Guesthouse vacation rentals in The Berkshires

Have stayed at Judy’s Airbnb multiple times over past several years. It is a go-to spot for peaceful, quiet relaxation and effortless stays. My young daughter visits with me sometimes as well and enjoys this stay as well. The space is simple and comfortable, a great value. Judy is a friendly and considerate host.

An incredibly charming, rustic, simple and comfortable small cottage, in a gorgeous rural setting. Just as advertised. It was perfect. Right across the road is Tivoli Bays, with beautiful trails for walking and hiking, and a small waterfall too. If you like, it's just a short walk to Broadway, the main strip in the village of Tivoli. You'll find a few restaurant options, a small market, sandwich shop, excellent coffee, and homemade ice cream. I met Yuko who couldn't be nicer and was a pleasure to chat with. A great experience all around - highly recommend booking a stay!

What a wonderful and unique space. A wide open room with a cozy bed area. The kitchen is well appointed as well. Just a short walk to Northampton's downtown but quiet with lovely gardens all around.

A cozy spot that comfortably houses three adults, it's right on the river so it's perfect for fishing. While it feels remote, there are amenities close by like restaurants and grocery stores. And Bruce was a fantastic host, very friendly and helpful. I have no doubt we'll return.

stayed three nights, very unique and lovely place! Beautiful Vermont surroundings, friendly animals, plus lots of chicken action! Very cozy space. Friendly and communicative hosts, Erica showed us around and told us all about the chickens.

Happy to be back at this lovely Airbnb! Clean and cozy as always with an extremely comfortable bed and sweet tub. Rochelle was instantly responsive when I reached out with an issue with the door lock when entering (due only to the very cold day). She gave us an easy tip and we were in in less than two minutes. This is a great place to stay.

Joni’s Airbnb is one of a kind! It’s beautiful appointed and truly captures the spirit of Woodstock. It had all of the amenities my husband and I needed, plus extra little touches that made us feel right at home. Not only was the house somewhere we felt we could have stayed for weeks, but the location was unmatched. Just a 5 minute walk into town, everything was available to us without ever needing our car. Joni was an amazing and generous host - her recommendations and proactive communication made us feel comfortable and well taken care of. We couldn’t recommend an Airbnb more!

Mary’s place was lovely. Cozy and very comfortable for our stay. It was a bit chilly (unseasonably) but Mary proactively remedied with space heaters before we arrived. All was great. Mary and Christoph were delightful hosts.

beth was wonderful. the place was great. she was so sweet and kind and made sure we had a great weekend. would definitely recommend. the pond with fish was fun to feed them. the little recommendations book she made was very helpful. we were there for an event over the weekend and it was very relaxing and we enjoyed our time.

The house is very comfortable and feels like home. The kitchen is spacious and well-equipped — a great experience for cooking. There’s a peaceful courtyard that’s perfect for calming your mind or reading a book. One night, we even spotted a bear from the window! It’s a great location, and don’t worry — the bears are vegetarian. Elisa and Mickey are very kind and responsive. They’ll even create a personalized list to help you explore the town, even if you’re not familiar with the area. You can shop at Taft Farm — my favorite local farm. Cooking at the house really made it feel like home, and also “farm to table” experience. Thank you!

Great experience! 2 wineries within 1 mile. Close to great hiking. William, was very accommodating with check in & check out time. Would highly recommend staying here. Very cute , clean and comfortable with get amenities.

John and Molly were fantastic hosts - responsive, friendly and extremely accommodating. The space was beautiful and matched descriptions + photos! It’s in a central location in downtown Toga - close to most restaurants, bars and shops.

My husband and I arrived late, around 9:30pm, because we had commuted after work in NYC. Everything was impeccable. The home is perfect in some many ways. We felt very comfortable and got an amazing night's sleep. The following more we had to head out early to pick our daughter up from Binghamton. She stayed with us on our second night. Nicolette's and Tim's Tiny Horse Barn is so perfect. It is exact amount of space we needed. Even though the space is space, there were 5 tissue boxes in perfect locations. This may seem a small thing to some. But if you have allergies, it is SO appreciated. The kitchen was equipped with keurig coffee pods, creamers, sugar, tea kettle and more than everything we needed. Equally the bathroom was perfect. The beds were super comfortable as was the temperature. There were plenty of great restaurants nearby. The attention to detail is amazing. Everywhere there are little hints of horses, but not in an overwhelming way. We actually are having book sent :)

We had a great night hear. It is a wonderful town. We were at an event at Williams College and were able to easily walk there. There are plenty of shops and restaurants along the way. The area is beautiful. The space is amazing. Perfect for couples. We appreciated the treats and milk. The host was responsive to the only question we had and answered everything immediately. The instructions are exquisite and well planned. If you are in the area this is a great find.

Our stay at Kelly’s place was fantastic! We stayed here last year and loved it so much, we decided to stay again this year. It was very cozy and we felt right at home. Everything was very clean and Kelly thought of all the little details that made our stay that much more pleasant & relaxing. Her place is a peaceful oasis, very quiet & private and the beach access was our favorite. Kelly was super responsive and allowed us to extend our stay for an extra day so we could enjoy one more day in the area. Overall, I would highly recommend staying here.

We had a great overnight at cozy duck cottage. The cottage has the basic necessities with beautiful surroundings. We especially enjoyed the ducks who were very friendly! Would stay again!

We were stunned by how magical this place was with all it's uniqueness of historic house. Spotless clean, spacious, very friendly owners. Our kids loved running around the back yard and playing board games that were provided. We would definitely come back, the only thing we regret is that we couldn't stay for longer, the area is very picturesque. many thanks!

My boyfriend and I booked last minute trip! That turned out magical ! The view was priceless, the hot tub was large and had message features, hammock was great. Suite is adorable and very clean. You’re literally on top of a mountain with no neighbors and surrounded by nature. Very private ! We caught an amazing view day and night on a clear sunny day and then a lightning storm in the mist! We missed our farm friends as soon as we left. Accurate listing ! Highly recommend 4wheel drive !

The location is very peaceful and serene and the hosts are very thoughtful. It was a wonderful stay, thank you so much for having us!

The cottage was the perfect little get away! Tucked away in nature with plenty of scenes to enjoy nearby. Easily accessible to Kingston and Woodstock to dine out and shop. The cottage was clean and organized. Would definitely come back!

The Eco Cottage was a perfect, tiny gem tucked away in the middle of the beautiful green woods. It was so private, peaceful, and serene. It truly felt like my own little retreat and since I was there to go on a retreat, this was the perfect place to lay my head at night. I loved walking the trails and wow, the pool, which looked so inviting (even if it was a bit too chilly to use this time!). Everything was clean, and the instructions were clear and easy to follow. Hosts checked in regularly but gave me my privacy. I really enjoyed my stay SO MUCH and will absolutely be booking here again the next time I’m in the area. Highly recommend!

Great place to stay in the Cooperstown area. Under an hour drive to HoF through pastoral country. Got a decent Pizza in Ft Plain from Papa Joes. If I was visiting the area again and didn’t want to stay in Cooperstown, I’d definitely come back here.

Easy to find, key pad entry, clean. Graham left some fresh eggs from his hens..nice touch. Quiet spot in a natural setting.

Very lovely space. Felt very cozy and was in such a convenient location. Absolutely loved all that was offered! Would recommend to friends & family!