Holiday rentals in Aquinnah

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, 109 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, 103 reviews

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.

Guest house in Chilmark

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

4.98 out of 5 average rating, 245 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.

Guest house 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.

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.

5.0 out of 5 average rating, 28 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.

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, 50 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.

Guest favourite

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, in 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, and soak in the hot tub (May 1 to Jan 3). 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.

4.97 out of 5 average rating, 62 reviews

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, 73 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.

4.63 out of 5 average rating, 38 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.

Flat in Aquinnah

Quiet & Serene in Aquinnah

Fall asleep to the sounds of the waves. Unique 1000 sqft. 1st floor suite, surrounded by conservation lands and adjacent to the new 320 acre Squibnocket Pond Reservation. The suite consists of 2 elegantly furnished bedrooms and a large marble bathroom. Three sets of French doors open onto an expansive terrace with gardens. Larger bedroom has a beach stone fireplace with a wood stove. 12 minute walk to private beach. Owner occupied on 2nd floor. Charming and serene. Pet Friendly

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, 94 reviews

Peaceful Retreat Near Up-Island Beaches

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.

4.61 out of 5 average rating, 61 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

*THIS IS A STEP ABOVE CAMPING* The 1950s beach cabins location is priceless including 300ft of private beach, looking straight into the Vineyard Sound and the Elizabeth Islands. My is it gorgeous! *Please do not book this cabin if you are looking for a new modern recently built dwelling. This cabin was built in 1950 by one man, with minor cosmetic updates. 95% of this property is original and one of the last original cabins on Martha’s Vineyard.

A cozy living area showcases a large, comfortable sofa and a wooden coffee table, with a mounted map adding character to the space. Sunlight streams through multiple windows, illuminating the room's airy feel. A dining table is visible, suggesting a welcoming atmosphere for gatherings.

4.85 out of 5 average rating, 20 reviews

Evelyn's Menemsha Camp - Best Vineyard View

Evelyn's House on the hill overlooking Menemsha Beach is the classic Marthas Vineyard Beach Cottage. Evelyn Flanders built her " Camp"in 1909 where the views of Menemsha Harbor and famous sunsets would be about as good as it gets. It's the same today. With 2 bedrooms, 2 baths and a loft it's perfect beach base camp.. Take the path to Menemsha beach or your passes to Lucy Vincent. You are most welcome to bring one pet.

Guest favourite

A charming waterfront cottage is depicted, featuring a light gray shingle exterior and a welcoming entryway with wooden steps. The expansive ocean view is visible in the background, enhancing the serene landscape, with clear skies and greenery surrounding the property.