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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Guest favourite

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 favourite

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 favourite

Guesthouse in Tisbury

4.89 out of 5 average rating, 103 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).

Top Guest favourite

Guesthouse in Edgartown

5 out of 5 average rating, 16 reviews

Wedding RetreatTrails Golfing BikePath 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.

Superhost

Guesthouse in Edgartown

4.96 out of 5 average rating, 52 reviews

Quiet, Pet Friendly, Close to Edgartown and Oak Bl

This new construction home in Edgartown is fully equipped with all the modern amenities, plus an open floor plan and a finished basement. Smith Hollow is located at the back of a 2-acre lot in the quiet and picturesque Smith Hollow neighborhood. The house is just steps from the town bike path and directly on miles of hiking trails and public preserves. You are 2.9 miles from town, a 7-minute drive and a 13-minute bike ride. You are on the MVTA bus route. We use email to manage your stay

Top Guest favourite

Guesthouse in Chilmark

4.99 out of 5 average rating, 94 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, 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 favourite

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 favourite

Guesthouse in Falmouth

5 out of 5 average rating, 52 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 favourite

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.

Top Guest favourite

Guesthouse in Oak Bluffs

4.99 out of 5 average rating, 90 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.

Guest favourite

Guesthouse in West Tisbury

4.92 out of 5 average rating, 75 reviews

Spirit Water Retreat Cottage

This charming cottage is nestled in the woods near an organic garden, just a short distance to fresh water ponds and the beach. Enjoy your coffee on the private deck, make a fire in the fireplace if it's chilly, or use the time to rest and restore in natural beauty.