin beds and private patio. The adjacent office offers privacy and is equipped with printer, wifi, and landline telephone. brbrAt the opposite end of the house, a generous guest room has a king bed and en-suite bath with direct access to a large deck.brbrThe great room is anchored by a floor-to-ceiling fireplace with wall-to-wall windows facing the water and direct access to the deck and yard. This room includes a wet bar, TV, game closet and extensive CD and DVD library. brbrThe well-equipped kitchen and bright dining area has seating for 12, direct access to the deck, and adjacent powder room. Directly off the kitchen is the garden courtyard to enjoy coffee in the morning sun and includes a propane grill for evening dinners.brbrThe ground floor has two suites joined by a galley kitchen. The first suite includes two bedrooms (twins and double) with shared bath, laundry room with utility sink, sitting room with TV and pull-out queen bed. The second suite boasts a large family room with TV, extensive library, fireplace, queen sleep sofa, and en-suite child-friendly bath. Each suite has its own staircase to the main living area, and direct access to patio, yard, and upper deck. brbrAdditional features: Central AC, enclosed outdoor shower, large book and music library, high-speed internet, printer, 3 TVs, firewood, beach chairs, towels and toys. Association amenities include tennis courts, private beach, and extensive trails.

Amazing sunsets, a welcoming home, and island adventures. Lifetime memories!

Chilmark, Massachusetts, United States

5

Bed

Bath

10

Sleeps

$502.65

Unwind Up Island at this summer cottage, nestled in the woods and a short walk to Chilmark Pond. A canoe or kayak are just 5 minutes down the walking path to take you on a paddle ride to a private beach. brbrOne side of the wraparound porch has a fixed roof and the other side has a retractable awning - lovely options to enjoy some serenity, a beverage, a full meal or just the natural beauty of the island. Inside, two charming bedrooms, and open kitchen/dining area/living space provide casual comfort. Upstairs is a loft with a double futon and there's even a private outdoor shower. Easy living here if you want quiet and cozy!brbrTen minute drives to either the Chilmark General Store or Alley's General Store for local vibes. Twenty minutes to Vineyard Haven, Oak Bluffs or Edgartown for shopping and night life. Or enjoy a quiet sunset at the Menemsha Harbor.brbrMinimum stay one week; check in is 10 am; check out is 3 pm.brbrAlso - we know it's a challenge to get on/off island. Be sure to check Ferry Schedules and suggest dates if the Saturday-Saturday is not available. You can also waitlist, which usually works, but isn't a guarantee. You can also look into renting a car on island - seems a bit pricey at first, but when you tally the roundtrip boat ticket, it can be a bit more manageable.brbrBest wishes on finding some island time!

Quiet 2-bedroom cottage in Chilmark, MA Martha's Vineyard

Chilmark, Massachusetts, United States

Bed

Bath

Sleeps

Select Dates for Price

Simpler, secluded living, just 5 minutes walk through woods to a gorgeous private beach, where stairs lead down from a spectacular cliff-top view of the Island's entire south shore. This lovely rental offers relaxation in a comfortable, informal, well-equipped converted 19th-century carriage barn. You'll be nestled in one of the largest and most secluded estates on the Island, Windy Gates in Chilmark (the quiet end of Martha's Vineyard). There you can revel in the waves of one of the world’s most beautiful beaches, or take a short, forested walk to a meandering trout brook. brThe Windy Gates barn's 40' X 26' open plan downstairs features ten-foot ceilings, and rich lacquered wooden walls with huge vintage photographs of Island scenery. Sliding barn-doors and French doors open to let in summer light and air. In addition to the cozy conversation area, there’s a small media corner and an office space with wireless internet and unlimited national calling. The eat-in kitchen seats ten. The full bath downstairs is supplemented by an outdoor shower, washer and dryer. brUpstairs is four bedrooms and a half bath; the sunlit master bedroom runs the width of the house. Woods shade the house on two sides; the others are open and sunny. Outdoor accommodations include a grill, picnic table, fresh-air clothes line and comfortable lawn furniture. This is a healthy, eco-friendly retreat. We use only proven, greener cleaners, and non-toxic products. It's smoker and pet-free, with no rugs or curtains (washable shades only), and all mattresses and pillows are fitted with hypo-allergenic covers. Thinkers, artists, craftsmen and just plain private people have cherished this unusual, quiet retreat for generations, returning time and again. Find out why for yourself.brbrWEEKDAY TO WEEKDAY BOOKINGS ONLY PLEASE! Discount available for stays of two or more weeks.

Peaceful Scenic Up-Island Retreat With Private Martha's Vineyard Beach

Chilmark, Massachusetts, United States

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Bath