Guesthouse vacation rentals in Dukes County

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Popular amenities for Dukes County guesthouse rentals

Family-friendly guest house rentals

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
4.94 out of 5 average rating, 90 reviews

Beautifully Renovated 1800s Chilmark Barn

TracyRating, 5 stars7 months ago
Jessica was an amazing host! I’ve been talking with Jessica for about nine months in preparation of coming to stay here for my stepdaughter‘s wedding. She was so helpful so flexible she’s very informative. She loves living here, which makes it so much better to enjoy because she has so much knowledge about the island . The Property was beautiful andamazing! She’s an amazing host extremely hospitable and makes you feel so welcome. We will be coming back!
Guest favorite
The charming cottage exterior features a stone pathway leading to the entrance, surrounded by lush greenery and flowering bushes. A wooden gate provides access to the private yard, with a tranquil lawn area inviting relaxation.
Guesthouse in Vineyard Haven
4.94 out of 5 average rating, 126 reviews

West Chop Cottage + Beach Access

MichelleRating, 5 stars8 months ago
We had a great stay with Peggy! She is wonderfully kind and we had everything we needed to relax and adventure on the island. Such an amazing location and cute, cozy space, would highly recommend!
Top guest favorite
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.
Guesthouse in Edgartown
5 out of 5 average rating, 22 reviews

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER

AlmutRating, 5 stars2 weeks ago
We had wonderful days at Big Chill. The cottage and main house is located very privately in a wooded area and surrounded by a beautiful garden, creating a magical space in nature. The cottage is very beautiful, bright, clean and has most things you need.We liked especially the upper floor where all beds were in one spacious room The cottage is entirely designed and built with care and character, craftsmanship, an artistic eye, and much heart by the hosts Kati and Mark. And they are ,as well ,very caring about their guests. They enjoy having guests and helping them, which creates a unique place where we felt very well and being in the right place.Thank you for creating such a nice place and sharing it with all your guests.
Top guest favorite
A dining area is presented with a rustic wooden table, set for a meal. Four dark chairs surround the table, and a vase of white flowers adds a touch of decor. The adjacent living area features a comfortable sofa, flanked by windows allowing natural light.
Guesthouse in Oak Bluffs
4.99 out of 5 average rating, 91 reviews

Mermaid Cottage

AngelaRating, 5 stars1 month ago
What a perfect, cozy space to spend our long weekend on Martha’s Vineyard! This place is better than the pictures. Beautifully decorated, well stocked, comfortable bed, so quaint, and peaceful location. This is an easy drive to all towns on the island. It comfortably fit two adults and our infant. We would hands down return!
Guest favorite
A wooden gate opens to a lush garden, framed by tall greenery and vibrant flowers. A pathway made of stones leads through the garden, offering a welcoming entrance to the cottage. Sunlight highlights the natural beauty of the space on a clear day.
Guesthouse in Edgartown
4.76 out of 5 average rating, 49 reviews

Marthas Vineyard 1BR Cottage 10 min to beach/town

ThomasRating, 5 stars2 weeks ago
We really enjoyed our stay at this cottage. It was clean, comfortable, and close to town and the beach. Michael was an excellent host!

Guest house rentals with a patio

A charming guesthouse is framed by a well-maintained lawn and a large tree, which provides shade. The exterior features white siding with historical accents, and the windows are adorned with decorative elements. Soft lighting emanates from the interior, creating a welcoming ambiance.
Guesthouse in Edgartown
5 out of 5 average rating, 3 reviews

Beautiful Charming Edgartown Guesthouse 1 Bedroom

LizaRating, 5 stars11 months ago
It was a pleasure meeting Ronald and Gayle - they were fantastic hosts - very welcoming, polite, and friendly. We really enjoyed our stay in their adorable little guest house. The cottage is very quiet, clean, comfortable, modern, efficiently designed, and tastefully decorated. It has a lovely view of a manicured lawn and beautiful plantings. We hope to stay here again!
The exterior of the cottage is showcased, featuring a welcoming porch with hanging planters. Lush hydrangeas surround the entrance, complemented by a mix of greenery. The rustic red siding adds charm, and tall trees provide a natural backdrop, creating a serene environment.
Guesthouse in Edgartown
4.75 out of 5 average rating, 8 reviews

