Guesthouse vacation rentals in Dukes County

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Top-rated guesthouse rentals in Dukes County

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guesthouse in Oak Bluffs

4.94 out of 5 average rating, 77 reviews

The Nest, Comfortable, Cozy and Convenient

The Nest is a private entranced guesthouse that is ideally located 1 mile walking distance to Oak Bluffs town, harbor, beaches and ferries(summer only) The Nest is a one bedroom cottage with a queen bed and a queen sized sofa bed in the living space and a private bathroom. The nest has a fully equipped kitchen, cable TV, internet, air conditioning, heat and is cozy and quiet. Come experience all that Martha's Vineyard has to offer. Comfort and convenience is waiting for all of you nesters!

Guest favorite

Guesthouse in Falmouth

4.89 out of 5 average rating, 174 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 favorite

Guesthouse in Edgartown

5 out of 5 average rating, 21 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.

Guest favorite

Guesthouse in West Tisbury

4.95 out of 5 average rating, 55 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 favorite

Guesthouse in Chilmark

4.99 out of 5 average rating, 92 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 favorite

Guesthouse in Chilmark

4.98 out of 5 average rating, 215 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.

Guest favorite

Guesthouse in Edgartown

4.9 out of 5 average rating, 83 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!

Guest favorite

Guesthouse in Falmouth

5 out of 5 average rating, 51 reviews

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

Guest favorite

Guesthouse in West Tisbury

5 out of 5 average rating, 24 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 favorite

Guesthouse in West Tisbury

5 out of 5 average rating, 74 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.

Guest favorite

Guesthouse in Oak Bluffs

4.99 out of 5 average rating, 88 reviews

Mermaid Cottage

Our735 square foot guest cottage is spacious and has a contemporary beachy feel. We are located near the ferries, buses, bike path and a short walk to a public beach. We've tried to provide everything you'll need for a comfortable stay on Martha's Vineyard. The house has a front porch, outdoor dining, hot tub and central air.