Guesthouse vacation rentals in Dukes County

A patio dining area is set with a glass table and four wicker chairs. A bottle of wine stands at the center, accompanied by two glasses and two plates. Surrounding greenery creates a natural backdrop, enhancing the serene outdoor dining experience.

4.95 out of 5 average rating, 21 reviews

Private cabin in Wildlife Habitat; near bus route

Come to “Simple Sea-Renity”, a private cabin on Martha's Vineyard. Located in a half acre certified wildlife habitat, this air conditioned cabin offers lots of privacy while keeping your stay simple & back-to nature. You have your own small yard & a patio for dining, napping or stargazing -enclosed outdoor shower (toilet is indoors) -TV -wifi -gas grill -scullery sink -refrigerator/freezer -microwave -coffee maker Centrally-located in Edgartown, an easy walk to Sengekontacket or VTA routes

4.89 out of 5 average rating, 182 reviews

A quaint cottage exterior is surrounded by lush greenery and vibrant flower beds. The building features a shingled façade, a prominent chimney, and multiple windows, providing a welcoming appearance. A pathway leads to the front door, framed by colorful plants, enhancing the inviting ambiance.

Guesthouse in Falmouth

Quaint Cape Cod Cottage

Quaint cottage on Cape Cod, perfect for a last minute getaway. Amazing location with the beach, Shining Sea Bike Path, The Knob, and Spohr Gardens all within WALKING DISTANCE! A five minute drive to Falmouth Main Street which offers amazing restaurants and shops. In the other direction, another five minute drive will bring you to the historical seaside village of Woods Hole, home to world renowned scientists, numerous beaches, restaurants, museums, an aquarium and the Martha's Vineyard Ferry.

A bright living area features a comfortable seating arrangement with soft, neutral-toned couches. Natural light fills the space through multiple windows, and a rustic wooden coffee table enhances the cozy feel. A small dining area is visible in the background.

5 out of 5 average rating, 22 reviews

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER

The Big Chill is close to the buses, grocery stores, fish markets, Morning Glory Farm, the beautiful beaches and the center of Edgartown. You’ll love it.. its cozy, has A/C, you'll love the high ceilings on the second floor and the location! The BIG CHILL has a full bath indoors and a fully enclosed outdoor shower steps from the door. Great for couples, solo adventurers, and business travelers….a bike ride to town. If you need a bigger house, check out Sandy Feet Retreat for 5-10 guests.

4.9 out of 5 average rating, 109 reviews

The guest cottage is nestled among lush greenery, featuring a wooden deck that invites outdoor relaxation. Glass doors provide access to the interior, while a small dining set under a green umbrella enhances the inviting outdoor space.

Guesthouse in Tisbury

Martha's Vineyard Studio Cottage, walk to Lagoon!

This is a studio, guest cottage on a quiet woodland property, 1/4 mile from the main road (Edgartown/Vineyard Haven Road) and VTA bus service. A short walk to the Lagoon (5 min), Vineyard Haven (shopping, ferries), The Manuel F. Correllus State Forest (bike path), The YMCA of MV (day passes avail), The MVRH Performing Arts Center (concerts/performances), 10 minute drive to local beaches (Bend-In-The-Road Beach, Oak Bluffs / Joseph Sylvia State Beach, Edgartown / Beach Road, Vineyard Haven).

Guesthouse in West Tisbury

An open studio layout is showcased, featuring a spacious bed with a metal frame. A cozy seating area is arranged with patterned cushions and a wooden coffee table. Natural light pours in through multiple windows, illuminating the warm wood flooring and inviting ambiance.

4.96 out of 5 average rating, 78 reviews

Vineyard Meadow Artist Studio

This lovely artist's studio is just steps from miles of trails. Walk to the beach or meander through the woods of Long Point Wildlife Refuge, experiencing the serenity of this still untouched corner of Martha's Vineyard. This studio includes a bathroom with a shower, a washer/dryer and a kitchenette. It is the perfect spot for a lone artist, a couple or a family to enjoy Martha's Vineyard any time of year. This property shares the driveway and parking with Vineyard Meadows Writer's Cottage.

