Vacation rentals in Chilmark

An open living room features a large sectional sofa arranged around a coffee table. A stone fireplace is positioned against a brick wall, with warm wood beams overhead. Natural light floods the space through expansive windows, showcasing a wooden floor.

4.6 out of 5 average rating, 5 reviews

Private Chilmark Escape sleeps 6

Great retreat for a family/group in this light-filled private house w a spacious mahogany deck. Waskosim's Rock Res/passes to Lucy Vincent/Squibnocket- by presenting your lease at town hall. Tennis @ private assoc courts.Midcentury modern w all-wood cathedral ceilings. Open-floor-plan living room has huge sectional/Smart TV/Mini splits .All-new kitchen has natural soapstone countertops, Bosch fridge/dishwasher. In 2026 the entire interior was freshly painted and the carpeting downstairs is new.

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.

5 out of 5 average rating, 24 reviews

The Blueberry House on Martha’s Vineyard

Welcome to 'The Blueberry House' in Chilmark, up-island in beautiful Martha's Vineyard. This sweet private cottage is designer done with gorgeous furnishings, comfortable touches, and a nod to all things local. This 2 bedroom, 2 bath, 2 story home with outdoor shower will quickly find a place in your heart. Prime location off North Road next to North Tabor Farm with quick access to Great Rock Bight preserve, Menemsha Beach and Chilmark Store. Multi-week stays require weekly cleaning $300 each.

4.98 out of 5 average rating, 233 reviews

A bright sleeping area features a spacious white bed with decorative pillows and bedside lamps. A small kitchen area with light-colored cabinetry is visible in the background, complemented by a large window allowing natural light. A cozy seating area adds to the warmth of the space.

Guesthouse in Chilmark

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 and outdoor shower. A small kitchen features butcher block countertops, stainless steel sink, refrigerator and 2 burner electric stove and island. Air conditioning and heat. The space comes with a walk -on-pass to Lucy Vincent Beach.

An outdoor deck with a wooden dining table and matching chairs is shown, illuminated by a vibrant sunset. Lush greenery and the neighboring buildings can be seen in the background, creating a peaceful setting for dining al fresco.

4.98 out of 5 average rating, 43 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, 10 reviews

Cottage in Chilmark

Menemsha Cottage

Bell Buoy is lovely water view cottage with one bedroom, full bath, full kitchen, living room with wood burning fireplace,water view sun deck, screened porch and outdoor shower. Menemsha beach is just down the path and passes to a Chilmark's Private Beaches - Lucy Vincent or Squibnocket are included. Our guest have use of all of the inn's facilities including the gym , tennis court and paddle craft launch. A special feature is grilling dinner watching the setting sun drop into the sea.

Guest suite in West Tisbury

A spacious guest suite is illuminated by natural light from multiple skylights. The room includes a comfortable queen size bed with crisp linens, a sitting area with a light-colored couch, and a coffee table. Wood flooring adds warmth to the inviting atmosphere.

4.94 out of 5 average rating, 173 reviews

The Loft Guest Suite. Private. Newly Renovated.

This beautiful guest suite is a 5 minute walk to the village of West Tisbury on Martha’s Vineyard and has a private entrance on the 2nd floor of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this large 400 square foot suite has vaulted wood ceilings and skylights. Enjoy the outdoor shower and new outdoor sitting area. The location is centrally located, a short walk to a village, providing amenities. Ask about our other guest suites if you are with others.

A spacious living area features a large sectional sofa and a coffee table, creating a comfortable gathering spot. Light filters in through two large windows, illuminating the warm wood flooring. A dining area is visible in the background, and framed artwork decorates the walls.

4.85 out of 5 average rating, 68 reviews

Chilmark Cape in private wooded setting

A 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 wooded acres. Staying in Chilmark allows you access to the best beaches on the island. 2026 Season: Reminder that ferry tickets are the responsibility of the tenants. Our guests can obtain a sticker for access to Lucy Vincent Beach Pets permitted w/some restrictions.

4.99 out of 5 average rating, 110 reviews

The open living area features exposed wooden beams overhead and includes a spacious wooden dining table. Two lounge chairs, a round pouf, and a day bed are arranged for seating. Natural light filters in through large glass doors, leading to an outdoor area.

Guesthouse in Chilmark

4-Season Guest House on Historic Chilmark Estate

Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

4.97 out of 5 average rating, 58 reviews

A gravel driveway leads to a charming house with a red garage. A wooden pergola, adorned with greenery, provides shade along the entrance. Lush trees and open sky enhance the serene outdoor setting, inviting visitors to explore the surrounding landscape.

