
Vacation rentals with outdoor seating in Western Massachusetts
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Top-rated outdoor seating rentals in Western Massachusetts
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Popular amenities for Western Massachusetts outdoor seating rentals
House rentals with outdoor seating

Lake front retreat - Stylish Berkshire home
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!

Historic Williams House
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!

Linny's Lakeview Cottage – Cozy, Fun & Updated !
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
Woodstock Historic Artist Estate - The Pond House
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.

Lake House in the Berkshire (Access Dock & Canoe
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.

Real Estate:Therapy - Lake, Laundry, Love it
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.

19th c. Barn in The Berkshires
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.

Granite Ledge, Modern home in a unique setting
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

Warm & Stylish Apartment w/laundry - walk to DT
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.

Shakespeare’s Folly Side Farm and AirBnB.
William is an excellent host and his place is wonderful. I’ve stayed with him. Multiple times. Recommended!

Relaxing Spa Retreat~Gorgeous View~Walk to Village
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!

King Bed|Wi-Fi|2m Ski Resort
Perfect place to stay while enjoying Great Barrington and the Berkshires.

The Beer Diviner Brewery Apartment
Great place to stay and the owners are super friendly! Highly recommend and we’d love to come back.

River View Apt in Shelburne Falls Historic Village
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

Mountain View Retreat~Sunny Hill Golf / Skiing
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.

Modern Copake Falls Getaway - 8 Mins to Catamount
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

Mount Snow Ski Chalet
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.

Spacious 3 bedroom apt in Lenox historic downtown
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!

Summer Dream! The Handle Lodge at Snowtree Condos
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.

Ideal location! Steps to Track and Broadway!
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)!

Great 2 bedroom condo at Stratton Mountain
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!!

Ski Condo 5 Min from Mt Snow
Lovely home, looked just as described, very responsive/ accommodating host. Stunning Mountain View’s whichever direction you drive. Will definitely be coming back here!

Lovely 1bedrom apartment with screened in porch
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!

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
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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- Six Flags New England
- Albany Center Gallery
- Bushnell Park
- Jiminy Peak Mountain Resort
- Taconic State Park
- Berkshire East Mountain Resort
- Catamount Mountain Ski Resort
- Kent Falls State Park
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- Brimfield State Forest
- Norman Rockwell Museum
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- Mohawk Mountain Ski Area
- Beartown State Forest
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Hartford Golf Club
- Hancock Shaker Village
- Mount Sugarloaf State Reservation
- Naumkeag
- Brignole Vineyards
- Bousquet Mountain Ski Area
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