A well-lit bedroom features a spacious bed with white linens and decorative pillows. Natural light enters through two windows adorned with blinds. A soft area rug is positioned under the bed, complementing a cozy reading nook with a rattan chair and a bean bag.

5 out of 5 average rating, 31 reviews

Wedding RetreatTrails Golfing Beaches Private Gem

✨ LOCATION, LOCATION✨ ✅Cleanliness, Fully stocked kitchen ✅Pet-Friendly, Minutes from ferry & beaches ✅ Peaceful & private neighborhood 🌳 Hidden trails—Great for exploring 🏡 Perfectly Getaway, ✅ Easy access to all towns, Hassle-free stay. 🚗 Just 8 minutes to local markets, and top-rated restaurants. 🚴‍♂️ A scenic 13-minute bike ride takes you to the charming Edgartown Village or Katama South Beach—perfect for breathtaking sunsets! Convenience, comfort, and nature at your doorstep.

4.99 out of 5 average rating, 99 reviews

The open living area features exposed wooden beams overhead and includes a spacious wooden dining table. Two lounge chairs, a round pouf, and a day bed are arranged for seating. Natural light filters in through large glass doors, leading to an outdoor area.

Guesthouse in Chilmark

4-Season Guest House on Historic Chilmark Estate

Beautiful private guest house in Chilmark on Martha's Vineyard. Secluded yet convenient. Drive on pass to spectacular Chilmark beaches! Newly renovated and gorgeous. Great location - 10 minute walk to Chilmark Store. Full kitchen, living area, kitchen island/dining table, queen bed, day bed (not for sleeping), fireplace/heater, private outdoor shower, deck and picnic table, full bath inside. Keurig machine. 2 friendly labs/2 chickens on premises. Easy bus access. Old-style MV charm.

4.98 out of 5 average rating, 223 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.

Guesthouse 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 in addition to a private outdoor shower. A small kitchen features butcher block countertops, a stainless steel sink, refrigerator and electric stove. Central air conditioning + heat make it the perfect getaway for all seasons.

The interior features a wooden wall with a triangular peak highlighted by a small window, allowing natural light to filter through. A pendant light hangs from the ceiling, complementing the rustic aesthetics of the space.

4.92 out of 5 average rating, 98 reviews

Martha’s Vineyard Cottage - A Glamping Experience!

This is your vineyard home, where you can walk or ride a bike less than a mile to the beach or two into town. Get the glamping experience with kitchenette, A/C, an outdoor shower, a composting toilet, a queen bed in the loft and futon couch that can sleep two more in the living room. Enjoy outdoor games, outdoor seating, a Weber grill for bbq, tv, WiFi, cozy indoor space and more, right on the bike path with a bus stop for easy accessibility or free car parking. Whatever you want!

5 out of 5 average rating, 59 reviews

The exterior of a spacious cottage is displayed, framed by vibrant green lawns and seasonal flowers. A stone pathway leads up to the entrance, with pumpkins placed decoratively in the garden area. The clear blue sky enhances the overall inviting presence of the home.

Guesthouse in Falmouth

Falmouth/Woods Hole Charming Cottage By the Sea

Welcome to our Cottage By The Sea Rental located only minutes from the quaint village of Woods Hole, Falmouth and the Martha's Vineyard Ferry. We are located in the perfect setting to relax and enjoy all the area has to offer. Come enjoy The Shining Sea Bike path which is 10.7 miles , Sandy beaches, lively restaurants & local music scene, shopping on historic Main Street, Farmers Markets & more. Your sure to fall in Love with " Ole Cape Cod " when you visit our home and area

4.96 out of 5 average rating, 82 reviews

A scenic view is captured showcasing a vibrant sunset over the water, with sailboats gently floating. The sky displays rich hues of orange and pink, reflecting on the calm surface, creating a serene atmosphere.

Guesthouse in Tisbury

King bed, Water Views,AC,Near Bike Path- Bus stop

Have your morning coffee looking out at the sunrise and sailboats from your living room or bedroom windows. This modern studio feels secluded while only a mile and a half from Main Street Vineyard Haven, four miles from Oak Bluffs, and eight miles to Edgartown. This is the perfect place to unplug but does come equipped with everything you need, including wifi, smart tv, fully equipped kitchen, beach towels, linens, and bath towels for your stay.