Cheshire Travel Guide
Tourist Guide
Visit Cheshire
Hotel Downstreet, an Ascend Collection Hotel
40 Main St North Adams MA
The price is NZ$335 per night from 30 June to 1 July
NZ$335
per night
30 June - 1 July
Stay at this business-friendly hotel in North Adams. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (1,008 reviews)
"No real breakfast"
Reviewed on 21 June 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is NZ$248 per night from 23 June to 24 June
NZ$248
per night
23 June - 24 June
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,004 reviews)
"The only tiny complaint is that there was no maple syrup for the waffles. Everything else was fantastic!"
Reviewed on 21 June 2026
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
The price is NZ$236 per night from 24 June to 25 June
NZ$236
per night
24 June - 25 June
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
8.8/10 Excellent! (2,406 reviews)
"Everything was top. Can't think of anything to improve. Hope we can return, certainly we'll try"
Reviewed on 22 June 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.
Vacation Village in the Berkshires
276 Brodie Mountain Rd Williamstown MA
Stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness centre and a 24-hour front desk. Our guests praise the helpful staff in their ...
8.8/10 Excellent! (2,406 reviews)
"Everything was top. Can't think of anything to improve. Hope we can return, certainly we'll try"
Reviewed on 22 June 2026
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham VT
Stay at this apartment in Whitingham. Enjoy free breakfast, a sauna and laundry facilities. Popular attractions Harriman Reservoir and Readsboro Community Library ...
9.8/10 Exceptional! (6 reviews)
"We had a wonderful Memorial Day weekend here with our two young daughters. We enjoyed the gorgeous views, the hot tub, and the very comfortable beds. There was plenty of space for four people. Chris responded very quickly to any questions we had. A very unique home that we are happy to have made ..."
Reviewed on 25 May 2026
Huttopia Berkshires
312 Kittle Rd Williamstown MA
Stay at this campsite in Williamstown. Enjoy free parking, breakfast (surcharge) and a picnic area. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
9.4/10 Exceptional! (10 reviews)
"Excelente servicio"
Reviewed on 8 Mar 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.
Popular places to visit
St Mary's of the Assumption Church
St Mary's of the Assumption Church is just one of the places to see in Cheshire, so why not enjoy the other things to explore during your travels? Discover the area's mountain views or seek out its ski slopes.
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- Colrain Hotels
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- Visit Charlemont
- Visit Western Massachusetts
- Visit The Berkshires
- Visit Leyden
- Visit Great Barrington
- Visit Hatfield
- Visit West Stockbridge
- Visit Middlefield
- Visit Amherst
- Visit Hawley
- Visit Williamstown
- Visit Tyringham
- Visit North Adams
- Visit Otis
- Charlemont Holidays
- Goose Pond Reservation
- Massachusetts Museum of Contemporary Art
- Otis Holidays
- G. William Pitt House and Collection
- Pittsfield Holidays
- North Adams Holidays
- National Shrine of the Divine Mercy
- Sterling and Francine Clark Art Institute
- Arthur A. Smith Covered Bridge
- Cheshire Holidays
- Williams College
- Norman Rockwell Museum
- All inclusive Holiday Packages Western Massachusetts
- Beach Holiday Packages Western Massachusetts
