Title: Cheshire Travel Guide: Best of Cheshire, Massachusetts Travel 2025 | Expedia.co.uk [Hotels in Cheshire](https://expedia.co.uk/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Holiday Rentals in Cheshire](https://expedia.co.uk/Cheshire-Holiday-Rentals.d6005398.Travel-Guide-HolidayRentals)[Flights to Cheshire](https://expedia.co.uk/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[Cheshire Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Cheshire.d6005398.Car-Hire-Guide)[Cheshire Holidays](https://expedia.co.uk/Cheshire.d6005398.Holidays-City-Breaks) # Cheshire Travel Guide ## Tourist Guide ![Photo by Ed Gaffny](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Ed Gaffny](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg) ![Photo by Chris Addams](https://mediaim.expedia.com/destination/2/fa88c56ac508d2b7e0956184ee96b6cf.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Chris Addams](https://mediaim.expedia.com/destination/2/fa88c56ac508d2b7e0956184ee96b6cf.jpg) ![Photo by Chris Addams](https://mediaim.expedia.com/destination/2/fca6f90b8c90b2ba024338672184667a.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Chris Addams](https://mediaim.expedia.com/destination/2/fca6f90b8c90b2ba024338672184667a.jpg) ![Photo by Chris Addams](https://mediaim.expedia.com/destination/2/53a79e170bf1208fd67dbef187d0ba8f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Chris Addams](https://mediaim.expedia.com/destination/2/53a79e170bf1208fd67dbef187d0ba8f.jpg) ![Photo by Chris Addams](https://mediaim.expedia.com/destination/2/0bbeb5c343ebcf670623da277b2a855b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) [Photo by Chris Addams](https://mediaim.expedia.com/destination/2/0bbeb5c343ebcf670623da277b2a855b.jpg) ## Visit Cheshire Things to do - Top hotels in Cheshire - Top Holiday Rentals in Cheshire ![Harbour House Inn](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Harbour House Inn 725 North State Road, Cheshire, MA £192 4 Dec - 5 Dec includes taxes & fees Stay at this 3.5-star B&B in Cheshire. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Adams Theater and Mount Greylock State Reservation ... 9.6/10 Exceptional! (38 reviews) The owner Brandi was outstanding, friendly, she made us fresh homemade breakfast each morning, which the best. Will differently stay there again. Wonderful place and people. Reviewed on 12 Sept 2025 [](https://expedia.co.uk/Hotel-Search?startDate=04%2F12%2F2025&endDate=05%2F12%2F2025&selected=17326568&PinnedHotelID=17326568&HadPinnedHotel=true®ionId=6005398) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd, Williamstown, MA £86 12 Nov - 13 Nov includes taxes & fees 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! (2,124 reviews) We loved almost everything, but they need to replace sofa, armchair and the bed in this unit. Too old. The sofa and armchair have bad smell of very old furniture. Reviewed on 7 Nov 2025 [](https://expedia.co.uk/Hotel-Search?startDate=12%2F11%2F2025&endDate=13%2F11%2F2025&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=6005398) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Downstreet, an Ascend Collection Hotel 40 Main St, North Adams, MA £116 11 Dec - 12 Dec includes taxes & fees Stay at this 3-star business-friendly hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff ... 8.6/10 Excellent! (1,003 reviews) Very clean and inviting Hotel located in downtown area. Very walkable area. Parking was free. Front desk very friendly and helpful. Would stay again. Reviewed on 3 Nov 2025 [](https://expedia.co.uk/Hotel-Search?startDate=11%2F12%2F2025&endDate=12%2F12%2F2025&selected=2943&PinnedHotelID=2943&HadPinnedHotel=true®ionId=6005398) [See all 997 properties in Cheshire](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=12%2F11%2F2025&endDate=13%2F11%2F2025®ionId=6005398) 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](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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! (2,124 reviews) We loved almost everything, but they need to replace sofa, armchair and the bed in this unit. Too old. The sofa and armchair have bad smell of very old furniture. Reviewed on 7 Nov 2025 [](https://expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Jiminy Peak Mountain Resort](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/cf8c8830_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 hot tubs. Our guests praise the property condition in their reviews. Popular ... 