Orlofseignir í Aquinnah

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

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.

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.

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.

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.

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.

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

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.

Mink Cove Treehouse

A unique adult adventure awaits in this cozy hand crafted tree house! Nestled 12 feet off the ground amongst the chirping birds, red oaks & breathtaking views of Mink Cove in Buzzards Bay. The tree house is accessible by a suspension bridge that leads you to a partially covered porch where you can enjoy a cup of coffee or sit back & take in the sunset with a glass of wine. Step inside to the living space & snuggle up on the couch for an intimate evening.

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.

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.

Cozy Waterfront Cottage, Newly Remodeled!

Beautifully upgraded WATERFRONT cottage in Menemsha with (essentially a) PRIVATE BEACH! Direct access to Vineyard Sound from your own staircase leading down to the water’s edge. Enjoy stunning sunsets and breathtaking views from every room. Private and peaceful but conveniently located just a short drive or bike ride to Menemsha or the Chilmark village center.