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

The exterior of the barn features wooden double doors that provide access to the interior. A stone wall runs along the garden, accompanied by seating areas consisting of a picnic table and two chairs. Lush greenery surrounds the property, enhancing the secluded feel.

Guesthouse in Chilmark

4.95 out of 5 average rating, 91 reviews

Beautifully Renovated 1800s Chilmark Barn

Beautiful 2-story private barn in Chilmark on Martha's Vineyard. Secluded yet convenient. Perfect for a couple or a couple with older children (space not good for those with mobility issues). Downstairs living area, dining area, fridge, toaster, coffee maker, half bath -- shower is outside in the private garden. Loft-style sleeping area upstairs (2 private sections). 2 friendly labs and 5 chickens on premises. Walk to Chilmark Store, easy bus access. Walk-on pass to town beaches, no car pass

Guest favorite

A dining set composed of a rectangular table surrounded by four cushioned chairs is positioned on a brick patio. The furniture features a dark woven texture, complementing the serene outdoor setting. Natural sunlight filters through a nearby window, enhancing the inviting space.

Guesthouse in Edgartown

4.93 out of 5 average rating, 15 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

Guest favorite

A stony coastline is demonstrated where land meets water, with gentle waves lapping against the rocks. A vibrant sunset casts warm hues across the sky, reflecting on the water's surface. Lush, green grass borders the rocks, adding to the serene atmosphere.

Guesthouse in Falmouth

4.89 out of 5 average rating, 175 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

A charming studio cottage is nestled among lush greenery, with a shingled exterior and a sloped roof. A circular clock decorates the facade near a window. The surrounding walkway is made of red brick, leading up to a deck area, enhancing the peaceful woodland setting.

Guesthouse in Tisbury

4.9 out of 5 average rating, 105 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 favorite

A set of wooden steps leads to a bright red door, framed by wooden beams and natural greenery. The outdoor area features a lawn that blends with the surrounding landscape, creating a welcoming entrance to the studio.

Guesthouse in West Tisbury

4.96 out of 5 average rating, 74 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.

Top guest favorite

A tall lighthouse stands on the sandy shoreline, illuminated by the warm glow of the setting sun. Soft clouds reflect shades of orange and pink in the evening sky, while the calm water of the harbor gently laps at the shore.

Guesthouse in Edgartown

5 out of 5 average rating, 21 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.

Guest favorite

A porch area is depicted with several black rocking chairs arranged on wooden flooring. A cream-colored tote bag with 'CHILMARK' printed prominently sits on the floor beside the chairs, suggesting a relaxed atmosphere for outdoor enjoyment.

Guesthouse in Chilmark

4.98 out of 5 average rating, 216 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

The charming exterior of a two-story guesthouse is framed by lush green trees. A wooden fence provides privacy while flower boxes adorn the windows. A red container adds a pop of color to the entrance, complemented by a grassy area and stone pathway leading to the front door.

Guesthouse in Edgartown

4.91 out of 5 average rating, 87 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!

Top guest favorite

A scenic aerial view captures a tranquil bay dotted with sailboats, surrounded by lush greenery. The calm waters reflect the clear blue sky, while the coastline stretches along the horizon, presenting a serene and inviting atmosphere.

Guesthouse in Falmouth

5 out of 5 average rating, 53 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 Tisbury

4.97 out of 5 average rating, 77 reviews

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.

Guest favorite

A rustic studio cottage is presented with a sloped roof and blue siding. A wooden deck leads to the entrance, flanked by a garden with flower beds. A grill is visible on the deck, and a stone pathway meanders through the green yard.

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 favorite

A screened-in porch features a wicker couch adorned with soft pillows, providing a comfortable seating area. Natural light pours in through multiple windows, allowing views of the lush greenery outside. A wooden table and a single chair offer additional seating options.

Guesthouse in West Tisbury

5 out of 5 average rating, 77 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.