Guesthouse vacation rentals in Martha's Vineyard

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Popular amenities for Martha's Vineyard guesthouse rentals

Family-friendly guest house rentals

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 stars7 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!
Guest favorite
The exterior of a charming cottage displays a sloped roof with shingles and large windows, framed by lush greenery. An American flag is proudly displayed above the entrance, while colorful flowers and plants enhance the area in front of the house.
Guesthouse in Dennis
4.85 out of 5 average rating, 266 reviews

Joe's Beach Hideaway

SarahRating, 5 stars2 weeks ago
Joe’s place was perfect for our short little getaway! We had our dog, so much of what we did was go for walks, check out the beaches, explore the area, and get takeout. Joe was sure to provide us with many local recommendations. He was flexible with our check-in and provided clear instructions. He was also very responsive throughout our stay. The unit was very cozy and well appointed. I can only imagine how enjoyable it is in the warmer months! We hope to come back someday! Thanks again ☀️
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, 90 reviews

Mermaid Cottage

AngelaRating, 5 stars1 week 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 spacious backyard is visible, featuring a wooden deck attached to a charming guesthouse. Lush green grass surrounds the area, complemented by trees that provide shade. The exterior of the guesthouse displays light-colored siding and a brick chimney, enhancing the natural setting.
Guesthouse in Barnstable
4.9 out of 5 average rating, 59 reviews

Osterville Guest House

MonicaRating, 5 stars6 months ago
Truly enjoyed the space. It was right next to a lot of cute local shops. Would recommend!
Guest favorite
Guesthouse in Edgartown
4.74 out of 5 average rating, 47 reviews

Marthas Vineyard 1BR Cottage 10 min to beach/town

CarolRating, 5 stars7 months ago
Exactly as pictured! Had a wonderful week and can’t say enough about the magical outdoor shower. Enjoyed having my dog with me and convenience of walk to beach location. We walked into Edgartown every morning- using bike path. Lovely way to start the day. Would absolutely book again (and again)
Guest favorite
Guesthouse in Chilmark
4.94 out of 5 average rating, 90 reviews

Beautifully Renovated 1800s Chilmark Barn

TracyRating, 5 stars6 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!
Top guest favorite
A cozy sleeping area features a twin bed with a navy blue comforter and decorative pillow. A blue nightstand stands nearby, while a textured rug covers the warm wooden floor. The space is illuminated by natural light, creating a serene atmosphere.
Guesthouse in Nantucket
4.99 out of 5 average rating, 79 reviews

Beautiful Nantucket Summer rental

TracyRating, 5 stars7 months ago
Nadia’s home was the perfect setting for a 5 -star girls’ weekend on Nantucket! The outdoor shower was wonderful, the furniture was comfortable, and the home was cute and quintessentially Nantucket. There were beach umbrellas for shade, chairs to use for watching sunsets, and a small cooler to carry our chilled wine. The Wave stop was a 5 minute walk where we often spotted deer and rabbits as we walked to the shuttle. Finally, Nadia was a kind and responsive host. We found our Nantucket getaway spot and hope to be back soon!
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, 21 reviews

THE BIG CHILL ~ ONE MILE TO EDGARTOWN CENTER

JenniferRating, 5 stars5 months ago
Kati and her husband Mark were fantastic hosts! They were extremely friendly and helpful. The ‘Big Chill’ was just as nice in person as it was in pictures. It was clean and spacious and nice to have a downstairs area to hang out in and plenty of sleeping space upstairs. We could easily walk to the market for pastries, coffee and groceries and was an easy 5 minute drive to Edgartown . The surroundings were beautiful and we even saw deer and wild turkeys on the property! We would definitely stay there again!

Guest house rentals with a patio

Guest favorite
A brick patio is depicted, featuring a lounge chair and a small dining area with outdoor seating. A gas grill is visible, providing space for outdoor cooking. Surrounding greenery and trees create a natural, shaded ambiance, enhancing the outdoor experience.
Guesthouse in Edgartown
4.93 out of 5 average rating, 15 reviews

Private cabin in Wildlife Habitat; near bus route

ArthurRating, 5 stars7 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
4.96 out of 5 average rating, 28 reviews

Private Two bedroom Katama cottage near Edgartown

IlonaRating, 5 stars7 months ago
Great stay! Location was very good, central to everything but very private at the same time. Very nice host and really appreciated the goodies from Morning Glory Farm. Thank you!!
Guest favorite
The exterior of a newly constructed barn-style carriage house is shown, featuring a wooden deck with a railing. A single entrance door is located in the center, flanked by plants. The structure is surrounded by green lawns and trees, offering a tranquil setting.
Guesthouse in Sandwich
4.97 out of 5 average rating, 63 reviews

Private 1 king bedroom guest house-2021 built

ArtRating, 5 stars7 months ago
Most comfortable bed ever! The setting was beautiful, lush, green and relaxing. A perfect rejuvenation point for a busy Cape Cod sightseeing stay. The accommodations were well appointed. A great night sleep on a comfortable bed was a bonus!
Top guest favorite
A charming studio cottage is framed by lush greenery and mature trees, offering a welcoming entrance. A wraparound porch with seating invites relaxation, while a winding stone pathway leads to the outdoor space, enhancing the property's natural beauty.
Guesthouse in Bourne
5 out of 5 average rating, 65 reviews

