A lake with a rocky shoreline and a forested island.

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Western Massachusetts 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, (1,205 reviews)
"Friendly hotel staff."
United States
Kathleen
The price is ฿2,877
฿3,964 total
includes taxes & fees
9 Nov - 10 Nov
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,743 reviews)
The price is ฿2,697
฿3,381 total
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 ฿3,189
฿8,149 total
includes taxes & fees
20 Oct - 21 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 Western Massachusetts Hotel Reviews

The Yankee Inn

The Yankee Inn

10/10 Excellent
"This is a gem of a small hotel/motel. Super comfortable rooms, updated bathrooms, and well done self serve breakfast included. Also has an indoor pool and an outdoor pool during the season. And a very nice hiking trail off of the back. An excellent change from the Run of the middle courtyard Marriott!"
Kimberly 2-night trip
Posted 1 hour ago
The Yankee Inn

Find out more about Western Massachusetts

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Look no further and take a look at our great range of rental properties in Western Massachusetts!