Cheshire Holidays
Book a Hotel + Flight or Car together to unlock savings
Top hotels in Cheshire
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is 3.200.582 ₫ per night from 23 Jun to 24 Jun
3.200.582 ₫
4.162.882 ₫ total
23 Jun - 24 Jun
includes taxes & fees
9/10 Wonderful! (961 reviews)
"Water pressure in shower overwhelmingly strong"
Reviewed on 2 Jun 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is 3.326.279 ₫ per night from 15 Jun to 16 Jun
3.326.279 ₫
4.004.108 ₫ total
15 Jun - 16 Jun
includes taxes & fees
8.8/10 Excellent! (2,388 reviews)
"While traveling in the area for summer we found Vacation Village. Great jump off point, great amenities, helpful staff, nice set up inside the condo, pots, pans, utensils, glassware, other cooking utensils in good shape. Private decks are a nice touch. Best bargain in the area by far!!! Will be ..."
Reviewed on 1 Jun 2026
Berkshires Untold
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is 3.285.611 ₫ per night from 7 Jun to 8 Jun
3.285.611 ₫
3.670.028 ₫ total
7 Jun - 8 Jun
includes taxes & fees
9/10 Wonderful! (968 reviews)
"Very nice hotel. Highly recommend the restaurant."
Reviewed on 2 Jun 2026
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.
