
Vacation rentals with outdoor seating in Chilmark
Find and book unique outdoor seating rentals on Airbnb
Top-rated outdoor seating rentals in Chilmark
Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Chilmark outdoor seating rentals
House rentals with outdoor seating

Cozy Beach Cottage By The Sea
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!

Riverhouse
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.

FREE FERRY Car RESV July WK Game room Central AC
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!

Lovely Day Oceanside
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.

The Mills Retreat- 3BR/2Bath - Beach pass included
This was a family Christmas getaway, and it was perfect.

Haven on the hill
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.

Quaint Cape Beach House
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!

Beach Home – Family Friendly - Solar Powered
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

WATERFRONT PENTHOUSE OAK BLUFFS
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!

15 Acres of Open Fields & 15 Minutes to the Beach
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.

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

Walk downtown from our terrace apartment
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!

Main Street on the Park
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.

Centerville Studio with Town Beach Pass
Great home for our superintendent to stay in while working on a project. Highly recommend!

Sunny Studio Apartment on Martha's Vineyard
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.

Home by the Sea
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

Newly renovated one-bedroom condo in Town
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.

Updated, modern and charming condo!
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!!

#6 Ocean Oasis Studio, 300 Yards to Glendon Beach
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!

Seaside 2 BR Condo (111-5)
Perfect location right near the beach, cosy place to stay with everything we needed to be comfortable. Loved it!

Private 3bdrm Condo Tashmoo Woods
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.

Hidden Hideaway
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.

Summer @ Serenity By The Sea, Mashpee , MA
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.

Dennisport Beach Condo, Unit 5
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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- Brown University
- Sandwich Glass Museum
- Owen Park Beach
- Sagamore Beach
- New Silver Beach
- Onset Beach
- Lighthouse Beach
- Blue Shutters Beach
- Roger Williams Park Zoo
- Oakland Beach
- Grey's Beach
- Scusset Beach
- Pinehills Golf Club
- Nickerson State Park
- South Shore Beach
- Earle Road Beach
- Chapin Memorial Beach
- Agawam Hunt
- Oyster Harbors Beach
- Englewood Beach
- Springhill Beach
- Surfside Beach
- Pilgrim Beach
- Forest Beach