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Holiday rentals with outdoor seating in The Berkshires

Find and book unique Holiday Houses with Outdoor Seating on Airbnb

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Popular amenities for The Berkshires outdoor seating rentals

Holiday House Rentals with Outdoor Seating

Top Guest favourite
Home in Spring Glen
4.98 out of 5 average rating, 186 reviews

Creekside cottage on 65 acres of land

SavaRating, 5 stars2 weeks ago
The place was super serene and peaceful—perfect for a relaxing getaway. The house was incredibly well maintained, clean, and cozy. Highly recommend to anyone looking for a comfortable and quiet retreat
Guest favourite
Home in Germantown
4.97 out of 5 average rating, 336 reviews

Fantasy Cottage/Mountain Views/Trails/Fire pit

DenzeylRating, 5 stars2 weeks ago
Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.
Guest favourite
Home in Woodstock
4.94 out of 5 average rating, 338 reviews

Woodstock Historic Artist Estate - The Pond House

CodyRating, 5 stars1 month ago
No notes, incredible escape even in the pouring rain. The ambience, even down to the little things like walking through the door to classical music, was truly top notch.
Guest favourite
Home in Copake
4.96 out of 5 average rating, 195 reviews

Lakefront +pets +skiing +bbq +firepit +games

RichRating, 5 stars2 weeks ago
We had a great time, the location is great, right on the water and the fishing was even better. A very quiet lake and much bigger when you are out on it in the kayaks. I would surely stay here again!
Guest favourite
Home in Ghent
4.88 out of 5 average rating, 318 reviews

Modern Barn on 12 acres w Sauna, FirePit+swimming

JasonRating, 5 stars3 weeks ago
Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.
Top Guest favourite
Home in Lexington
4.99 out of 5 average rating, 113 reviews

Mountain View Chalet: AC, Hot Tub, Firepit, Games

AlexaRating, 5 stars2 weeks ago
What an excellent stay - this airbnb was incredibly well stocked with kitchen supplies, games, extra linens, really anything that one could want. Amenities were high quality and very thoughtful.
Guest favourite
Home in Kerhonkson
5 out of 5 average rating, 271 reviews

Cook House | Modern Cottage w/ Hot Tub & Fireplace

MartimRating, 5 stars1 month ago
Beautiful place, we loved the hot tub, the fire pit the gorgeous bedroom and fully stocked kitchen. A dream to cook and hang out in. This is a place you want to stay in and not leave. Internet and wifi was excellent. Communication was great. The projector system didn't work at all and we did get some help, and when they weren't able to help they offered us a free night stay if we wanted to stay another day. However, please stop with the AI responses they are not helpful and just make it feel less responsive once you realize it's not a human. Cons were just that the sofa isn't very comfy or loungeable, but that's really it. Thanks for a lovely stay!
Guest favourite
Home in Hunter
4.95 out of 5 average rating, 147 reviews

Modern House with Mountain View @Getawind

SamRating, 5 stars3 days ago
Loved the place. Beautiful setting and the house was well stocked with everything we needed. Highly recommend for an escape from civilization.

Apartment rentals with outdoor seating

Guest favourite
Apartment in Plainfield
4.97 out of 5 average rating, 271 reviews

Sunny, light filled loft in 1873 Colonial

DouglasRating, 5 stars2 weeks ago
Peter and the apartment were great! Peter was super responsive, friendly, and had nice touches like homemade granola with milk and coffee provided. After my original AirBNB fell through at check-in at 6pm, I was relieved (and saved) by Peter’s responsiveness.
Top Guest favourite
Apartment in Canaan
4.99 out of 5 average rating, 144 reviews

West Main

AlexisRating, 5 stars2 weeks ago
Loved this little apartment. It has everything you need and more.
Top Guest favourite
Apartment in New Paltz
4.97 out of 5 average rating, 544 reviews

Relaxing Spa Retreat~Gorgeous View~Walk to Village

LacieRating, 5 stars4 weeks ago
Ami’s place was great! Stayed for my birthday and was surprised with a delicious tres leche cake upon my arrival! The view was incredible, amenities were amazing, overall it was everything I hoped for and more. Thanks Ami!
Superhost
Apartment in Philmont
4.9 out of 5 average rating, 118 reviews

