Vacation rentals with outdoor seating in Western Massachusetts

Find and book unique outdoor seating rentals on Airbnb

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Popular amenities for Western Massachusetts outdoor seating rentals

House rentals with outdoor seating

Guest favorite
Home in Becket
4.94 out of 5 average rating, 150 reviews

Lake front retreat - Stylish Berkshire home

ShaiRating, 5 stars2 weeks ago
We had a wonderful time at this beautiful lake house! The home itself is lovely—spacious, comfortable, and perfect for a family getaway. The lake and boats were a big highlight for us, offering plenty of fun and relaxation. Our host was incredibly responsive and helpful throughout our stay. While there were a few small things that needed fixing, she addressed them right away and was very communicative, which we really appreciated. Overall, it was a great experience and a memorable holiday for our family. We’d definitely love to come back!
Guest favorite
Home in Northampton
4.94 out of 5 average rating, 189 reviews

Historic Williams House

DorothyRating, 5 stars3 weeks ago
I stayed at Kaitlyn’s magical home with two friends during our Smith College reunion weekend. The house is historic, charming, cozy, and comfortable. The beds are comfortable and we rested well. The sounds of birds chirping and the many thoughtful details throughout the house made us feel welcome and at home. I hope to return!
Top guest favorite
Home in Southwick
4.96 out of 5 average rating, 218 reviews

Linny's Lakeview Cottage – Cozy, Fun & Updated !

SarahRating, 5 stars4 weeks ago
We had an amazing time at Linny’s! Space was cozy, clean, and included all the right things to make our stay comfortable and easy for the long weekend! Thanks so much for sharing your home with us! Warmly, Sarah SC
Guest favorite
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.
Superhost
Home in New Marlborough
4.88 out of 5 average rating, 134 reviews

Lake House in the Berkshire (Access Dock & Canoe

ShwuRating, 5 stars4 months ago
We enjoyed our stay at the house. Mitchell was very responsive and communication was easy. The house is near butternut and GB. Hopefully we will come back in the summer to enjoy the outdoors.
Guest favorite
Home in Becket
4.88 out of 5 average rating, 346 reviews

Real Estate:Therapy - Lake, Laundry, Love it

ElizabethRating, 5 stars1 day ago
Lovely house with all the necessities. Beds were comfortable, kitchen had all the necessary items and bathroom was clean. It was a perfect retreat and we enjoyed sitting outside around the fire pit.
Superhost
Home in Cheshire
4.85 out of 5 average rating, 214 reviews

19th c. Barn in The Berkshires

JohnRating, 5 stars6 months ago
Our party of four adults and two small kids really enjoyed our weekend in this unique and tastefully renovated former barn. The linens, bedding, and towels were all top quality, the kitchen was well equipped, and overall the place was comfortable and spotless. The location is super private and quiet, surrounded by nature and farmland, including an on-site stream and sheep (that's not a typo). A great spot to stay for a visit to the northern Berkshires - Mt. Greylock and Mass MoCA are very nearby. Our visit was on a frigid winter weekend with a ton of snow and outside temps in the 20s, yet our indoor temps were toasty and very comfortable, especially with the wood stove.
Top guest favorite
Home in Great Barrington
4.99 out of 5 average rating, 122 reviews

Granite Ledge, Modern home in a unique setting

MichaelRating, 5 stars2 weeks ago
Had a wonderful time at Granite ledge. Absolutely beautiful backyard. Very peaceful and comfortable. The bed was very comfortable and we slept like babies. Highly recommend and would definitely stay here again.

Apartment rentals with outdoor seating

Guest favorite
Apartment in Northampton
4.93 out of 5 average rating, 107 reviews

Warm & Stylish Apartment w/laundry - walk to DT

KelliRating, 5 stars3 months ago
Heather's place is amazing...very spacious and was great for my two week stay for work. It really great it is so close to the highway and also local restaurants and shopping. Will definitely stay again if I am in the area.
Guest favorite
Apartment in Marlboro Township
4.93 out of 5 average rating, 265 reviews

Shakespeare’s Folly Side Farm and AirBnB.

