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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 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.

Mermaid’s Lair. Padanaram Village, So. Dartmouth

Kick back & relax in this calm & stylish cottage located directly on the bay in Padanaram Village. This cute and cozy artist’s home is well equipped and features a 30’ deck that overlooks a 180 degree view of the ocean. This adorable abode is within walking distance to shops, restaurants & the gorgeous Marina. Located 45 minutes from Newport RI and 60 minutes from Boston, makes this South Coast home, the perfect place to plan day trips from or to just hang and enjoy the million dollar view.

The Lobster Pot: Lake Tashmoo, beachfront

Welcome to The Lobster Pot, your cozy beach cottage on the tranquil shores of Martha's Vineyard. Nestled on the waterfront, this charming retreat is ideal for a paradise getaway. Wake up to the soothing sound of waves, enjoy panoramic ocean views from your private deck, and relax in the gentle sea breeze. With its inviting décor and relaxed ambiance, The Lobster Pot offers a perfect blend of relaxation and adventure. Savor fresh seafood, stroll along the sandy beach, or enjoy stunning sunsets.

Panoramic ocean views 100 ft above Cape Cod Bay

Our 5-bdrm Nantucket style beach house has a new kitchen & open living space, with a new deck, all overlooking the entire shoreline of Cape Cod Bay from a commanding perch atop a 100-foot bluff. Whales and seals can be seen from your deck. Located in a private community with its own rocky beach access about 5 min walk from the house where you can hunt for shells & observe the ocean wildlife. This beach is ideal for kayaking. Plymouth also boasts 4 of top 10 rated public golf courses in MA.

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.

Luxury Cottage on the Potowomut River 2bd/2b

The Cottage at The Grange is located on the peaceful Potowomut River. It is a beautiful and newly renovated 2 bedroom (king, 2 twin beds) / 2 full bath home with all the modern amenities and conveniences expected from a luxury short-term rental while maintaining the historic charm of this colonial estate. Cook a gourmet meal in the stocked kitchen or BBQ on the deck. Situated on 11 pristine acres enjoy private tennis/pickleball courts, kayak access to Greenwich Bay and much more!

The Fairview

Bring the whole family to this great place with lots of room for fun. Located at the end of a peninsula, This Dog friendly family get-away is surrounded by Fabulous Ocean Views with Amazing Sun Rises and Sunsets. Rustic 1980s era charm, Large upper great room with television and seating for the whole family. The home is not heated, nor is it air conditioned, but is surrounded by ocean on three sides which provide a delightful ocean breeze. It's a short walk to association beach.

Juniper Point Cottage With Ocean View

Charming Cape Cod cottage on a quiet semi-private road with beautiful views of Vineyard Sound. This inviting coastal retreat features 3 bedrooms, 2 private en-suite baths, 1 semi-private en-suite bath, a fully equipped kitchen, gas fireplace, cable TV, WiFi, and air conditioning. Relax on the second-floor deck with water views or enjoy outdoor dining on the patio with the BBQ grill. Conveniently located near the Martha’s Vineyard ferry, bus station, beaches, shops, and town.

Private Pond-side Cape Cod Home

Charming 2 bedroom home located on Flax Pond. Enjoy a private sandy beach and dock. Swim, kayak, fish, boat (trolling motors only) and just relax. Enjoy the home’s spacious deck with comfortable seating for the whole family complete with chiminea for late night fires. 2 levels of lodging with central air. 2 full bathrooms, kitchen, dining room and great room. Minutes away from town beaches, bike path, golf, and shopping. Parking for approximately 4 cars.

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!

Central location for your vacation

An apartment in a peaceful Raised Ranch! Your Martha’s Vineyard sanctuary. Centrally located from nearby Vineyard Haven, Oak Bluffs, Edgartown and West Tisbury. Beaches and trails in close proximity. 8 minutes away from ferry. Great for family vacation, Island explorations, work trips, hosting wedding guests, wellness retreat, or just a simple gateway, this home will compliment your Martha’s Vineyard experience.