Guest house holiday rentals in The Berkshires

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!

Nice ground floor apartment across the street from the beach and 2 blocks from the state park. Love the outdoors. And Delores and her brother were amazing. Friendly, responsive, and helpful.

There is not enough to say about the pristine beauty that is Loraine’s cabin. The instructions were helpful in navigating into the property and lights were turned on as it was dark to assure my comfortable arrival. The cabin feels like a nurturing home and is equipped with comforts and small touches. The bed was neatly made and felt like a picture walking in to see it. The stairs are cabin stairs and there is caution to take your time and step gently. Seemingly every question was answered with small notes around the cabin and a detailed welcome book. The care and attention to detail was perfection in a stay. I only wish I had been on a longer trip to fully enjoy the grounds and the surroundings. It was easy to feel at home and welcome with Loraine and Dean as hosts.

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

absolutly amazing stay, super nice hostess we loved the decorations and they provided alot of things and services, also the epiq peoples book was a really cute idea. we will forsure be coming again soon!

We hebben genoten van onze 2 nachten in de barn. Na de hectiek van een aantal dagen NYC wat het heerlijk bijkomen in deze mooie omgeving. Prachtige natuur en heerlijke restaurants zijn vlakbij. De barn zelf is van alle gemakken voorzien. Een geweldige speelzolder voor de kinderen, heerlijke bedden met superzacht linnen en een fijne keuken waar niks aan ontbreekt. Een prachtige tuin waar we heerlijk hebben kunnen voetballen. Onze zoon kreeg zelfs een privé voetbalclinic van Chris! Beth en Chris zijn super vriendelijk en behulpzaam. Bedankt!

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!

Carolyn & Dan’s place was wonderful. We came with our 2 year old toddler, the place had everything we needed (crib, high hair, books for kids, even toys!). Their home is soooo beautifully decorated with thoughtful touches everywhere, and extremely clean and welcoming. The endless grass outside is just stunning. They communicated with us all throughout if we needed to ask for recommendations etc, and check in was easy! I highly recommend their place. Loved it.

Beautiful stay! Came to CT with 2 winterstorms back to back and below freezing temps. The place was cozy and warm the whole time! A great place to relax and watch the tide come in and out. And the "throne" room has a great view!

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!

This is a gorgeous guest house with a lovely view of the lake. Didn’t get to try the sauna but appreciated that it was available all hours. Shower and bed were nice! We traveled here on bike while going from Poughkeepsie to NYC on the Empire State Trail. The house is close to the trail and they gave us good bike directions. Great place to stop to split up the 100 mile journey - right in the middle!

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!!

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 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!

Fantastic place for a weekend getaway! Gail is a lovely host and very responsive. You have one room as shown in the picture, and a separate bathroom with a shower, towels, and toilets. It's a 20 second walk away from the main room. We visited during autumn and the trees were beautiful. You can use a grill and fireplace, as well as a boat on the small lake. Can highly recommend!

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.

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!

We had such a great long stay at Sarah and Chris's place, mostly skiing but also hiking and touring. The apartment is better than the photos, and the beds and furniture are very comfy. We ended up cooking quite a bit, and the kitchen was perfectly equipped for our needs. We loved having great food shopping minutes away and we also took advantage of the nearby spa. Sarah and Chris were very helpful and made sure all was good with our stay. It was perfect! We hope to return again.

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