The Berkshires featuring snowboarding and snow

Holiday Homes in The Berkshires

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Featured Holiday Homes in The Berkshires

"We enjoyed our stay. Excellent location to explore Western Mass!"

includes taxes & fees

28 Oct - 29 Oct

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

includes taxes & fees

6 Oct - 7 Oct

"Kind and responsive host."

includes taxes & fees

6 Oct - 7 Oct

"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."

includes taxes & fees

6 Oct - 7 Oct

"Enjoyed our stay!!!"

includes taxes & fees

3 Nov - 4 Nov

includes taxes & fees

28 Oct - 29 Oct

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

includes taxes & fees

5 Oct - 6 Oct

"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

2 Nov - 3 Nov

"The property was centrally located for skiing, and was a comfortable stay."

includes taxes & fees

13 Oct - 14 Oct

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

includes taxes & fees

28 Oct - 29 Oct

"We had a wonderful stay, thank you! "

includes taxes & fees

5 Oct - 6 Oct

"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."

includes taxes & fees

5 Oct - 6 Oct

"Amazing Inn. Cozy and everything we needed. "

includes taxes & fees

21 Oct - 22 Oct

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

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16 Oct - 17 Oct

"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"

includes taxes & fees

13 Oct - 14 Oct

"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...

includes taxes & fees

2 Nov - 3 Nov