Holiday houses in Dukes County

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.

The Abode 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 back wing of our newly renovated modern barn house. Surrounded by trees, beside a large meadow, this bright and airy 400 space has a sitting area and a full kitchen. Enjoy the outdoor shower and the outdoor sitting area. The location is centrally located and a short walk to a village, providing many amenities. Ask about our other guest suites if you are with others.

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.

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.

Luxury Guest Suite w/ Private Patio • Near Town

This apartment was newly built just a few years ago & still feels brand new. Located above the garage of our main residence, it has a private side entrance completely separate from the main house for total privacy. Set at the end of a beautiful subdivision just 2 miles from downtown Vineyard Haven, guests enjoy a private patio w/ gardens & a gas fire pit. Inside features stylish Vineyard décor, crisp A/C, fully equipped kitchen, large bedroom w/ queen memory foam bed & a large walk-in shower.

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.

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.

The Boat House

Located on majestic East Chop and only a mile and a half from both Vineyard Haven and Oak Bluffs, this rustic ocean front cottage offers a unique Martha's Vineyard experience. Whether you relax on the the private beach and watch majestic sunsets, stroll up to East Chop Lighthouse, or head only a little over a mile to vibrant Oak Bluffs harbor, you are sure to have a memorable trip. This is the perfect perfect haven from which to explore Martha's Vineyard.

The Luxury Vineyard Yurt

Discover this exceptional Luxury Yurt firsthand! Upon entering, you will be welcomed by a distinctive experience, featuring textured concrete radiant floors and a four-foot circular central skylight. Every aspect has been meticulously designed, allowing you to relax in a generous private yard. Enjoy your evenings under the stars, utilize the complimentary paddling, practice yoga in the spacious loft, and indulge in the beauty of your private island Yurt!

Beachfront Cottage w. Yard + Town Access

Welcome to The Mizzen Cottage! Updated 1930's cottage on an ocean front compound on beautiful Chappaquiddick. Complete with a picturesque porch overlooking the outer harbor, side deck, outdoor shower, washer/dryer, dishwasher. Stunning views of the Edgartown lighthouse and Cape Poge. Access to a private beach. Access town with just a 10 minute walk (or 1 minute drive) to the Chappaquiddick Ferry, and be in downtown Edgartown in 15 minutes or less!

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.

*NEW! Water Views | Falmouth Heights Beach

Welcome to your serene coastal escape! Forget the stress of long commutes to the shore; this beautifully updated and thoughtfully designed home is the perfect sanctuary for families or friends seeking a mix of relaxation and classic Cape Cod adventure. Tucked away in a quiet, friendly neighborhood, you are perfectly positioned to enjoy the best of Falmouth’s beaches and its vibrant downtown.