Guest house holiday rentals in The Berkshires

Gorgeous place in a beautiful town. About a thirty minute walk (or 4 minute drive!) right into downtown with cute shops and restaurants. The cottage is beautiful, clean and so cozy. Highly recommend.

Judy could Jay have been a better host. My children and I were in town for a family function and couldn’t be happier with the stay.

I just want to say that this is a very beautiful place. Julian & Karen were extremely nice to us and to have us there. Karen made sure we were comfortable with the stay, and was very respectful and the place was very cozy and inviting. The place is beautiful and warm. Her recommendations were very helpful and we truly enjoyed ourselves! I will come back again! Thank you so much for your wonderful hospitality!

This bungalow was a magical place to spend an autumn weekend visiting family and the beautiful Hudson valley area. We enjoyed morning walks around the pond with our pup and our coffee. Wish we had time to use the fire pit! Hammocks and bed was comfy, shower and kitchen were clean and lovely! Thanks so much a for a great stay! Would certainly recommend!

We enjoyed our stay at the Carriage House very much. Jennifer is a great host - very attentive with excellent communication.

Great and very cute place, perfect location for skiing

great stay! peaceful location! fun games and painting supplies available. the bed was not too comfy as it is very hard and springy, but made do for one night!

We thoroughly enjoyed our stay at this Airbnb in Woodstock. Joni was very attentive and gave recommendations when asked. Her home was very welcoming and had plenty of amenities. All dining experiences are within walking distance which was a huge plus. Walking trails are all within a reasonable driving distance. It truly was a beautiful experience all around and we hope to be back again soon.

Beth was very kind and responsive. Great place to stay!

This place was a perfect weekend get away for myself and husband. Plenty of space for the two of us. The place was nicely, decorated and fully furnished with accessories if you wish to cook. I enjoyed the spaces between the outside patio as well as the hot tub. Bill was great with giving suggestions of local places, even though I was a local myself.. if you’re looking for a quiet getaway this is your place.

We had an amazing stay at Kristin and Dave’s cottage and cannot wait to return. The cottage was spotless, very well equipped, and supremely comfortable. Both Kristin and Dave were very responsive, extremely helpful, and provided great instructions and assistance. The location was beautiful and so peaceful. The outdoor space was such a nice option, and the porch and pool were so nice to relax in. We wholeheartedly recommend the cottage!

Denise’s place was an amazing gateway from the craziness of the city. If somebody wants to escape and feel the quiet of the nature please book this right away. My boyfriend and me enjoyed this place a lot for the only two days we stay. Thanks Denise’s ❤️✨

John's place is in a great location. Walking distance to downtown Saratoga. Very close to the track. A couple of good Restaurant's near by. Pictures and description of property were perfect. Place was spacious and very clean. Perfect for a couple or 2 couples. We would definitely stay there again.

The cottage is beautiful and such a surprise when you open the front door - the magical stream is right out the window. Although the cottage is close to the road you would never know it - the back patio is just perfect!! An easy drive to a a number of small and lovely quintessentially New England villages. We would highly recommend Jeff and Elizabeth's cottage!

We wanted a quiet weekend, and we got a whole lot more. Andrew and Mynor were amazing hosts!! From the complimentary beverages to the assistance with snow removal, their service was incredible. The photos did not do justice to the place; the decor was great, and the place was spotless. We will definitely be back!!

One of the best Airbnbs we've stayed at. We loved the interior design and how cozy the space was. The location is beautiful and peaceful. Highly recommend.

Jonathan's place is great. It is historic while having all the modern convenience. Jonathan was a great communicator prior to arrival and with local recommendations once we were there. We had a great experience.

This was the perfect place for us to stay for Thanksgiving in Accord with family. Although attached to Jolle's house, it was entirely private with its own entrance and parking area. The cottage is pristine, very nicely put together and so very comfortable. Underfloor heating made it even cosier on a very wintery snowy Thanksgiving Day! Jolle's very welcoming gift of local chocolates, a bottle of wine and coffee in the freezer made us feel welcome. All the local recommendations were helpful and we all decided that this was the place to come back to next time we return to Accord! Highly recommended.

We were in town for a family wedding and this was the perfect place for 20 or so of us to spend the weekend. Everything was great. We were so comfortable and had so much fun! Thank you to Meiling, Martin, Mayra, and all the folks who assist them with housekeeping and logistics. Hope to find an excuse to return, as everyone was sorry when our stay came to an end. Highly recommend without hesitation.

This is a beautiful place and exactly what my wife and I needed for a long weekend away! The barn is so cozy and we felt right at home . The hot tub was a nice treat on the cool evenings and the beautiful view. But by far the best part was the animals living below us that we could give snacks to throughout the day and see through the living space windows. Would definitely recommend this to anyone that loves horses and donkeys!

Upon entry, my architect husband said "Cute Cottage; Susan you did it again." Plenty of room for a couple in their mid-seventies, and a Millennial daughter. The cottage is very well insulated such that I didn't have to run the heat except for fifteen minutes at bedtime in mid-October, yet there is a big south-facing sliding door in each of the rooms where the sun and moon shines through. Beautiful woodland falls away from the cottage and small patio beyond the sliding doors, and moonlight is magic on all the leaves. If we had more time we would have investigated the many books in the shelving. We will find excuses for coming back to the area and will stay here again.

We loved the cottage. If anything it was even cuter in person than in the pictures. Communication was perfect and the place was very well thought out. We enjoyed our stay, I’d recommend it and come back here in the future!

I had a very peaceful stay. The area was quiet and as a light sleeper, I appreciated that. The decor was attractive and I loved the subway tile, sunken kitchen sink, and beautiful counter top. Everything worked fine and the hosts were easy to reach. There’s a nice organic market about three minutes walk away with good prices; it was so convenient to pick up a few groceries. I also appreciated the parking spot right in front of entry door! I definitely recommend this place!

My folks have stayed here a few times while visiting me and the family, and it's been great every time.