Beautiful space in the heart of Philmont

JessicaRating, 5 stars8 months ago
Wonderful stay! Beautiful home and so much to do in the area. We had a great time!
Top Guest favourite
Apartment in Petersburgh
4.88 out of 5 average rating, 185 reviews

The Beer Diviner Brewery Apartment

JohnRating, 5 stars1 week ago
Cute room above the brewery was a nice get away for my wife, our little dog, and I. John was friendly and so were all of the other employees and guests. The Irish band was great and the patio by the brewery was very cozy the beers were also delicious too. The room itself was spacious and well furnished with a good size bed and additional day bed. Fun weekend get away for all ages.
Top Guest favourite
Apartment in Plainfield
4.95 out of 5 average rating, 271 reviews

Sunny carriage house apartment

EllieRating, 5 stars2 weeks ago
We had a great time at this lovely spot! Erin was a very kind and responsive host, and the apartment was just as described :)
Top Guest favourite
Apartment in Coxsackie
5 out of 5 average rating, 115 reviews

Hudson River Beach House

HeidiRating, 5 stars2 days ago
Love Janet, love her property, love the atmosphere……….PERFECT in every way! Any need……Janet was doll! Will be back!
Guest favourite
Apartment in Winchester
4.91 out of 5 average rating, 380 reviews

Gateway to the Berkshires

ThayerRating, 5 stars2 weeks ago
The place was beautifully decorated and everything from the plants to the antiques was wonderful to see. This is the perfect place for any stay and they only ask that you respect the possessions. John was very responsive in helping us for a late check in.

Condo rentals with outdoor seating

Top Guest favourite
Condo in Dover
4.99 out of 5 average rating, 120 reviews

Summer Dream! The Handle Lodge at Snowtree Condos

MarkRating, 5 stars3 months ago
Our family enjoyed our stay at Rafael's condo. The space was very clean and comfy, and exactly matched the description and photos posted here. The fireplace was a great draw, too. If you're planning on skiing at Mt. Snow, the Moover shuttle bus stop is located right outside of this building, which made for a very convenient and quick way to get to Mt. Snow for my family of 4. We would certainly stay here again in the future.
Top Guest favourite
Condo in Norwich
4.98 out of 5 average rating, 108 reviews

CASiNO, Spa, Hot Tub, Pool, King bed, sauna

MelindaRating, 5 stars1 week ago
The Villa was exactly as described! Easy communication with owner. A perfect getaway weekend, every amenity we could want or need! Look forward to visiting again in the near future!
Guest favourite
Condo in Vernon Township
4.95 out of 5 average rating, 191 reviews

Comfy Studio at Mountain Creek Resort

LaurieRating, 5 stars6 days ago
This is a beautiful place. Second time we’ve stayed there and I would like to come again next year!
Top Guest favourite
Condo in Norwich
4.98 out of 5 average rating, 183 reviews

Peaceful Oasis steps from Mohegan Sun

RaeneshaRating, 5 starstoday
Christina’s place is exactly as described and what you see in a photo. It is very clean and feels like you’re right at home. The place is clean and will book again. Thank you again.
Top Guest favourite
Condo in Vernon Township
4.95 out of 5 average rating, 147 reviews

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna

TeraRating, 5 stars1 month ago
Kurk's place is updated nicely. Bed is comfy. The tub is amazing! The resort is very nice, the scenery and mountains surrounding it are beautiful, and the condo all made for a relaxing stay!
Top Guest favourite
Condo in Dover
4.92 out of 5 average rating, 123 reviews

3 Story Condo - 5 Minutes to Mount Snow!

AlyssaRating, 5 stars2 weeks ago
It was such an easy check in and check out process. He let us check in an hour early since we arrived earlier. Place is spacious and exactly as described. Highly recommend!
Guest favourite
Condo in East Jewett
4.97 out of 5 average rating, 125 reviews

MountainViewBrightCondo10MinToColgateLakePool

KennaRating, 5 stars4 days ago
Wonderful stay!! Very clean and cozy space. The host was easy and lovely to communicate with!
Top Guest favourite
Condo in Lanesville
4.98 out of 5 average rating, 570 reviews

Trendy Condo Hunter Mountain

TyreseRating, 5 stars2 weeks ago
Absolutely great place to unwind without missing out on comfort our host was VERY nice and proactive she ensured we had all the information we need and the place was clean and very comfortable definitely recommend.

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