Vacation rentals with outdoor seating in Chilmark

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Chilmark outdoor seating rentals

House rentals with outdoor seating

Guest favorite
Home in Yarmouth
5 out of 5 average rating, 13 reviews

Cozy Beach Cottage By The Sea

LeslieRating, 5 stars7 months ago
Absolutely adored this home and will certainly be back! Home was extremely clean and walking distance to the beach, even with toddlers. Excellent restaurants and so much to do locally! Hosts were very accommodating and responded immediately with anything asked! 10/10!
Guest favorite
A spacious deck offering unobstructed views of the Westport River features comfortable outdoor seating and a storage bench. The light-colored wooden flooring complements the soft hues of the house’s exterior, while nearby trees provide a natural backdrop.
Home in Westport
4.96 out of 5 average rating, 27 reviews

Riverhouse

WendyRating, 5 stars3 months ago
This was the perfect place for three friends who write and workshop together online to gather in person. The main room of the house is filled with light and what I didn't realize from the listing is the beautiful view from the living/dining room down to the river. The kitchen is well supplied and every room was very clean and uncluttered. The three bedrooms on the first floor are all very nice, with good beds and pillows (one is slightly larger with a king-sized bed), so we were able to decide on our rooms painlessly and none of us had to settle for an inferior room. The large dining table was perfect for spreading out our work as well as for dining, and one of us enjoyed having the furnished basement as her private work space. When we had a problem with hearing a beeping noise, which we initially thought might be a smoke detector battery that needed replacing, Bob was very responsive and helpful in figuring out the cause of the beeping from a motion detector. We plan to come again.
Guest favorite
The exterior of the contemporary home is depicted, featuring a natural wooden facade. A large red umbrella shades the deck, and multiple windows reflect the surrounding greenery. Steps lead up to the entrance, with well-maintained landscaping visible in the yard.
Home in Edgartown
4.88 out of 5 average rating, 26 reviews

FREE FERRY Car RESV July WK Game room Central AC

Lyons Rating, 5 stars6 months ago
We had a wonderful ti.e staying here. The house is beautiful and accommodated everyone. There is plenty to do in the area and was a nice central aarea to take in everything the island has to offer. We would love to sstay here again. Thank you so much for hhosting us!
Guest favorite
A bright living room features large windows offering views of the beach. Light-colored furnishings are complemented by a patterned area rug. A coffee table is centrally positioned, with decorative items placed atop. Two chairs provide additional seating, enhancing the open space.
Home in Fairhaven
4.93 out of 5 average rating, 29 reviews

Lovely Day Oceanside

BethRating, 5 stars5 days ago
Great home-base for day trips to places such as the Cape & Plymouth. Really serene location & awesome view. We liked some of the modern updates but also appreciated how “Lovely Day” has kept some of it’s 1950’s flair & uniqueness.
Superhost
The exterior of the home is presented at dusk, featuring soft outdoor lighting and classic blue siding. A pathway of stone leads to the entrance, flanked by neatly manicured shrubs and a lawn. A small porch area and steps provide access to the front door.
Home in Marstons Mills
4.88 out of 5 average rating, 133 reviews

The Mills Retreat- 3BR/2Bath - Beach pass included

JulieRating, 5 stars3 months ago
This was a family Christmas getaway, and it was perfect.
Guest favorite
A bright entryway features a sleek windowed door, allowing natural light to fill the space. Decorative planters stand beside the staircase, adding a touch of greenery. A console table holds neatly folded towels and a magazine, enhancing the clean, modern aesthetic of the area.
Home in West Barnstable
4.9 out of 5 average rating, 21 reviews

Haven on the hill

KaileyRating, 5 stars8 months ago
Marina’s home is so beautiful and clean! We had a crowd of couples and singles, the space fit everyone perfectly! Ample bathrooms, space for relaxing, and comfortable beds! We hope to be welcomed back.
Guest favorite
A charming single-story house is surrounded by well-maintained gardens featuring colorful hydrangeas and tidy shrubbery. A private driveway is visible alongside the house, complemented by a rustic wooden fence that adds to the property's warmth. The front entrance is framed by seasonal blooms.
Home in Dennis Port
4.96 out of 5 average rating, 68 reviews

