Cheshire, MA

Travel Guide

A lake surrounded by autumn-colored trees and hills.
A lake with lily pads and reeds, surrounded by autumn-colored trees and hills.
A lake surrounded by autumn-colored trees with a clear sky.
A rural road with a double yellow line, surrounded by green fields and trees, under a partly cloudy sky.
A frozen lake with a group of ducks swimming in the center.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
The price is AED 342 per night from Aug 23 to Aug 24
AED 342
AED 422 total
23 Aug - 24 Aug
includes taxes & fees
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
Vacation Village in the Berkshires
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is AED 585 per night from Aug 9 to Aug 10
AED 585
AED 654 total
9 Aug - 10 Aug
includes taxes & fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9.2/10 Wonderful! (1,009 reviews)
"Great standard hotel room. Clean and responsive housekeeping."

Reviewed on 6 August 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AED 393 per night from Aug 30 to Aug 31
AED 393
AED 521 total
30 Aug - 31 Aug
includes taxes & fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,045 reviews)
"Very nice space with a full kitchen. You can definitely stay here for a week comfortably. Personally, I didn’t think the bed or the pillows were that comfortable but other than that, it was great."

Reviewed on 7 August 2026

Berkshire Mountain Lodge
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.
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd Williamstown MA
Book a stay at this family-friendly aparthotel in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful ...
Vacation Village in the Berkshires
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,045 reviews)
"Very nice space with a full kitchen. You can definitely stay here for a week comfortably. Personally, I didn’t think the bed or the pillows were that comfortable but other than that, it was great."

Reviewed on 7 August 2026

Berkshire Mountain Lodge
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7 Lenox MA
Stay at this aparthotel in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Tanglewood Music Center and The Mount are located ...
8.6/10 Excellent! (145 reviews)
"Quiet property. Convenient location."

Reviewed on 2 August 2026

The Ponds at Foxhollow
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.

Stay near popular Cheshire attractions