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, 28 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.

5 out of 5 average rating, 47 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

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Chilmark vacation rentals

Self check-in

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Other great vacation rentals in Chilmark

Cottage in Chappaquiddick

4.97 out of 5 average rating, 66 reviews

Chappy cottage close to ferry & walk to beach

AnthonyRating, 5 stars2 weeks ago

We have been to MV many times, but never stayed on Chappaquiddick. Peter’s cottage was peaceful and relaxing. Isolated from the crowds of downtown Edgartown, but also so easy to access all the benefits of Edgartown restaurants and shopping by the Chappy ferry. Never had to wait for a ride over to the main island. The cottage had everything we needed and was just what we were looking for. Peter was a gracious and responsive host.

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.

Cottage in Menemsha

4.88 out of 5 average rating, 8 reviews

Chilmark, Martha' s Vineyard Water View Cottage

ArthurRating, 5 stars9 months ago

We had an excellent week at Robert’s cottage. Just what we needed to get away for a while. The cottage was extremely comfortable and well equipped. The surrounding property was beautiful and very peaceful. We would definitely return again to stay!

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 stars8 months ago

We had a great time, thanks!

4.96 out of 5 average rating, 25 reviews

Home in West Tisbury

Charming Lambert's Cove home on Martha's Vineyard

KatelynRating, 5 stars8 months ago

I could not recommend staying at Brad and Elliott’s enough. They were incredibly kind, accommodating, and communicative. Their house is positively gorgeous and in such a beautiful, peaceful area. They thought of absolutely everything for our stay, including suggestions and tips for where to go and how to get around. We hope to be visiting and staying at Brad and Elliott’s again soon!

Home in West Tisbury

5 out of 5 average rating, 4 reviews

5 minutes walk to Lambert's Cove

StanleyRating, 5 stars8 months ago

my wife and i spent a thoroughly enjoyable week in late september in william's charming cottage on lambert's cove. even in when when it's grey and chilly outside, it's a comfortable and cheerful place to be. the large window in the living room affords a striking view of the james pond and the dunes separating it from lambert's cove. it's a short walk to the beach, with its crystal-clear water and golden sand.