Cheshire Travel Guide
Tourist Guide
Visit Cheshire
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 centre and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,836 reviews)
"The property was perfect for a getaway. 1 bedroom suite or more with balconies. Non heating Fireplace for aesthetics. The suite was a jack and Jill! Shower, but also a jet tub separate from shower. All dishes and cooking utensils that you needed. You can grill onsite or cook in your suite as take ..."
Reviewed on 24 Jun 2025
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Fully refundableReserve now, pay when you stay
The price is 3.860.773 ₫ per night from 30 Jun to 1 Jul
3.860.773 ₫
4.677.635 ₫ total
30 Jun - 1 Jul
includes taxes & fees
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business centre and a snack bar/deli. Our guests praise the helpful staff ...
9/10 Wonderful! (659 reviews)
Good for a girls trip!
"We loved the comfortable beds and ensuite bathrooms. The kitchen was well-equipped and common room was comfortable too. We didn't use any of the other amenities, but there were quite a few options that looked appealing. Convenient to Lenox which was our primary destination for dining and ..."
Reviewed on 21 Jun 2025
Best Western Plus Berkshire Hills Inn & Suites
1350 W Housatonic St, Pittsfield, MA
The price is 3.090.450 ₫ per night from 6 Jul to 7 Jul
3.090.450 ₫
3.452.033 ₫ total
6 Jul - 7 Jul
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (1,003 reviews)
"I loved everything about this hotel! It was PERFECT! This is my favorite hotel!"
Reviewed on 23 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 centre and a 24-hour front desk. Our guests praise the helpful staff ...
8.6/10 Excellent! (1,836 reviews)
"The property was perfect for a getaway. 1 bedroom suite or more with balconies. Non heating Fireplace for aesthetics. The suite was a jack and Jill! Shower, but also a jet tub separate from shower. All dishes and cooking utensils that you needed. You can grill onsite or cook in your suite as take ..."
Reviewed on 24 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 their reviews. Popular ...
8.2/10 Very Good! (937 reviews)
"Awesome place to vacation with family! Pool was a little small and not the cleanest."
Reviewed on 23 Jun 2025
The Ponds at Foxhollow
3 Foxhollow Drive Route 7, Lenox, MA
Stay at this 3-star condo in Lenox. Enjoy free Wi-Fi, free parking and a fitness centre. 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.
- Jiminy Peak Mountain Resort
- Williams College
- Green Mountain National Forest
- Mount Greylock
- Norman Rockwell Museum
- Jacob's Pillow
- Lee Premium Outlets
- Bousquet Ski Area
- Hancock Shaker Village
- Mount Greylock State Reservation Visitor Center
- Berkshire Botanical Garden
- Shakespeare and Company
- Ventfort Hall Mansion and Gilded Age Museum
- Bridge of Flowers
- Housatonic River
- Berkshire Museum
- Natural Bridge State Park
- Taconic Golf Club
- Goose Pond Reservation
- Colonial Theater
- Pyramid Lake