Quaint Cape Beach House

SamanthaRating, 5 stars3 months ago
The house was cozy, quaint, and spotless—perfect for our off-season weekend getaway! Adele was incredibly accommodating and flexible with us, and her communication was top-tier. We couldn’t have asked for a better experience and would happily stay again. Highly recommend!
Guest favorite
A stone pathway leads up to the side of a house, bordered by green grass and plants. The two-story structure features a textured wooden exterior and multiple windows. Natural light illuminates the scene under a clear blue sky.
Home in Westport
4.85 out of 5 average rating, 105 reviews

Beach Home – Family Friendly - Solar Powered

SamuelRating, 5 stars4 months ago
This is like the 4th time we have stayed in this house ass we do quite a bit of work in the area. We love this place and this has been and will always be our 1st pick of the area Thank you Ciara for a Fantastic house and for being a wonderful Host

Apartment rentals with outdoor seating

Superhost
A cozy sitting area is showcased with two turquoise chairs and a small round table. Wooden beams accentuate the ceiling, while a colorful painting adds character to the wall. One chair features a reclined cushion, complemented by a lamp on each side table.
Apartment in Oak Bluffs
4.88 out of 5 average rating, 153 reviews

WATERFRONT PENTHOUSE OAK BLUFFS

JustynRating, 5 stars8 months ago
We spent our anniversary at Leslie’s place and it was a beautiful! The views and location was like no other and we would book again! Leslie was very responsive and even left us some dinner when we came in late from the ferry. The restaurant staff were friendly and it was everything described in the listing. We didn’t want to leave!
Top guest favorite
A spacious garden area is shown, featuring a large tree providing shade alongside the main residence. Lush green grass extends throughout the yard, complemented by colorful flower beds. A stone border outlines the garden, enhancing the serene outdoor environment.
Apartment in Westport
4.94 out of 5 average rating, 265 reviews

15 Acres of Open Fields & 15 Minutes to the Beach

AnnabelRating, 5 stars3 months ago
Cathleen made our one night stay easy and comfortable. The place was easy to find and nice and warm when we arrived. Streaming services on TV and lots of linens and cooking equipment as promised.
Guest favorite
A spacious living area features two comfortable sofas arranged around a central coffee table. Natural light comes through the windows, while a TV is positioned across from the seating. Air conditioning is present, contributing to a cool and refreshing atmosphere.
Apartment in Wareham
4.92 out of 5 average rating, 157 reviews

☀️ Open & Bright, Ocean Views, Close to Beach!

DevanieRating, 5 stars4 months ago
We loved our stay! Went on off season to go to polar express and was so convenient! Walked with the kids to dinner-then ice cream and breakfast! The beds were comfortable, place was very clean and had such a refreshing get away. Would absolutely stay again
Top guest favorite
A comfortable living area features a gray sofa adorned with decorative pillows, facing a wooden coffee table. A desk in the corner is set for work. A dining area is visible through an archway, showcasing a large table set against neutral walls.
Apartment in New Bedford
4.9 out of 5 average rating, 298 reviews

Walk downtown from our terrace apartment

JenniferRating, 5 stars1 week ago
My husband and I throughly enjoyed our stay! Beautiful quiet home. Restaurant recommendations were very helpful! would recommend this place to anyone looking to visit the area!
Superhost
A cozy living area is presented with a dark couch and a wooden dining table accompanied by black chairs. A TV is situated on a light-colored media unit, while bookshelves filled with books line one wall. Natural light filters in through sheer curtains.
Apartment in Fairhaven
4.77 out of 5 average rating, 105 reviews

