Holiday rentals with outdoor seating in Chilmark

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

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Popular amenities for Chilmark outdoor seating rentals

Holiday House Rentals with Outdoor Seating

Guest favourite
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 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 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 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!

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!
Guest favourite
Apartment in East Dennis
4.86 out of 5 average rating, 153 reviews

Peace By The Bay

JohnRating, 5 stars5 months ago
Great apartment. Close to the beach and great restaurants, but also quiet and peaceful. Slept better here than I do at home.
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.
Guest favourite
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 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.

Condo rentals with outdoor seating

Guest favourite
Condo in Dennis Port
4.84 out of 5 average rating, 76 reviews

Comfy Cape Escape! Spacious, Cozy, Close to Beach!

ChrisRating, 5 stars8 months ago
Wonderful beach location. We enjoyed the local walkable beaches and restaurants. Close to anywhere in the cape , we had a great trip.
Guest favourite
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
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 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.
Superhost
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.
Superhost
Condo in East Dennis
4.89 out of 5 average rating, 9 reviews

Bright & Breezy Bayside Condo

KingsleyRating, 5 stars6 months ago
Joanne’s place was spacious and comfortable. There was plenty of closet and drawer space and it would work well for an extended stay. It’s quite near the beaches and harbor in Dennis/Quivet Neck, and there is a good restaurant (Marshside) with a scenic view that is a short walk away. Easy to find, although if you check in at night a flashlight will be very helpful. ;-) The kitchen was small but usable, and the refrigerator was modern and had plenty of room.
Superhost
Condo in West Yarmouth
4.75 out of 5 average rating, 4 reviews

Cape Cod, South Yarmouth July 19-26. Sleeps 8

RickyRating, 5 stars33 months ago
Loved the location and the apartment was facing the water, which meant a light cool breeze most of the time all day and night. The 2 bedroom apt was very clean and spacious and the 5 of us did not get in each of our ways. While inside, we did not hear any noise from our next door neighbors and sliding doors silenced any outdoor noise. The AC was cold and very comfortable. Amenities including additional outdoor access to a peaceful water area with picnic tables, Adirondack chairs was a huge plus. Indoor pool helped too with two little ones. Beach parking passes at a discount. Staff was very nice and accommodating. Parking was easy and plenty of spaces. Would recommend and we would stay again.
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.

Quick stats about holiday rentals with outdoor seating in Chilmark

  • Total rentals

    100 properties

  • Nightly prices starting at

    $188 AUD 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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