Vacation rentals in Chilmark Pond

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Top-rated vacation rentals in Chilmark Pond

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Guest favorite

The exterior of the barn features wooden double doors that provide access to the interior. A stone wall runs along the garden, accompanied by seating areas consisting of a picnic table and two chairs. Lush greenery surrounds the property, enhancing the secluded feel.

Guesthouse in Chilmark

4.95 out of 5 average rating, 91 reviews

Beautifully Renovated 1800s Chilmark Barn

Beautiful 2-story private barn in Chilmark on Martha's Vineyard. Secluded yet convenient. Perfect for a couple or a couple with older children (space not good for those with mobility issues). Downstairs living area, dining area, fridge, toaster, coffee maker, half bath -- shower is outside in the private garden. Loft-style sleeping area upstairs (2 private sections). 2 friendly labs and 5 chickens on premises. Walk to Chilmark Store, easy bus access. Walk-on pass to town beaches, no car pass

Guest favorite

The exterior of a modern barn house is visible, featuring a black shingle facade and multiple skylights along the sloped roof. A private entrance is framed by a small, leafy tree, with a stone pathway leading through a lush green lawn.

Guest suite in West Tisbury

4.91 out of 5 average rating, 127 reviews

Studio Guest Suite in Modern Barn House

A beautiful guest suite on Martha’s Vineyard with a private entrance on the back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this airy suite has vaulted wood ceilings with skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is prime and centrally located, just off historic Music St, a short walk to our small town center which provides many amenities. Ask about our other private guest suite if you are traveling with others

Guest favorite

A stone patio is visible in front of double French doors, which are framed by a modern, dark trim. Two wicker chairs and a matching table are placed on the patio, with a small potted plant as the centerpiece. Natural light reflects off the doors, adding to the serene setting.

Apartment in West Tisbury

5 out of 5 average rating, 56 reviews

Butterfly Farm Sanctuary Bright Sunny Studio Apt

Spacious & serene in a rural natural setting of West Tisbury. Private, modern, light-filled studio on the first floor walkout of a newly built 2021 post and beam home. Beautifully landscaped, abutting the state forest. Full amenities, 10ft high ceilings, windows and French doors with stone patio sitting area. Studio is down a long dirt driveway located mid-Island, near beaches, trails, and all towns. Just a mile to the Farmers Market, Artisan fair & Alley's General Store. The perfect retreat!

Guest favorite

A set of wooden steps leads to a bright red door, framed by wooden beams and natural greenery. The outdoor area features a lawn that blends with the surrounding landscape, creating a welcoming entrance to the studio.

Guesthouse in West Tisbury

4.96 out of 5 average rating, 74 reviews

Vineyard Meadow Artist Studio

This lovely artist's studio is just steps from miles of trails. Walk to the beach or meander through the woods of Long Point Wildlife Refuge, experiencing the serenity of this still untouched corner of Martha's Vineyard. This studio includes a bathroom with a shower, a washer/dryer and a kitchenette. It is the perfect spot for a lone artist, a couple or a family to enjoy Martha's Vineyard any time of year. This property shares the driveway and parking with Vineyard Meadows Writer's Cottage.

Top guest favorite

A wooden deck is visible, showcasing a simple bench and a couple of potted plants. Lush green grass and a variety of trees and flowering bushes create a serene garden setting, inviting quiet moments outdoors. Light filters through the greenery, enhancing the peaceful atmosphere.

Apartment in Oak Bluffs

4.98 out of 5 average rating, 206 reviews

Sunny Studio Apartment on Martha's Vineyard

Our Sunny Studio is centrally located on Martha's Vineyard. A down-island location with an up-island feel. Open and airy studio with kitchenette and bath. The apartment has all the essentials. The apartment is located within walking distance of hiking and biking trails. A 10 to 15 minute car ride to any down-island town / beach. ***Please Note: Although conveniently located we are not within walking distance to Bars or Restaurants. We do recommend first time visitors rent or bring a car.

Top guest favorite

A spacious bedroom featuring a wooden bed frame and a large bed with neutral bedding. A colorful wall art piece adds visual interest above the bed. Natural light enters through two windows, and a full-length mirror is positioned nearby on one side.