Mushroom Cottage

BillRating, 5 stars9 months ago
Great, cozy Martha’s Vineyard “studio.” Bikeable to Edgartown and Oak Bluffs. Bus stop nearby, but set back from road. I appreciated the powerful A/C during a really hot and humid week.
Guest favorite
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.
Guesthouse in Edgartown
4.93 out of 5 average rating, 15 reviews

Private cabin in Wildlife Habitat; near bus route

ArthurRating, 5 stars9 months ago
As long as you don't mind having only an outdoor shower,which I didn't since the weather was beautiful, Judys place is a nice quiet cozy nook surrounded by lovely well kept grounds. Total privacy. Judy was a very attentive host, allways checking in via emailand offering to go beyond what I expected.
Top guest favorite
A private deck is framed by lush greenery, featuring two wicker chairs and a small table. The entrance is marked by glass doors that open to the cottage, with light filtering through the surrounding foliage.
Guesthouse in Edgartown
4.97 out of 5 average rating, 29 reviews

Private Two bedroom Katama cottage near Edgartown

MeganRating, 5 stars5 days ago
Our stay in Martha’s Vineyard was perfect. The Clamshell was beautifully decorated and was extremely clean - even better than the pictures. The location is outstanding and made it easy to come and go. We felt right at home during our visit. Nancy’s hospitality is unmatched.
A coastal landscape features a gently curving shoreline with sandy beaches and rocky outcrops. The cliffs are adorned with light-colored layers, contrasting with the deep blue of the ocean. Lush greenery is visible along the coastline, complementing the tranquil seascape under a partly cloudy sky.
Guesthouse in Oak Bluffs

Fantastical Fishermen’s Cottage & private Garden

HanleyRating, 5 stars22 months ago
A beautiful place in a lovely setting! We would definitely come back here again on our next visit to the Vineyard. Carolyn is one of the most responsive and helpful hosts we've had. A truly great stay.
Top guest favorite
An open living area is highlighted by high ceilings with exposed beams and large glass doors that provide a view of the meadow. Two comfortable sofas face each other across a central area rug, inviting relaxation. Light floods the space, enhancing its airy feel.
Guesthouse in West Tisbury
5 out of 5 average rating, 11 reviews

Beautiful + Airy MV Barn

LolaRating, 5 stars8 months ago
Our second time at the barn! Heaven. An absolute dream. Comfortable, quiet, clean and well appointed. We shall return. Thanks so much Amy.
A quaint cottage features shingle siding and a peaked roof. Sunlight filters through the trees, illuminating large windows adorned with flower boxes. An inviting adirondack chair and a small stool are positioned on the wooden deck, creating a serene outdoor seating area.
Guesthouse in Falmouth
New place to stay

Woods Hole Backyard Guest House Full of charm!

Guest house rentals with a washer and dryer

Superhost
A welcoming porch is displayed with two white rocking chairs and a small side table on a wooden floor. Natural light filters through the nearby windows, and a door with a dark green finish is visible in the background. The surrounding greenery adds a serene touch.
Guesthouse in Edgartown
4.96 out of 5 average rating, 53 reviews

Quiet, Pet Friendly, Close to Edgartown and Oak Bl

SeanRating, 5 stars2 weeks ago
Worth it, totally lived up to our hopes and expectations. Great house, perfect for a family (+dog) and was situated perfectly to get anywhere on the island. We had a wonderful time.
A charming cottage is framed by vibrant gardens filled with blooming flowers in various hues. The building features a sloped roof and is surrounded by lush greenery, adding a serene touch to the overall setting.
Guesthouse in Edgartown
4.91 out of 5 average rating, 11 reviews

