A red barn with a metal roof, surrounded by a snow-covered landscape and a wooden fence.

Hampshire County Holiday Rentals

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Our top choices for Hampshire County holiday rentals

A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,223 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
The price is S$151
includes taxes & fees
22 Nov - 23 Nov
Berkshire Mountain Lodge
An outdoor patio with a table and chairs, a grill, and a large house in the background.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,780 reviews)
"We had an amazing stay."
United States
Luke
The price is S$129
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A two-story house with a front porch, a sign reading "Victory Residence," and the address "1785."

3. Modern Studio Ideal for Traveling Professionals

Modern Studio Ideal for Traveling Professionals
3.0 star property
Holyoke
The price is S$304
includes taxes & fees
2 Nov - 3 Nov
Modern Studio Ideal for Traveling Professionals
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hampshire County Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We've stayed at Berkshire Mountain Lodge in October a number of times now, and we really enjoy the property. The rooms are well-appointed, very clean, and quite comfortable. We appreciate the free washers and dryers as well as the many other amenities, and you cannot beat the location. There's a supermarket down the driveway and across the street and an excellent specialty grocer--Guido's Market--just down the road. We highly recommend this property. The District Restaurant in Pittsfield is excellent. We've also seen several great plays at Barrington Theatre Company. The area is loaded with historical and cultural activities. We like the proximity to Lenox and the Edith Wharton mansion as well as The Clark art museum in Williamstown, both of which have lovely grounds/gardens typically exhibiting sculptures. There are also abundant outdoor activities and opportunities for hiking and lovely scenic drives. This was a good year for fall color, and the red maples were glorious! It's a short ride to Vermont where we checked out Mt. Equinox for the first time. Highly recommend the drive to the top on a sunny, clear day."
Nancy C 4-night trip
Posted 7 hours ago
Berkshire Mountain Lodge