Apartment in Falmouth

4.97 out of 5 average rating, 225 reviews

Modern Luxury Apt. | 7 min from Commons

This luxury 1Br + 1bth apartment is the perfect getaway. - 650 square feet, newly renovated - 15 Minutes from Old Silver Beach, South Cape Beach, and Falmouth Heights beaches - Steps from 1,700 acres of walking trails (Crane Wildlife) - 7 minutes to Mashpee Commons (shops and restaurants) - 15 minutes to Main Street Falmouth - 13 minutes to Ferry for Marthas Vineyard - 85” smart TV - 5 minutes to Shining Sea Bike Trail - Coffee/Espresso Machine - 2 minutes from Paul Harney Golf Course

Guest favorite

A porch area is depicted with several black rocking chairs arranged on wooden flooring. A cream-colored tote bag with 'CHILMARK' printed prominently sits on the floor beside the chairs, suggesting a relaxed atmosphere for outdoor enjoyment.

Guesthouse in Chilmark

4.98 out of 5 average rating, 215 reviews

Beautiful Guest House in Chilmark

This newly renovated guest house is located in a quiet and very private setting in Chilmark. The guest house is located above the garage adjacent to the main house with a private entrance. It has a queen size bed with two oversized chairs. There is a full bathroom in addition to a private outdoor shower. A small kitchen features butcher block countertops, a stainless steel sink, refrigerator and electric stove. Central air conditioning + heat make it the perfect getaway for all seasons.

Top guest favorite

A wooden deck is shown with outdoor seating, including a table and chairs. Surrounding the deck are blooming rose bushes and lavender plants, adding vibrant colours to the natural landscape. The space is bordered by natural stone and pebbles, leading into a wooded area.

Cottage in Tisbury

4.98 out of 5 average rating, 342 reviews

Martha's Vineyard Getaway Cottage

Contemporary cottage on quiet, private, wooded lot. Pristine, bright & comfortably furnished. Open living area, hardwood floors, vaulted ceilings, indoor/outdoor fireplaces, well appointed kitchen, washer/dryer, cable/internet/phone with unlimited national calling, SmartTV with Netflix and additional internet streaming services. Walk or bike to beaches and trails, 5 minute drive from downtown shops and restaurants. Property abuts West Chop Woods with lovely, quiet walking trails.

Top guest favorite

A modern kitchen area is showcased with stainless steel appliances, including a refrigerator and a dining table. The adjacent living space features a light-colored sofa paired with a side table, bringing together comfort and functionality. A door leads to the outside, enhancing accessibility.

Guest suite in Falmouth

4.99 out of 5 average rating, 153 reviews

Pet-Friendly Apt close to West Falmouth Beaches!

Kick back and relax in this calm, stylish space! This comfortable and peaceful guest apartment is situated in an ideal location in a quiet, beautiful neighborhood that is close to beaches and a short drive to downtown. Take a quick stroll to the West Falmouth Market or the Shining Sea Bike Path. With easy access to Chapoquoit & Old Silver Beach, this perfectly situated apartment is in an ideal spot for your next Falmouth getaway!

Top guest favorite

A screened-in porch features a wicker couch adorned with soft pillows, providing a comfortable seating area. Natural light pours in through multiple windows, allowing views of the lush greenery outside. A wooden table and a single chair offer additional seating options.

Guesthouse in West Tisbury

5 out of 5 average rating, 76 reviews

Country cottage walk to Alley's General Store

This sunlit summery cottage is in a very quiet, private and pastoral setting, situated 100 feet from the small Tiasquam River, with many birds chirping in the abundant vegetation and trees nearby. Because of the river's proximity, the cottage has a Composting Toilet. My wife and I live on the property uphill from the cottage. The property is in the countryside but a 5 minute walk to the local town center.

Top guest favorite

A well-lit staircase is visible, featuring beige carpeting with a subtle striped pattern. A wooden handrail runs along one side, leading upwards. At the top of the stairs, a framed picture is mounted on the wall, adding a touch of decoration to the space.

Guest suite in Oak Bluffs

4.99 out of 5 average rating, 168 reviews

Quiet Hide Away

Lovely efficiency suite with private entrance in a quiet neighborhood. Private space located over attached garage. Plenty of space for two guests. Comfortably appointed with queen bed, dining set, living area with tv and full bath. Enjoy a coffee or cocktail on the private deck. Toaster oven, refrigerator and coffee maker will start your day right before heading to nearby beaches, golf courses or shopping.

Guest favorite

The exterior view of the guest cottage features a charming wooden facade with a welcoming front door. A landscaped yard showcases green grass, flower beds, and a stone pathway leading to the entrance. Adirondack chairs are positioned nearby, providing a comfortable spot for outdoor relaxation.

Cottage in Tisbury

4.9 out of 5 average rating, 167 reviews

Sweet Cottage w/ yard, 1.5BR, Walk to Town & Water

Lovely 500 sq. ft. guest cottage on peaceful, residential hilltop near town & water. Open kitchen & living area; bedroom with double bed; sweet office accessed only thru BR with twin-sized couch; queen sofabed in LR. Walkable to parks, beach and town for kids and adults! Fenced in yard w bbq, outdoor shower and a brand new fire pit. A true pleasure. Read more below!

