Vacation rentals with outdoor seating in The Berkshires

We stayed for a few days at the zen cottage and it was the most relaxing and peaceful weekend. The cottage is exactly has described and super clean. Alma and James were very helpful and welcoming. Overall had an extremely enjoyable weekend and hope to come back soon

Martina’s cottage was fantastic. Everything was as advertised. Fantastic lighting, large space and, unbelievable views.

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.

We had a wonderfully relaxing stay at Frank’s beautiful home! The house was spotless, well-equipped, and had everything we could have needed for a comfortable visit. We especially enjoyed the easy access to the lake and the close proximity to great hiking trails. It was the perfect spot to unwind and connect with nature. We would love to come back again soon!

We loved our stay at this stunning home! The hot tub and sauna and the views were major highlights for our 10 year anniversary trip! Great for a weekend away!

Well equipped, clean, functional space. Back porch and patio is fantastic for expanding the space and ease of entertainment. Caught some pretty good catfish and carp right off the back stairs/landing. Convenient to many amenities with easy access from rt159 and rt57.

Edina and Glen's house was beautiful, spacious, and pristine. It was the perfect setting for a "girls weekend". The grounds were stunning, and made for a great setting. Very close to town, shopping, and wonderful restaurants. We really appreciated that our hosts were very proactive in reaching out and making all instructions clear. They were communicative and flexible. Thank you for having us in your beautiful home! Very memorable weekend.

We enjoyed the perfect escape from the city in this magical barn with gorgeous antiques and pristine views. Definitely will be back for future celebrations!

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.

Wonderful stay! Beautiful home and so much to do in the area. We had a great time!

We thoroughly enjoyed our stay at the Bennett’s Abode! Larry and Lana’s airbnb had just about everything a visitor would need and they even included a detailed binder full of information and ideas pertaining to the area. Larry was so prompt with his responses and always kept us in the loop. He even provided several great hiking ideas that we utilized throughout our stay at his home. We were so grateful for the overall experience and left with incredible memories!

My new go-to place in the berkshires! I love the berkshires for hiking , my favorite spa (mend), and all the cute shops/food outings! This spot was perfect - it's well-decorated, the bathroom is nice, and the location is GREAT! Loved the back patio for morning coffee. Washer/dryer was fast. Host is very responsive and helpful. Looking forward to my next stay & would love to bring my dog next time :)

Cindy was great with communications, and gave me all of the instructions I needed to make it a pleasant stay for me, my dog, and the hosts. I stayed Friday and Saturday nights, and enjoyed the craft beer and locally made sourdough pizza in the evenings with a talented musical duo playing on Saturday night. The taproom closes at 8pm, and after closing time the apartment is very quiet and peaceful. The apartment is cozy with attractive furnishings and a comfortable bed, but it is not a place for people with mobility challenges. There are 17 steps up to the apartment, and the shower in a free-standing claw-foot tub doesn't have handrails. I enjoyed my stay, and give it a 5-star review for physically fit singles or a couple!

It’s been a little over a week since we stayed here and I cannot stop thinking about it. The pictures in this listing are beautiful but the space is even more incredible in person. I also spent a lot of time sitting on the deck and taking in the view of the mountains - so peaceful! The attention to detail here is unmatched. From check in to checkout, everything is very clear. Communication was great. The guidebook is thorough. And, again, the space really is so well done. You can enjoy the beautiful surroundings even indoors. Highly recommend!

We had a good time. This was a great place with beautiful views!

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.

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!

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.

This is a wonderful property that is close to everything we like to do! Krista is a wonderful host and I’m always excited if her place is available.

We had a great time and the property was immaculate! The hosts came by with extra towels quickly upon request and it was a holiday. Recommended!

We booked the place for a family stay near Woodstock. It was easy to get in. There’s automated messages for every step of the stay with instructions which was very nice and helpful. We had a great stay in a worm and clean space. Would definitely go back.

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.

such a good price for being about 4 minutes away from mohegan sun and around 20 minutes away from foxwoods. texted me with very clear instructions and didn’t have a problem the whole time, would happily stay here again :).

Ali was a great host and extremely responsive! Ali's place was clean and matched the description. It was in the perfect location and very centralized to what we wanted to do. When I visit the Catskills again, I will be booking with Ali!