DanRating, 5 stars3 weeks ago
William is an excellent host and his place is wonderful. I’ve stayed with him. Multiple times. Recommended!
Top guest favorite
Apartment in New Paltz
4.97 out of 5 average rating, 545 reviews

Relaxing Spa Retreat~Gorgeous View~Walk to Village

StephenRating, 5 stars2 weeks ago
Such a perfect location for a weekend in new paltz and the views from the patio/hot tub are absolutely spectacular. Ami was a great host!
Guest favorite
Apartment in Great Barrington
4.9 out of 5 average rating, 133 reviews

King Bed|Wi-Fi|2m Ski Resort

EricRating, 5 stars6 days ago
Perfect place to stay while enjoying Great Barrington and the Berkshires.
Top guest favorite
Apartment in Petersburgh
4.88 out of 5 average rating, 186 reviews

The Beer Diviner Brewery Apartment

MargaretRating, 5 stars1 day ago
Great place to stay and the owners are super friendly! Highly recommend and we’d love to come back.
Guest favorite
Apartment in Shelburne Falls
4.97 out of 5 average rating, 122 reviews

River View Apt in Shelburne Falls Historic Village

JuliaRating, 5 stars1 month ago
shelburne Falls is an adorable town, and this Airbnb has a small table with 3 chairs on a back porch that looks out on the river and bridge— very nice . Cute apartment over the the owner’s store and perfect location to walk around town . crystal was a great host…. proactive before our arrival responsive
Top guest favorite
Apartment in Freehold
5 out of 5 average rating, 305 reviews

Mountain View Retreat~Sunny Hill Golf / Skiing

TonyRating, 5 stars2 weeks ago
This is a great home. The decor is inviting, the kitchen is spacious, and the backyard has a great view. Really enjoyed the peace and quiet too.
Guest favorite
Apartment in Copake Falls
4.9 out of 5 average rating, 334 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

EunjooRating, 5 stars2 weeks ago
The Airbnb is on a small hill looking out towards a small pond and an open field. The sunset in particular was very nice. The home is in a very private location. Inside, the space was well decorated - simple yet tasteful. The space itself is on the smaller end but the decor opens up the space. Michael answered all questions within 24-hours. Easy to communicate with. Overall a good stay

Condo rentals with outdoor seating

Guest favorite
Condo in Dover
4.83 out of 5 average rating, 108 reviews

Mount Snow Ski Chalet

BarryRating, 5 stars3 months ago
Great place to stay. There are no Ubers the week we stayed there and we should have rented a car. But the place was great.
Guest favorite
Condo in Lenox
4.97 out of 5 average rating, 35 reviews

Spacious 3 bedroom apt in Lenox historic downtown

JamieRating, 5 stars4 weeks ago
Yulia's place was the perfect spot for a Memorial Day weekend getaway. Was even great for an infant! It was comfy and cozy! Loved the patisserie downstairs and the town. Highly recommend!
Top guest favorite
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 favorite
Condo in Saratoga Springs
4.98 out of 5 average rating, 125 reviews

Ideal location! Steps to Track and Broadway!

BrianRating, 5 stars4 months ago
Carla was a wonderful host. More importantly her rental was beautiful and very comfortable. Would strongly recommend and we look forward to going back (when there’s less snow)!
Guest favorite
Condo in Stratton
4.94 out of 5 average rating, 103 reviews

Great 2 bedroom condo at Stratton Mountain

KatieRating, 5 stars3 months ago
Great place to stay conveniently located by the mountain base! We enjoyed walking into the village after skiing. Very clean and cozy and had everything we needed and more. Dana was very responsive! Hope to come again next year!!
Guest favorite
Condo in Dover
4.9 out of 5 average rating, 52 reviews

Ski Condo 5 Min from Mt Snow

JadeRating, 5 stars1 month ago
Lovely home, looked just as described, very responsive/ accommodating host. Stunning Mountain View’s whichever direction you drive. Will definitely be coming back here!
Top guest favorite
Condo in Northampton
4.97 out of 5 average rating, 63 reviews

Lovely 1bedrom apartment with screened in porch

LauraRating, 5 stars1 month ago
Beautiful and very clean space! We had the most wonderful long weekend at Goran's apartment. He was so responsive and super friendly... cannot recommend enough. We will be back!
Superhost
Condo in Dover
4.8 out of 5 average rating, 110 reviews

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

BrendanRating, 5 stars3 months ago
Perfect location to mt snow.. right across the street. It's an older complex but had everything we needed for a few days of skiing.. would rent again

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