Home in West Tisbury

Vineyard Meadow Writer's Cottage with Hot Tub

This lovely retreat is just steps from miles of trails. Walk to the beach or meander through woods of Long Point Wildlife Refuge, experiencing the serenity of this untouched corner of Martha's Vineyard. After a day of enjoying the outdoors, come home to the light and airy writer's retreat. The HOT TUB IS OPEN! It also has an outdoor shower and a wonderful kitchen. This is the perfect location for a get-away with family and friends or for a creative retreat with your fellow artists.

A well-lit room features tall windows providing views of the outdoor deck. A wooden desk and chair are positioned next to a seating area, which includes an armchair and a floral-patterned chair. Bookshelves line the walls, and vibrant artwork decorates the space.

4.98 out of 5 average rating, 89 reviews

2 BR-Private guest house

Welcome to our charming 2-bedroom private guest house, nestled in a peaceful Chilmark neighborhood. Enjoy the spacious outdoor area, perfect for gatherings, featuring an 8-person dining set, a wood-burning fire pit, a BBQ grill and a seasonal outdoor shower. Our location offers easy access to local attractions: just a 4-minute drive to Alleys General Store, West Tisbury Center, and the library, and only 5 minutes to the stunning Lucy Vincent Beach and Chilmark town center.

Guesthouse in West Tisbury

A rustic studio cottage is presented with a sloped roof and blue siding. A wooden deck leads to the entrance, flanked by a garden with flower beds. A grill is visible on the deck, and a stone pathway meanders through the green yard.

5 out of 5 average rating, 39 reviews

Charming W. Tisbury Studio Guest Cottage

Charming rustic studio guest cottage with a private yard and outdoor shower, a perfect getaway. Walking distance to North Tisbury Farm and Market and State Road Restaurant and short ride to the small town of West Tisbury where you can check out Alley’s general store or get a great sandwich at 7a’s takeout. Ten minutes to Vineyard Haven and centrally located to all island destinations and many of the scenic Vineyard hiking trails.

4.92 out of 5 average rating, 64 reviews

The cottage presents a contemporary design with a light grey exterior and solar panels on the roof. A spacious deck is accessible by a set of steps, surrounded by lush greenery and landscaped areas. The sky is bright, enhancing the fresh and airy feel of the property.

Home in Aquinnah

Oceanview Beachwalk Cottage

Enjoy a spectacular view from this lovely clean, airy, minimalist, well outfitted cottage, on 3 private acres in walking distance to Lobsterville Beach, custom built with a contemporary twist, large deck, eco-green building, paint, granite and clean, simple design. Our enclosed outdoor shower is a feature you won't want to miss. It's such a pleasure to shower outside, you'll never want to use the indoor shower again.

Popular amenities for Chilmark vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Chilmark

The exterior of the renovated barn showcases a charming cottage-style design with gray shingle siding. A well-maintained lawn is surrounded by a variety of colorful flowers and shrubs, enhancing the natural setting. Large windows allow for ample natural light while adding character to the home.

4.99 out of 5 average rating, 106 reviews

Renovated Barn in Chilmark 3BR

4.63 out of 5 average rating, 54 reviews

A beach cottage showcases a wooden deck leading up to its exterior, featuring multiple windows and a blue trim. Surrounding greenery and sandy terrain create a natural setting. The entrance is visible, alongside a glimpse of parked vehicles in the background.

Cabin in Aquinnah

50s Cottage on Martha’s Vineyard w/Private beach

Guesthouse in West Tisbury

The exterior of the guesthouse is shown, featuring a charming facade with wooden shingles and a circular window. A welcoming porch is visible, equipped with two wicker chairs, inviting relaxation under clear blue skies.

5 out of 5 average rating, 9 reviews

Designer's Guesthouse, Lambert's Cove

4.74 out of 5 average rating, 31 reviews

An outdoor patio area is surrounded by lush gardens featuring blooming flowers and greenery. Two blue chairs are positioned near a table underneath a large umbrella, providing a shaded space for relaxation. The backdrop includes a well-maintained building with multiple glass doors.

Apartment in Aquinnah

Quiet & Serene in Aquinnah

An aerial view captures a sprawling green landscape with a home nestled beside Menemsha Pond. The water's surface reflects the soft hues of the sunset. Surrounding trees and open fields contribute to the area’s serene, secluded charm.

5 out of 5 average rating, 16 reviews

Secluded 3 bedroom home with private beach access

5 out of 5 average rating, 3 reviews

Charming North Road Retreat

An open living space is highlighted by a high, wood-paneled ceiling. Large glass doors provide an unobstructed view of the outdoors, while modern furnishings in soft hues, including a dark sofa and red armchairs, create a relaxed atmosphere. A rustic wooden coffee table sits centrally.

4.56 out of 5 average rating, 25 reviews

Mid-Century Gem with Private Pool & Ocean Views

A charming brick barn is nestled among lush green grass, with a large tree providing shade. A winding brick pathway leads to the entrance, framed by surrounding stone walls. Adirondack chairs are positioned invitingly nearby, enhancing the serene outdoor setting.