Main Street on the Park

ChrisRating, 5 stars3 weeks ago
This was a great spot for us. It was easy to get in and out and explore around. We really enjoyed the use of this apartment, it met all our needs, was clean and tidy and had all we could ask for. We enjoyed getting to explore around the town and were appreciative of the helpful guidebook that was provided in the apartment. She was friendly and helpful and we enjoyed talking with her as we came and went during our time. The neighborhood is a cool area that we enjoyed exploring. This spot helped make our trip a great one.
Guest favorite
The living room features a cozy couch adorned with accent pillows and a blue upholstered chair. A white coffee table sits on a textured rug, while a sliding glass door provides views of the lush greenery outside. Soft natural light illuminates the space.
Apartment in Barnstable
4.95 out of 5 average rating, 120 reviews

Centerville Studio with Town Beach Pass

CarrieRating, 5 stars4 weeks ago
Great home for our superintendent to stay in while working on a project. Highly recommend!
Top guest favorite
A wooden trellis gate is surrounded by lush greenery and low shrubs, providing a natural entrance to a serene garden area. Sunlight filters through the foliage, creating a peaceful and inviting atmosphere.
Apartment in Oak Bluffs
4.98 out of 5 average rating, 202 reviews

Sunny Studio Apartment on Martha's Vineyard

VirginiaRating, 5 stars1 week ago
Paige And Roberto ‘s Airbnb is in a beautiful location. The apartment is absolutely lovely, tastefully decorated and very comfortable. It feels like home. It was such a nice experience for us. Yes we would love to return again one day.
Top guest favorite
A cozy living space is shown with a comfortable couch, a coffee table, and a vibrant table set for dining. Large glass doors provide a view of the outdoors, while a decorative fireplace adds warmth. A washer and dryer are visible in a designated area.
Apartment in Little Compton
4.96 out of 5 average rating, 318 reviews

Home by the Sea

KeithRating, 5 stars7 months ago
I’ve stayed in this home several times. The home is beautiful with a nautical theme throughout. Norm is always friendly, proactive, and responsive. It’s very quiet in a gorgeous New England setting. It’s like a second home when I’m in Little Compton.

Condo rentals with outdoor seating

Guest favorite
A modern living area features a comfortable sofa adorned with cushions, a decorative table, and a vase with flowers. A spacious kitchen is visible in the background, equipped with stainless steel appliances and stylish bar seating for two. Natural light filters through framed windows.
Condo in Nantucket
4.96 out of 5 average rating, 70 reviews

Newly renovated one-bedroom condo in Town

MargueriteRating, 5 stars6 months ago
I have been going to Nantucket for 30+ years. We always stayed in Surfside but you definitely need a car if You are that far out. We decided in town would be better since we weren’t bringing a car and this spot was perfect. We could walk to shops and restaurants so it worked out great. The house was cozy and had everything we needed for our vacation. Super clean and comfortable. The back deck setting is beautiful. Loved being close to Hatches and Cumberland Farms for ice Cream runs. Would definitely book again.
Guest favorite
A modern kitchen is featured, with sleek cabinetry and stainless steel appliances. A large refrigerator and gas stove are visible. Stone countertops provide ample workspace, complemented by a breakfast bar with four blue chairs. Natural light streams through the window, enhancing the open atmosphere.
Condo in Nantucket
4.96 out of 5 average rating, 113 reviews

Updated, modern and charming condo!

JulieRating, 5 stars4 months ago
Great space!! We came for the Christmas Stroll and had wonderful access to restaurants and it was an easy walk or cab ride to town. Inga had the place beautifully decorated for Christmas, even a real Christmas tree! We appreciated all the little touches! The bedding was super comfortable and the backyard space was very cute though we didn’t use it! The quick walking path to Stop and Shop, Island Kitchen, Sea Grille and some other great spots was so convenient but could definitely use a clean up ! Overall, we loved our stay! Thank you!!
Guest favorite
A spacious studio features a queen bed with a decorative throw blanket and a vibrant pillow. A kitchenette with a stove, refrigerator, and sink is visible, alongside shelving and a window draped with light curtains. Blue accents are present throughout the room, creating a fresh ambiance.
Condo in Dennis Port
4.94 out of 5 average rating, 169 reviews

