Cheshire
Travel Guide
Visit Cheshire
Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
The price is S$152 per night from 17 Jun to 18 Jun
S$152
17 Jun - 18 Jun
includes taxes & fees
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,819 reviews)
"Had and amazing time my son loves it"
Reviewed on 10 Jun, 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
The price is S$193 per night from 22 Jun to 23 Jun
S$193
22 Jun - 23 Jun
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 ...
9/10 Wonderful! (1,006 reviews)
"Property being totally updated"
Reviewed on 11 Jun, 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
The price is S$222 per night from 17 Jun to 18 Jun
S$222
17 Jun - 18 Jun
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (650 reviews)
"Great place for a family."
Reviewed on 9 Jun, 2025
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
276 Brodie Mountain Rd, Williamstown, MA
Stay at this 3-star family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,819 reviews)
"Had and amazing time my son loves it"
Reviewed on 10 Jun, 2025
Jiminy Peak Mountain Resort
37 Corey Rd, Hancock, MA
Stay at this 3-star ski condo in Hancock. Enjoy free parking, 2 restaurants, and 2 bars/lounges. Our guests praise the property condition in our reviews. Popular ...
8.2/10 Very Good! (933 reviews)
"Summer stay not during ski season. Staff very helpful, welcoming, friendly. Room was clean and nice although some people might consider the main lodging building where I stayed would be outdated. But it was a very good experience all around. Beautiful natural surroundings all around the area so it’s ..."
Reviewed on 9 Jun, 2025
The Ponds at Foxhollow
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo 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! (121 reviews)
"A good place for vacation that you can enjoy and rest. Very nice and safe place."
Reviewed on 14 May, 2025
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.
Popular places to visit
St Mary's of the Assumption Church
Learn about the local history of Cheshire with a stop at St Mary's of the Assumption Church. Discover the area's mountain views or seek out its ski slopes.