Vacation rentals in Chilmark

4.99 out of 5 average rating, 97 reviews

Renovated Barn in Chilmark 3BR

This renovated barn is a well maintained ranch/cottage style home that is located just off of North Road, minutes from Menemsha. An open living dining/kitchen area make for a welcoming area. It has a breakfast bar, vaulted ceilings, flat screen TV, lovely back deck, outdoor shower, 2 full bathrooms and 3 spacious bedrooms. The house is located just across the street from Menemsha Hills conservation area, providing hiking trails and access to North Shore beach. Lucy Vincent and Squibnocket Beach stickers are also available. Help with boat tickets available.

4.95 out of 5 average rating, 91 reviews

Guesthouse in Menemsha

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

4.91 out of 5 average rating, 127 reviews

Guest suite in Menemsha

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

4.96 out of 5 average rating, 27 reviews

Fun, Authentic, Waterfront Cottage/air conditioned

This authentic beach cottage is centrally-located in the fishing village of Menemsha with stunning views of the sunset, the harbor, the beach and Menemsha Creek. Charter a fishing boat in the harbor across the street or spend the day on the beach just a few steps away. As you meander back to the house, pick up fresh fish to grill on the deck or pre-cooked lobsters and steamers. If you prefer to eat out, rinse off in the outdoor shower and take a walk around the corner to dinner with a view.

5 out of 5 average rating, 56 reviews

Apartment in Menemsha

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!

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.

4.98 out of 5 average rating, 206 reviews

Apartment in Oak Bluffs

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.

4.98 out of 5 average rating, 215 reviews

Guesthouse in Menemsha

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.

Superhost

4.83 out of 5 average rating, 59 reviews

Chilmark Cape in private wooded setting

A recently renovated country home located in the Vineyard's most idyllic town. This 4 bed/2 full bath home offers you an updated kitchen, open living area, spacious bedrooms, outdoor shower, private back deck, and grassy yard on 3 acres of wooded land. And staying in Chilmark allows you access to the best beaches on the island. 2025 Season: I have transferable ferry tickets for July 20th-July 27th only. Please inquire.

5 out of 5 average rating, 76 reviews

Guesthouse in Menemsha

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.

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.

5 out of 5 average rating, 46 reviews

Home in West Tisbury

Idyllic renovated home across from Seth's Pond

Idyllic renovated farmhouse across from Seth's Pond and 0.6 miles from the infamous Lamberts Cove beach. Enjoy the views from the expansive enclosed front porch, play in the 2 acre yard and relax on the back patio with hardlined gas grill. Brand new kitchen, many recent renovations and a fully stocked home ensure a comfortable stay

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Other great vacation rentals in Chilmark

5 out of 5 average rating, 4 reviews

Serene Chilmark Cottage

DianeRating, 5 stars70 months ago

We were looking for a quiet, clean, mildew free place in Chilmark, and we found it! This was a great house for our family of 4. Location is great, close to Alley's and a quick easy drive to Lucy Vincent Beach and Chilmark General Store. We had a small problem with the water heater a few days in and Heather was super responsive and had it fixed the next morning. We had a great stay and would love to stay there again in the future.

Apartment in Aquinnah

4.7 out of 5 average rating, 23 reviews

Quiet & Serene in Aquinnah

StephanieRating, 5 stars9 months ago

Lovely stay here in this pristine part of the Vineyard. Expect shabby chic. Would definitely stay again. The location cannot be beat and the hosts were very kind and accommodating!

5 out of 5 average rating, 9 reviews

Cottage in Fairhaven

“Valhalla” on West Island

RachelRating, 5 stars7 months ago

We had a great time, thanks!

4.75 out of 5 average rating, 4 reviews

Vineyard Family Escape | Beach Pass, Deck, Private

ColemanRating, 5 stars1 month ago

Carolina was a gracious host and we enjoyed our stay at her home. She was a very responsive communicator. We would definitely stay with her again.

4.98 out of 5 average rating, 53 reviews

Historic Brick Barn in Chilmark

ToddRating, 5 stars9 months ago

What a wonderful stay! My family and I thought the brick barn was perfect for us. Private, tranquil, beautiful surrounding countryside, but still easy drives to all Martha’s Vineyard has to offer. The historic building and modern renovation perfectly meshed for maximal modern comforts and impressive historic architecture.

5 out of 5 average rating, 5 reviews

3BR water-view with deck, balcony, & washer/dryer

OlliRating, 5 stars9 months ago

This place is an unusual gem - close walking distance to Lobsterville Beach, which is beautiful and very uncrowded, a quick drive to Chilmark General for any needed supplies, very private and peaceful, outstanding views from the decks and the main bedroom. The house itself has an incredibly charming beach house vibe; it's well worn and hand-made feeling, but scrubbed clean and updated in the places you want it to be - kitchen and bathroom, the decks are new etc., and the furniture is nice and clean. There is a great outdoor shower, and plenty of beach gear (umbrellas, chairs, boogie boards, lots of books, etc). This is the quiet end of MV, and this house is not full of high end furnishings and fancy amenities. But if you are looking for an incredible location and a beautifully private, calm, authentic feeling place full of charm, you can't do much better.

4.97 out of 5 average rating, 33 reviews

Cottage in Menemsha

Vintage Chilmark Retreat

HowardRating, 5 stars10 months ago

William is the consummate host of a wonderful cottage! He is very helpful and quickly responds to any questions that we had. He is a charming man with a good sense of humor and positive demeanor. I always enjoy communicating with him. The cottage in Chilmark is cozy and private, located on one of those Martha's Vineyard dirt roads in the woods not far from the best beach on the island, Lucy Vincent Beach! We have just returned from our fifth visit and can hardly wait to return next year!