Vacation rentals with outdoor seating in Chilmark

Find and book unique accommodations with outdoor seating on Airbnb

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Popular amenities for Chilmark outdoor seating rentals

House rentals with outdoor seating

Guest favourite
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 favourite
Home in Fairhaven
4.93 out of 5 average rating, 29 reviews

Lovely Day Oceanside

BethRating, 5 stars1 week 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
Home in Marstons Mills
4.88 out of 5 average rating, 133 reviews

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

JulieRating, 5 stars4 months ago
This was a family Christmas getaway, and it was perfect.
Guest favourite
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 favourite
Home in Westport
4.85 out of 5 average rating, 106 reviews

Beach Home – Family Friendly - Solar Powered

ReneeRating, 5 stars1 month ago
This house was a perfect place for our annual family gathering. There were 9 people from 16 to 83. The open space, first floor bedroom and bunk room were perfect for our group! Ciara was a great host!!
Superhost
Home in New Seabury
4.91 out of 5 average rating, 34 reviews

New Seabury home, private yard, great location

MikeRating, 5 stars6 months ago
Comfortable yet spacious home nestled in the woods of New Seabury. Great location to visit beaches and restaurants. Just minutes from Mashpee Commons and Falmouth for shopping and dining. Beautiful place, Thanks Alex!
Guest favourite
Home in Falmouth
4.89 out of 5 average rating, 55 reviews

Charming 2 Bed Steps to Falmouth Heights Beach

JacqueRating, 5 starstoday
LOVE Billy’s house!! So cute and comfy! We didn’t sleep in the twin beds, but the master bedroom was very comfortable! The doggies loved the bed too!! The patio was great, we used the grill and fireplace! Loved the fenced in yard for the dogs! The neighborhood was very quiet. Billy always responded quickly with any questions. Great restaurants a short drive away and plenty of parking (it’s still off season for the Cape). Billy left a bottle of wine for us from a local winery (Cape Cod Winery). It was good and we went to the winery. Good wine, great outdoor seating (and has covered areas if it’s raining). It’s also dog friendly and they serve food, which was tasty! We went to see Nobska Lighthouse (inside was closed), which was about a 13 minute drive. The views were fabulous! We also went to a small aquarium (only open during the week) in Woods Hole - another short drive. The aquarium was free, but keep in mind, it is small, but nice. Would definitely stay here again!
Top guest favourite
Home in Edgartown
5 out of 5 average rating, 18 reviews

Valentine's Retreat Hot Tub Fire Pit Trails Beach

DaniellaRating, 5 stars1 week ago
Genainna’s place was great! It was very big so my group was comfortable with the beds available, there were many amenities and detailes like extra toothbrushes or other things that I thought were great! It is a beautiful home

Apartment rentals with outdoor seating

Superhost
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 favourite
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.
Top guest favourite
Apartment in Little Compton
4.96 out of 5 average rating, 106 reviews

Coastal Oaks Little Compton

JessicaRating, 5 stars6 months ago
We stayed at Mike&Cora's for the second time and would always come back! Loved it!
Top guest favourite
Apartment in New Bedford
4.9 out of 5 average rating, 299 reviews

Walk downtown from our terrace apartment

DeborahRating, 5 stars1 week ago
This was the nicest airbnb I've stayed in. It feels like a home rather than a commercial rental. I was looking for a writing retreat and this place was perfect. It has two nice workspaces, comfy reading chair and sofa, a kitchen fully stocked with staples.cookware and small appliances, so I could whip up meals easily when I didn't want to go out. It's walkable to all the interesting sights and stores around town; I never used my car for five days. The neighborhood is peaceful, and the interior is warm and charming, just enough nice furnishings and fun art without being cluttered. Best of all, Carlina and Bethany are the most thoughtful, generous and warm hosts you could wish for. They anticipated my every need before and during my stay, responded immediately to questions, supplied me with fresh eggs from their hens, and in general, made themselves completely available while respecting my desire for a solitary retreat. If I lived in New Bedford, I know we'd be good friends.
Superhost
Apartment in Fairhaven
4.77 out of 5 average rating, 105 reviews

Main Street on the Park

ChrisRating, 5 stars1 month 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 favourite
Apartment in Barnstable
4.95 out of 5 average rating, 120 reviews

Centerville Studio with Town Beach Pass

CarrieRating, 5 stars1 month ago
Great home for our superintendent to stay in while working on a project. Highly recommend!
Top guest favourite
Apartment in Oak Bluffs
4.98 out of 5 average rating, 202 reviews

Sunny Studio Apartment on Martha's Vineyard

VirginiaRating, 5 stars2 weeks 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 favourite
Apartment in Edgartown
5 out of 5 average rating, 106 reviews

Stylish retreat | walk to town | fire pit

Kathleen MarieRating, 5 stars3 months ago
Perfect experience Immaculate, well designed. Great light, comfortable bed, great location Could not have been happier on our 2 day anniversary getaway!

Condo rentals with outdoor seating

Guest favourite
Condo in Tisbury
4.98 out of 5 average rating, 50 reviews

Short Walk into Town - Nice Comfortable Reasonable

AshleyRating, 5 stars8 months ago
Walkable to all local shops. Unit was clean and the kitchen was fully stocked with all items needed to prepare and enjoy a meal.
Guest favourite
Condo in Vineyard Haven
5 out of 5 average rating, 21 reviews

Relax....You're on Island Time......

JocelynRating, 5 stars8 months ago
Lovely home and well outfitted for our stay. Conveniently located on well maintained grounds.
Guest favourite
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.
Guest favourite
Condo in Tisbury
4.9 out of 5 average rating, 72 reviews

Sunny 2bedroom condo w pool, walk to town

MicheleRating, 5 stars6 months ago
We were very happy with this comfortable 2 bedroom condo. Very clean and furnished nicely. Easy walk into town for shopping and dining. We had a few questions, which Leah answered quickly and in a friendly manner. Would stay again. Thank you Leah!
Top guest favourite
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.
Superhost
Condo in Hyannis
4.79 out of 5 average rating, 14 reviews

Charming Hyannis 3 Bed 2 Bath

KiaraRating, 5 stars7 months ago
Had to call maintenance for a couple of reasons but responded quickly.
Guest favourite
Condo in New Bedford
4.98 out of 5 average rating, 57 reviews

Millie's-Historic New Bedford, 2BR, water views

KeithRating, 5 stars2 months ago
Condo is beautiful as is The view and location. Jennifer was quick to respond and a great host. Neighborhood is filled with great restaurants. Definitely going to stay there again in the future...
Guest favourite
Condo in Hyannis Port
4.85 out of 5 average rating, 82 reviews

Short walk to the Beach and Downtown Hyannis!

TroyRating, 5 stars3 months ago
Billy is an outstanding host. He was notably responsive to any questions no matter how insignificant and was very helpful. The location is super convenient to restaurants and attractions. Neighborhood is quiet and good area to relax. I highly recommend this host if you find yourself headed to the area. Great time!!

Quick stats about vacation rentals with outdoor seating in Chilmark

  • Total rentals

    100 properties

  • Nightly prices starting at

    $166 CAD 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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