#6 Ocean Oasis Studio, 300 Yards to Glendon Beach

MarciaRating, 5 stars6 months ago
What a darling space! We felt right at home. It was quiet and cute inside and we were able to really relax. Thank you, Sam for such creating an inviting living area!
Superhost
A spacious living area features a comfortable couch and a wooden coffee table. Light wood paneling creates a calming ambiance. A ceiling fan is visible overhead, and doorways lead to other rooms. A small microwave and white lamp are positioned within the space.
Condo in Dennis Port
4.77 out of 5 average rating, 39 reviews

Seaside 2 BR Condo (111-5)

TammyRating, 5 stars9 months ago
Perfect location right near the beach, cosy place to stay with everything we needed to be comfortable. Loved it!
Guest favorite
A clear blue swimming pool is surrounded by lounge chairs positioned for relaxation. Lush greenery provides a natural backdrop, while a shaded area offers protection from the sun. Steps lead from the pool to a nearby structure, adding convenience for guests.
Condo in Tisbury
4.91 out of 5 average rating, 47 reviews

Private 3bdrm Condo Tashmoo Woods

JamikaRating, 5 stars8 months ago
What a relaxing and wonderful stay! Barbara’s place was welcoming and even better than the pictures. The house has everything you need and the addition of the community pool was the cherry on top. The host was extremely responsive and helpful. We look forward to returning to Barbara‘s place the next time my family and I visit MV.
Superhost
A wooden sign is displayed on a light-colored wall, featuring the phrase 'Heaven is a little closer by the Beach' in white lettering on a teal background. The sign is framed in a rustic white border, enhancing its coastal charm.
Condo in West Dennis
4.84 out of 5 average rating, 51 reviews

Hidden Hideaway

JennyRating, 5 stars6 months ago
The location is fabulous and very close to many amenities - coffee, groceries, restaurants and the beach. While it was a small space, it was well laid out, comfortable to be in, very clean and had a respectable kitchen for its small size (which I used). Devon was very proactive and friendly when I asked him about the microwave not working - I had missed that it wasn't plugged in! The condo was very quiet at night even though it is close to a road. I will definitely return to Devon's place should I need to travel there and it is available.
Top guest favorite
A private deck features a glass-topped table set for dining, surrounded by black metal chairs. Soft blue cushions add comfort to the seating area, while a vase with yellow tulips brings a pop of color. The tranquil view of Deans Pond complements the inviting outdoor space.
Condo in New Seabury
4.94 out of 5 average rating, 72 reviews

Summer @ Serenity By The Sea, Mashpee , MA

GeorgeRating, 5 stars7 months ago
Our second visit. We love the place. Quiet but close to great beaches and the Popponesset Marketplace is 2 minutes walk away, with fish restaurants and small stores with necessities (including wine and beer!). A highlight of this visit was sitting on the patio in the morning and 3 times seeing an osprey dive to the pond and catch a fish.
Guest favorite
The exterior of the condo is shown, featuring a well-maintained entrance with a white door and a decorative window. Blue shutters complement the tan shingle siding. A small white table is positioned beside a folding chair on the porch, surrounded by neatly trimmed hedges and grass.
Condo in Dennis Port
4.94 out of 5 average rating, 32 reviews

Dennisport Beach Condo, Unit 5

ShonnaRating, 5 stars8 months ago
We stayed at Stephanie ‘s place last summer and had a blast. We returned this summer to continue our new Cape Cod tradition. Stephanie was very responsive and friendly and we had a great stay. You can’t beat the location with the beach just down the street. The beds were comfortable and we had everything we needed. We will definitely be back again next year!

Quick stats about vacation rentals with outdoor seating in Chilmark

  • Total rentals

    100 properties

  • Nightly prices starting at

    ﺩ.ﺇ441 before taxes and fees

  • Total number of reviews

    2.5K reviews

  • Family-friendly rentals

    80 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

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