Waterfront Cottage / Your Cape Escape

LisetteRating, 5 stars6 months ago
We really loved our stay! The place was adorable and we felt like the host went above and beyond what I’ve ever seen an Airbnb host do before. They had set aside a little snack basket and some gifts as well as personalized touches. Very clear instructions and lots of special extras (like a cabinet of frequently forgotten items plus first and even shower steamers). It very much felt like the hosts really cared and wanted us to have a wonderful stay!
Top guest favorite
The exterior of a charming duplex features a pathway lined with colorful shrubs and plants. A welcoming front porch leads to light-colored siding, with a blue door providing a pop of color. Adjacent to the entrance, a wooden trellis adds character to the outdoor space.
Guesthouse in Yarmouth
5 out of 5 average rating, 39 reviews

Cozy, renovated home in a charming duplex cottage

BarbaraRating, 5 stars4 months ago
Easy and responsive. The house was clean and well equipped.
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

StephenRating, 5 stars6 months ago
This cottage was perfect me, my wife, and our dog! We like the quieter side of Martha’s Vineyard and we found it here. You feel like you’re tucked away, but it’s easy to get to, and you are still within walking distance to a wonderful restaurant, and a short drive to anything else you need. You can get to the most beautiful beaches in just a few minutes. I am so appreciative that Adam was an extremely helpful host and very easy to communicate with. Would love to stay here again!
Top guest favorite
Guesthouse in Sandwich
5 out of 5 average rating, 15 reviews

the Elevated Escape

AnthonyRating, 5 stars7 months ago
Allison is a dream host. We stayed at the cottage for our engagement and proposal trip and couldn’t have picked a more perfect place for it. Allison created a magical Cape Cod experience full of beautiful details including fresh flowers, relaxing hammock, chill breakfast deck, whimsical treehouse, soft bedding and wonderful kitchen with views of nature. Everything is designed with fine taste and genuine care. Line of sights flow elegantly and framed beautiful views throughout the space. She left us handwritten notes and generously prepared the space for our engagement photoshoot. We had such a peaceful and romantic time at the cottage that it felt like a sweet home away from home. We left with lots of happy memories and inspirations. Thank you Allison. We truly loved the space and would come back again in a heartbeat!
Superhost
The exterior of a cottage is presented, featuring textured wooden siding in muted gray tones. Multiple windows allow natural light to enter, and a white front door adds contrast. A stone pathway leads to the entrance, surrounded by an open grassy area.
Guesthouse in Nantucket
4.85 out of 5 average rating, 27 reviews

Conveniently-located cottage with on-site parking

BonnieRating, 5 stars7 months ago
Lovely Nantucket cottage, very homey and sweet. John is a wealth of local information and very responsive. we really enjoyed our stay!

Guest house rentals with a washer and dryer

A serene view of a calm body of water reflecting the clear blue sky. A small sandy beach leads to a wooden dock, which extends into the water. A lone tree stands nearby, providing a touch of greenery to the peaceful scene.
Guesthouse in Yarmouth
4.87 out of 5 average rating, 15 reviews

Carriage house in historic district,walk to beach!

KumikoRating, 5 stars8 months ago
Christin was a gracious host and very responsive to our needs. The only thing I would have any complaints about is that it was a very hot week when we stayed and since there was only one AC upstairs where the two bedrooms are it was quite hot in the bedroom that didn’t have the AC. Other than that, the place was very charming and we very much enjoyed our stay
A charming cottage exterior features gray shingles and white trim. A bay window sits prominently on the left, surrounded by potted plants. The front door is centered and framed by two windows, under a small gabled roof, providing a welcoming entrance.
Guesthouse in Barnstable
4.86 out of 5 average rating, 86 reviews

Guest Cottage

KimberlyRating, 5 stars8 months ago
The place was spotless Tina thought of everything little extras that really helped make our stay more enjoyable. She stated the art appliances. Everything was upgraded. She was easily accessible if we had any questions I would highly recommend her place.😊 Kimberly salatino Queensbury, New York
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 stars6 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.
Guest favorite
A spacious artist's studio is illuminated by natural light from multiple skylights and windows. The layout includes a comfortable king bed and a work area with tables and chairs, creating an inviting space for creativity. Warm wood accents complement the bright, airy atmosphere.
Guesthouse in West Tisbury
4.96 out of 5 average rating, 67 reviews

Vineyard Meadow Artist Studio

RinaRating, 5 stars2 weeks ago
Carlo's place was centrally located on the Vineyard, just a short drive from the various towns! The house is located on the edge of a wild life refuge, and is a beautiful, two mile walk from the beach. The apartment itself is comfortable and has all the essentials.
Top guest favorite
A stone pathway leads towards the entrance of the property, bordered by lush greenery and well-maintained hedges. A wooden fence stands to the right, with an American flag gently waving in the breeze. Bright blue sky adds to the inviting ambiance.
Guesthouse in Tisbury
5 out of 5 average rating, 7 reviews

Escape to Bungalow 24 on MV!

AmyRating, 5 stars7 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 charming two-story casita is surrounded by lush greenery, featuring wooden siding and a gray roof. A gravel pathway leads to the entrance, bordered by low shrubs. Colorful prayer flags add a decorative element to the serene outdoor setting.
Guesthouse in Edgartown
5 out of 5 average rating, 29 reviews

La Casita

EliseRating, 5 stars31 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.
Superhost
A wooden gate opens to a private outdoor space, surrounded by tall trees and a stone-paved patio. The gate is constructed from matching wood to the house, blending seamlessly with the natural environment.
Guesthouse in Edgartown
4.96 out of 5 average rating, 52 reviews

Quiet, Pet Friendly, Close to Edgartown and Oak Bl

MatthewRating, 5 stars3 months ago
We had a great stay in the off season. The house was comfortable and clean.

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