Guesthouse holiday rentals in Dukes County

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Top-rated Guesthouses in Dukes County

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Superhost

Guesthouse in Falmouth

4.88 out of 5 average rating, 154 reviews

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.

Guest favourite

Guesthouse in Edgartown

5.0 out of 5 average rating, 11 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.

Superhost

Guesthouse in Tisbury

4.89 out of 5 average rating, 92 reviews

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).

Guest favourite

Guesthouse in West Tisbury

5.0 out of 5 average rating, 26 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.

Guest favourite

Guesthouse in Chilmark

4.99 out of 5 average rating, 79 reviews

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.

Guest favourite

Guesthouse in Chilmark

4.98 out of 5 average rating, 198 reviews

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.

Superhost

Guesthouse in Edgartown

4.87 out of 5 average rating, 60 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!

Superhost

Guesthouse in Edgartown

4.97 out of 5 average rating, 35 reviews

Quiet, Pet Friendly, Close to Edgartown and Oak Bl

Newly completed in 2020, this new construction home in Edgartown is fully equipped with all the modern amenities and an open floor plan. The property is located at the back of a 2-acre lot in the quiet and picturesque Smith Hollow neighborhood. The house is located just steps from the town bike path, and directly on miles of hiking trails and public preserves. You are 2.9 miles from Edgartown which is a 7-minute drive and a 13-minute bike ride. You are also on the MVTA bus route.

Guest favourite

Guesthouse in Oak Bluffs

5.0 out of 5 average rating, 49 reviews

Coastal Bungalow

Discover this newly renovated property located just minutes from downtown on the Lagoon. The rental sits separately behind the main house in what once held a media room, lovingly converted to an open concept guest suite with queen bed, kitchenette, bath, and living space with convertible sleeper sofa. USB charging bedside lamps are some of the amenities offered. Accommodates 2 guests and possible 1-2 children. Private beach access on the Lagoon and 5 minutes from town.

Guest favourite

Guesthouse in West Tisbury

5.0 out of 5 average rating, 13 reviews

Charming W. Tisbury Studio Guest Cottage

Charming rustic studio guest cottage with a private yard and outdoor shower, a perfect getaway. Walking distance to North Tisbury Farm and Market and State Road Restaurant and short ride to the small town of West Tisbury where you can check out Alley’s general store or get a great sandwich at 7a’s takeout. Ten minutes to Vineyard Haven and centrally located to all island destinations and many of the scenic Vineyard hiking trails. Access to West Tisbury town beaches.

Guest favourite

Guesthouse in Tisbury

5.0 out of 5 average rating, 49 reviews

King bed, Private Entrance, Water Views, AC

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.

Guest favourite

Guesthouse in West Tisbury

5.0 out of 5 average rating, 51 reviews

Country cottage walk to Alley's General Store

This sunlit summery cottage is in a very quiet, private and pastoral setting, situated 100 feet from the small Tiasquam River, with many birds chirping in the abundant vegetation and trees nearby. Because of the river's proximity, the cottage has a Composting Toilet. My wife and I live on the property uphill from the cottage. The property is in the countryside but a 5 minute walk to the local town center.