House vacation rentals in The Berkshires

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

Very enjoyable time here! Instructions, accommodations, and overall experience was perfect!

It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

Cozy home, on a beautiful property. The natural pool is really special, and we loved staying here. Hope to be back.

The house is really gorgeous. Everything was very new/modern, clean, and comfortable. We enjoyed cooking meals in the kitchen overlooking the stunning view out the back. The hot tub and fire put were nice amenities to enjoy. The BBQ seemed to not be working, but other than that, no complaints. Location wise, the property is located in the northwest Catskills, near Stamford, NY, and convenient to many hiking spots in the area as well as nearby towns. The property itself its up on a hill, in what felt like a secluded and private spot, which made it feel like a real getaway and retreat. In sum, recommend this Airbnb for the nice amenities, modern touches, and amazing view.

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

This was my first ever experience with AirBNB. I couldn't have stayed at a better location for my first experience! Melissa's home was warm welcoming and beautiful. I stayed for four nights with my four children. There was plenty of space for all of us. Although my youngest still chose to sleep with me lol the bed was still big enough for the two of us. The pool was absolutely perfect, my kids loved it! The hot tub was very relaxing and very easy to use. My kids really enjoyed it too. The grill worked wonderfully and the fire pit was great for smores. The covered patio made watching my kids enjoy the pool even more relaxing for me, I'm a ginger so if I can be outside and out of direct sunlight that's a huge bonus for me. The kitchen had everything we needed as well. Melissa was very responsive when I had questions and I cannot thank her enough for the great week. We'll be back next June for another week! Can't wait to return to this fantastic vacation spot!

We really enjoyed our time at Elizabeth Jane's place. The home is spacious and quaint, with nice furnishings, a tasteful colonial feel and easy access to downtown Litchfield and the Berkshires. The bucolic setting is lovely - scenic, relaxing and peaceful.

We had a wonderful time and this house is completely amazing. There is absolutely nothing missing! When Tiffany said, "all you need to bring are clothes" she wasn't joking. The person who designed the house was a genius with the master bedroom on one side of the house, the 2nd bedroom on the other side and the 3rd on the 2nd floor. Privacy inside as well as outside. It was a hiking trip for the family and included Kennedy Park, Olivia Outlook and the Great Monument Mountain. After spending the day hiking, the hot tub, playing pool and watching a movie in the theater just ended a perfect day. We didn't realize how close we were to MA and it was bonus to explore Western Mass as well. Thank you Tiffany for sharing your home with us.

Loved every part of our stay with Kristine. Perfect for a romantic weekend away - gorgeous cabin, well appointed, and great kitchen for cooking-in. Her recommendations for local spots were also so thoughtful. Thank you again!

We had a wonderful stay at James and Lissy’s house! It was perfectly located for getting around the Berkshires. The house was clean, beautiful, and cozy. When we needed to communicate with James and Lissy they were incredibly responsive and helpful. Every year, my friends from high school and I meet up for a reunion in the Berkshires (we have been doing this annually), and the hope is to stay in this very Airbnb next year, if possible/ available! It was an exceptional Airbnb experience!

We stayed at Caroline and Nathaniel’s beautiful home over the winter and celebrated NYE’s. Their house is beautiful and perched on top of the hills overlooking a lake. The view is absolutely stunning in the mornings. The house was well maintained and clean. The hosts were very active in communicating with us where we needed anything or if we needed to be aware of any situations regarding the house. I would definitely stay here again.

Perfect location for a few friends that came for a birthday party. Was perfect. I didn’t worry about them at all, and I knew they had a quality stay

We stayed here on our way to Stowe to break up our long drive with an 8 and 2 year old. It ended up being a wonderful mini trip that we didn't want to leave. The house exceeded our expectations in terms of quality, cleanliness, and amenities. And the location was excellent - about 10 to 12 min to the nearest grocery store and downtown with restaurants, Edith Wharton's estate about 20 min away, and Great Barrington/Stockbridge were easily accessible for day trips. We plan to come back for skiing, and to take advantage of the lake activities in the summer. The only downside was the busy road, as mentioned in the listing, but the traffic quieted down in the evening and it didn't affect our sleep at night with the bedrooms located in the back of the house (husband is a very light sleeper; we did bring and use sound machines just in case).

I was planning on my proposal and wanted somewhere special. The window house was exactly that. Private, peaceful, super clean, amazing views and wildlife. Taylor and Marla were EXTREMELY good at communicating and getting back in a timely manner. If you and your significant other are looking to get away, this is the place. It’s sublime.

The property was as described, beautifully situated by the water in a beautiful location. Lee, the host, provided prompt and responsive communication. the unique outdoor shower and toilet (incinerator toilet) were acceptable for us, but the space was somewhat limited for two adults and two children; it may be better suited for two guests.

Great stay! This is our second time staying at Bradley’s place and it was exactly the same as last time, in a good way. Place was clean, great neighborhood, very quiet!

this place is magical. my sisters and I have stayed here twice now, for her wedding and now for mine. both times the home has been clean and the overall experience has been wonderful.

A beautiful, comfortable house right on the Hudson with stunning views. We loved watching all the life on the river, herons and loons and ducks, as well as boats from tiny crafts to massive barges. There are great hikes just a short distance away. It is a perfect place to rest, write, draw, and make music.

Kellen and Samantha's home and property are very special--a wonderful location for a restful retreat in nature that is also a short drive to several charming towns in northwest Connecticut. The hilltop site offers breathtaking views of surrounding mountains, valleys, and forest. The residence sits atop a long driveway off a gravel road so is serenely quiet and private. Inside, the space was immaculate, thoughtfully designed, and very comfortably furnished. The shower, bed, towels, and linens were all particularly fantastic, as was the full kitchen which allowed us to cook nightly. The area is exceptional for hiking, culinary delights, and all sorts of shops. And our hosts were proactive, helpful, and clear in all of their communications. We really loved staying here, as did our dog, and we hope to return. Highly recommended!

This was hands-down, my favorite. Air B&B ever! We hope to return and spend more time on our next visit. We were literally immersed in and surrounded by nature and it was so beautiful and peaceful. It also felt like home the minute we stepped in… like going to a friend’s “country weekend” place where the books, puzzles, games, records, artwork, handcrafted pottery, electric blankets, dog beds and more (!) just make you feel at ease and in comfort. This place is so loved and it shares that love with its visitors. Thank you to the owners for sharing such a special place!

A truly amazing experience. I wholeheartedly recommend staying at Amanda & John’s home. You won’t find a better, more cared for, more beautifully appointed home. Everything you could ask for and more. Super kind, responsive hosts and every detail is considered. Great WiFi, too. If you’re looking for an experience in a spacious landscape, in quietude, with stars up above, this is the place.

Always a relaxing stay at the farm! We enjoyed the amenities at The Wellness Hut and peaceful walk around the farm. Also, loved that we were able to bring our spoiled puppy.

This place is gorgeous. Angus did an exceptional job decorating and outfitting the home with everything you need (example: perfectly placed phone chargers). We may stay there again if he'll let us. :)