Beautiful Cottage in Private but Convenient Locale

DaveRating, 5 stars24 months ago
Rachel’s cottage is quite charming. Edgartown is easily accessible, yet the cottage is very private, ideal for a quiet getaway.
A well-maintained yard features a vast expanse of lush green grass, bordered by neatly arranged stone pathways. Flower beds, formed into heart shapes, display a variety of colorful blooms. A quaint two-story guesthouse can be seen in the background, surrounded by mature trees.
Guesthouse in Edgartown
5 out of 5 average rating, 18 reviews

Guesthouse

LeahRating, 5 stars8 months ago
My family and I had a wonderful stay at Dilcelia and Marquissuel's Airbnb. The place was extremely clean and the yard was an added bonus! They were extremely responsive to all of our needs and a delight to work with. I would definitely recommend the property to anyone looking to stay on Martha's Vineyard.
Superhost
A serene beach scene is presented, featuring gentle waves lapping at the sandy shore. The sky is adorned with a mix of soft clouds, creating a calm atmosphere. The shoreline's curvature leads the eye toward the distant land, enhancing the tranquil coastal setting.
Guesthouse in Falmouth
4.67 out of 5 average rating, 15 reviews

Woods Hole Cottage close to Beach and Village

KyleRating, 5 stars10 months ago
What a perfect little airbnb! This was the second year in a row that my wife and I stayed here with our toddler-aged daughter. I don't have much else to add beyond my review of last year other than everything was the same again in all the best ways. We did learn it's better, and easier, to take the bike path into town, accessing it via a path on the side of the cemetery behind the church. Once again, the owners were super kind and friendly. The place has even been upgraded in the past year with improved furniture and washer and dryer. A+++, would definitely recommend.
A wooden deck extends from the upper level of the house, featuring a shaded umbrella. Sturdy stairs lead up to the deck, while a gravel pathway surrounds the property. The exterior showcases natural wood siding and is nestled among trees, enhancing the secluded atmosphere.
Guesthouse in West Tisbury
4.94 out of 5 average rating, 18 reviews

Guest house over Garage

Michelle And GregRating, 5 stars8 months ago
Joe’s place was wonderful private and very well appointed. Highly recommended for a getaway in a lovely neighborhood. You can also put on a light backpack and hike down to the beach, which is a short hike. Please tell them that Greg sent you.
Top guest favorite
A bright entryway features a white dresser with multiple drawers, complemented by a lamp and a small vase of blue flowers. Natural light filters through two windows, illuminating the space and enhancing the clean, simple design. A staircase leads to the upper level.
Guesthouse in Tisbury
5 out of 5 average rating, 7 reviews

Escape to Bungalow 24 on MV!

AmyRating, 5 stars8 months ago
Steve was a great host. He immediately responded to get us out of a jam in short notice. He was very communicative. Place was new & updated. Modern beach feel. Great layout & convenient location (we normally stay in Chilmark & this was much closer to everything). It was perfect for us to unwind after some stressful weeks.
Superhost
A wooden sliding barn door with natural grain is captured. The door features a black metal track and hardware. In the background, the outline of a bathroom is visible, including a mirror and partially seen sink area, suggesting a harmonious blend of rustic and modern design.
Guesthouse in Edgartown
5 out of 5 average rating, 29 reviews

La Casita

EliseRating, 5 stars32 months ago
Lovely home, well-maintained and quiet. A beautiful place to rest as well as easy access to bike trails and towns. We used the outside shower the whole time and it was so refreshing. Had an incredible dinner at Lambert’s Cove in the garden.
A sandy beach scene is depicted, featuring large rocks scattered across the shoreline. Waves gently roll in under a partly cloudy sky, with dramatic clouds casting shadows. A person is seen climbing a rock, while another gestures towards the water, highlighting an inviting atmosphere.
Guesthouse in West Tisbury

Bright Summer Cottage

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