The Berkshires which includes snowboarding and snow

Holiday Homes in The Berkshires

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Featured Holiday Homes in The Berkshires and around

Our top choices for The Berkshires holiday homes

"Host was very friendly and helpful. House was absolutely adorable and decorated well. Plenty of parking. Beautiful, well-maintained property. Great for hikes. Lovely fire pit area and lots of wood. Very convenient location to recreation in The Berkshires. I would stay here again. "

includes taxes & fees

16 Sept - 17 Sept

"Very clean and spacious! We enjoyed our stay with our small pup!"

includes taxes & fees

11 Sept - 12 Sept

"Enjoyed our stay!!!"

"My boyfriend and I loved our stay at the cottage. Nicole was very easy to communicate with. The house was cozy and had everything we needed. Even though it rained all weekend, the hot tub and games made up for it. Thank you, Nicole! Can't wait to come back!"

"We loved it! Lots of local hiking trails and a wonderful relaxing place."

includes taxes & fees

3 Sept - 4 Sept

"Claudia is such a considerate and thoughtful host! We felt so welcome and at ease."

includes taxes & fees

4 Sept - 5 Sept

"Kind and responsive host."

includes taxes & fees

1 Sept - 2 Sept

"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "

includes taxes & fees

1 Oct - 2 Oct

"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "

includes taxes & fees

9 Sept - 10 Sept

"Great location, very clean and well appointed with everyth"

"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."

includes taxes & fees

1 Sept - 2 Sept

"Very kinda hosts, and wonderful house."

includes taxes & fees

3 Sept - 4 Sept

"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "

includes taxes & fees

14 Sept - 15 Sept