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Popular amenities for Chilmark Pond vacation rentals

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Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Chilmark Pond

A tranquil beach scene is depicted, showcasing soft sands leading to calm waters reflecting hues of orange and pink from the sunset. The horizon is gently illuminated, creating a serene atmosphere. The smooth shoreline curves alongside the peaceful water, providing a sense of openness.

Home in West Tisbury

5 out of 5 average rating, 4 reviews

Large home in West Tisbury w/private beach access

EricRating, 5 stars9 months ago

We spent a week at this gem of a house with our friends and their kids (a total of 8 of us) This is my kind of beach house: big enough but still cozy, lots of fun decorations and tasteful art and furniture, ample places to sit, eat, play, and relax both in- and outdoors, enough bathrooms, multiple sleeping “zones” so our two families could co-exist nicely, and it has a lived-in welcoming feeling throughout. The kitchen may be a tad small but it actually has the things you need to cook, plus a beautiful dining area with a solid oak table. And the location is incredible: it feels secluded, yet is a ~5 min walk to 7a and the rest of west tisbury, and a 5 min drive to grey barn for morning pastries. We enjoyed gazing up at the stars and Milky Way most nights after the kids went to sleep. Access to Quansoo is the icing on the cake, if you haven’t been and you like the beach you are in for a treat..

Guest favorite

A cozy window seat features a soft, fluffy cushion adorned with multiple decorative pillows. Large windows frame an outdoor view of leafless trees, allowing natural light to illuminate the space. A wooden deck is visible outside, complementing the inviting nook.

Home in Chilmark

5 out of 5 average rating, 11 reviews

Beautiful Middle Road, Chilmark

LaurenRating, 5 stars11 months ago

Very nice place! Larger than pictures and super relaxing! Beautiful upstairs primary bedroom shower- large & seems to be very new. Loved this place. Chilmark is a great area + host was very responsive! Would absolutely love to stay here again. Thank you prudy 10+/10!!!

Top guest favorite

A cozy living area features a light-colored sofa adorned with cushions next to a wooden table. Sunlight filters through window shades, illuminating the space. A vintage wooden box holds a bouquet of flowers, while wicker chairs provide additional seating, creating a relaxed atmosphere.

Home in Chilmark

5 out of 5 average rating, 16 reviews

The Blueberry House on Martha’s Vineyard

ColleenRating, 5 stars9 months ago

We enjoyed our stay at The Blueberry House. Very private and peaceful. Beautiful country roads and scenic areas. We recommend if you are looking to get away from the hustle and bustle

Guest favorite

Home in Chilmark

4.86 out of 5 average rating, 49 reviews

Cozy Waterfront Cottage, Newly Remodeled!

MarlaRating, 5 stars9 months ago

Another wonderful stay at this magical spot!

Top guest favorite

A modern kitchen showcases stone countertops and gray cabinetry, with a large window offering views of the surrounding landscape. Stainless steel appliances, including a dishwasher, complement the space. Natural light floods the room, emphasizing the welcoming atmosphere of the open layout.

Cottage in Fairhaven

5 out of 5 average rating, 9 reviews

“Valhalla” on West Island

RachelRating, 5 stars8 months ago

We had a great time, thanks!

A wooden deck features a round dining table surrounded by chairs, providing a dining space. Two vibrant red chairs are positioned nearby, creating an inviting area for relaxation. A striped umbrella adds shade, while lush greenery is visible in the background.

Home in Aquinnah

4.7 out of 5 average rating, 10 reviews

Secluded Aquinnah Cottage

ElanaRating, 5 stars9 months ago

What an incredible find! This cottage is a little slice of heaven. Located down a private dirt road that we didn’t have any issues navigating. The road is common of the back roads on MV. Not an issue for most cars, but you wouldn’t want to drive a low riding sports car down. The property is hard to beat, especially at night. You have an amazing view of the stars and sky. I sat on the deck every night star gazing and listening to the waves crash against the cliffs. I should also mention the property was shockingly not too buggy. We could sit outside with a citronella candle and manage not to get eaten alive by mosquitoes. Same goes for inside. We didn’t find any creepy crawlies inside either which was refreshing. Cottage itself is clean and well equipped. The grill and fire pit are also in great condition. The bedroom has great big windows over looking the woods and a comfortable bed. It was the perfect breath of fresh air we needed.

Top guest favorite