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

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Our top choices for Hampshire County holiday rentals

A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

1. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,756 reviews)
"This was a fantastic property to end our New England trip!"
United States
Adrianne
The price is ฿2,685
฿3,366 total
includes taxes & fees
1 Nov - 2 Nov
Vacation Village in the Berkshires
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

2. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,212 reviews)
"Beautiful location. Easy access to local restaurants and hiking trails."
United States
Joel
The price is ฿2,892
฿3,977 total
includes taxes & fees
10 Nov - 11 Nov
Berkshire Mountain Lodge
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 ฿3,175
฿8,114 total
includes taxes & fees
19 Oct - 20 Oct
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"This was our 10 yr celebrating my girlfriend’s birthday at Vacation Village. It’s always a nice escape in the fall season. We usually get the larger “A” rooms as we want the in room jacuzzi. This time I got the same larger room but it was a “C” unit. It was a bit smaller all around. And the bed was a small queen instead of the larger king bed. Overall nice. But I will make sure to ask for an “A” unit next year. It is a great location right across the street from Jiminey Peak."
Robert 2-night trip
Posted 3 hours ago
Vacation Village in the Berkshires

Find out more about Hampshire County

Vacation Apartments in Hampshire County

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