Pet-friendly vacation rentals in Dukes County

Absolute Best Location on the Island

Ideal location for visitors in the middle of the most lively, diverse, fun town on Martha's Vineyard. This property is certified by the United States Department of Interior as a National Historic Property. The ferry terminal, restaurants, shops, markets, harbor, historic sites, entertainment, public transportation, and a clean sandy beach are all within minutes. A vehicle is not necessary. IF UNAVAILABLE: SIMILAR WALKABLE SISTER PROPERTY in Vineyard Haven: https://www.airbnb.com/rooms/49016488?

Lambert's Cove, Water view, Beach pass, Ferry Tix

Enjoy stunning views of Vineyard Sound from this cozy three bedroom two bath home in a quiet neighborhood just minutes from Lambert's Cove Beach. This upside down house has one bedroom on the main level along with a full bath and open kitchen, dining, and family room. The downstairs has another living space, two bedrooms, laundry room, and full bath. Enjoy family time in the open upstairs with water views, or retreat to the lower level living room for some separation, quiet time, or work space.

Secluded Up Island Cottage

Charming Martha's Vineyard post and beam house on two secluded acres with two bedrooms in West Tisbury. The master bedroom has a queen bed, the second bedroom has a full bed, the loft has a full size futon. It is peacefully tucked away at the end of a road with only three other houses on it. It has easy access to beaches, bike paths and walking trails. Enjoy some family time in the wooded backyard grilling or relaxing with an outdoor shower or napping in the hammock after a day at the beach.

2 BR-Private guest house with Hot Tub and Fire Pit

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, a 6-person hot tub, 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.

impeccable cottage STEPS to downtown OB & beach!

Unique opportunity to stay in an impeccable cottage in Downtown Oak Bluffs. With a front porch with rocking chairs, a back deck & grill, & an outdoor shower, and A/C! - this is the ideal oasis for your Vineyard Vacation. Turn right and find yourself steps from restaurants & shops on Circuit ave. Turn left and walk 5 mins to beautiful beaches. Everything you want out of vacation at your fingertips. Relax, and truly experience the Vineyard the way it was meant to be, at the @WeePackemInn

Waterview, Private, Walk to Beach, Mile to Town

Rustic barn-style home, waterview, spacious natural landscape, serenity, and privacy on 3 acres centrally located 1 mi from Oak Bluffs and Vineyard Haven centers. Walk to beach, bike path nearby, comfortable interiors, memory foam mattresses, cotton linens, 2 HDTVs, high-speed wifi, heat/AC, 2 ocean kayaks, and 2 bikes. Location, amenities and privacy surrounded by natural beauty make staying very easy and relaxing. Ask the host about ferry reservations if they appear to be sold out!

Beachfront Cottage + Studio w. Town Access

Welcome to The Rudder Cottage! Fully renovated 1930's cottage on an ocean front compound, with a picturesque porch overlooking the outer harbor, full basement with washer/dryer and central air. An additional detached studio provides a third bedroom/work space. Stunning views of the Edgartown lighthouse and Cape Poge. Access to 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!

Beautiful and walk to everything Oak Bluffs!

This is a beautiful cottage in the heart of Oak Bluffs! Walk to town, the inkwell beach and the harbor! This modern and comfortable space will be the perfect home base for you and your family. Enjoy all the amenities including central air. Coffee maker, full laundry, outdoor shower and a beautiful patio too. We are on property eager to make your stay as magical as possible. Please check the reviews of our other listings to see how guests enjoy our properties.

Ferry (Car) Reservations Available for Summer 2026

F͟R͟E͟E͟ ͟C͟A͟R͟ ͟F͟E͟R͟R͟Y͟ ͟R͟E͟S͟E͟R͟V͟A͟T͟I͟O͟N͟ ͟F͟O͟R͟ ͟A͟U͟G͟U͟S͟T͟ ͟2͟2͟-͟2͟9͟!͟ In town, 1930's cottage, lovingly updated by architect-owner. • Stylish decor, open floor plan, granite terrace • 2 blocks to Main St/harbor/ferry/town beach/playhouse • Central Air • Close to bike rentals, restaurants, shops, spa, library, mini-golf, etc. • Large yard with wood/gas grills, bocce, corn hole, beach chairs, fire pit • Outdoor shower • 3BR + sleeping loft

Edgartown Cottage By The Pond

Recently renovated cottage which is centrally located to everything the island has to offer. Located just 3 miles from downtown Edgartown, a 30 yard walk to Sengekontacket Pond and 1/4 mile to the bike path. The house has central air conditioning and lightning fast internet access The cottage is located on a 1/4 acre lot just steps from the pond and only a 1/4 walk to the entrance of Felix Neck Wildlife Sanctuary which is part of the Mass Audubon.

Charming Falmouth Heights Steps to Beach

Prime location in Falmouth Heights!!! Steps from beloved Falmouth Heights beach, the Black Dog Café, Shipwrecked, and the finish line to the Falmouth Road Race! We are also a short walk to the Island Queen Ferry to Martha’s Vineyard, the Falmouth Yacht Club, and the delights of Falmouth’s marvelous Main Street!

Quaint cottage near beach

**** 65./night is fall winter price*** *** 230./night Mat 30th spring summer price """ message direct will manually book Location, location, location.. One bedroom cottage recently renovated sleeps four, mere feet from a Nature reserve. Less than a quarter-mile from beautiful beach.