8.2/10 Very Good! (984 reviews) This is our second time staying here. We love the property, the suites work for us as there is a bedroom which is separate from the living space. There are plenty of things to do on the property and in the surrounding area. Mt. Greylock, antiquing, great breakfast spots! The Country Store on the ... Reviewed on 5 Oct 2025 [](https://expedia.co.uk/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information) ![Huttopia Berkshires ](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 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 ... 10/10 Exceptional! (7 reviews) Healthy food too! Reviewed on 20 Oct 2025 [](https://expedia.co.uk/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) [See all properties in Cheshire](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6005398&sort=VACATION_RENTAL) 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. ## Check Cheshire hotel availability [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-11-11&endDate=2025-11-12) [Tonight](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-11-11&endDate=2025-11-12) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-11-11&endDate=2025-11-12) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-11-11&endDate=2025-11-12)[11 Nov - 12 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-11-11&endDate=2025-11-12) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-11-12&endDate=2025-11-13) [Tomorrow night](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-11-12&endDate=2025-11-13) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-11-12&endDate=2025-11-13) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-11-12&endDate=2025-11-13)[12 Nov - 13 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-11-12&endDate=2025-11-13) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [This weekend](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025)[14 Nov - 16 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=14%2F11%2F2025&endDate=16%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [Next weekend](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) [](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025)[21 Nov - 23 Nov](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=21%2F11%2F2025&endDate=23%2F11%2F2025) ### 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. [](https://expedia.co.uk/St-Marys-Of-The-Assumption-Church-Cheshire.d553248621532665539.Attraction) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - [Adams Hotels](https://www.expedia.co.uk/Adams-Hotels.d6005393.Travel-Guide-Hotels) - [Guest Houses in Ashuwillticook Rail Trail](https://www.expedia.co.uk/Ashuwillticook-Rail-Trail-Guest-Houses.d811531152953708544-aaGuestHouses.Travel-Guide-Accommodation) - [Cummington Hotels](https://www.expedia.co.uk/Cummington-Hotels.d183324.Travel-Guide-Hotels) - [Dalton Hotels](https://www.expedia.co.uk/Dalton-Hotels.d6911.Travel-Guide-Hotels) - [Berkshire County Hotels](https://www.expedia.co.uk/Destinations-In-Berkshire-County.d553248635083901436.Hotel-Destinations) - [Drury Hotels](https://www.expedia.co.uk/Drury-Hotels.d3000748865.Travel-Guide-Hotels) - [Florida Hotels](https://www.expedia.co.uk/Florida-Hotels.d553248634999031091.Travel-Guide-Hotels) - [Hancock Hotels](https://www.expedia.co.uk/Hancock-Hotels.d112303.Travel-Guide-Hotels) - 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[Pittsfield Hotels](https://www.expedia.co.uk/Pittsfield-Hotels.d9478.Travel-Guide-Hotels) - [B&B in Savoy](https://www.expedia.co.uk/Savoy-Bed-And-Breakfasts.d6005417-aaBedAndBreakfasts.Travel-Guide-Accommodation) - [Hilton Hotels in Savoy](https://www.expedia.co.uk/Savoy-Hotels-Hilton-Hotels.0-0-d6005417--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Savoy Hotels](https://www.expedia.co.uk/Savoy-Hotels.d6005417.Travel-Guide-Hotels) - [Washington Hotels](https://www.expedia.co.uk/Washington-Hotels.d553248634998690770.Travel-Guide-Hotels) - [Hotels near Williams College Museum of Art](https://www.expedia.co.uk/Williams-College-Museum-Of-Art-Hotels.0-l6091837-0.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Williamstown](https://www.expedia.co.uk/Williamstown-Hotels-Gay-Friendly-Hotel.0-0-d7859-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Williamstown](https://www.expedia.co.uk/Williamstown-Hotels-Luxury-Hotel.0-0-d7859-tLuxuryHotel.Travel-Guide-Filter-Hotels) - 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[Visit Ashuwillticook Rail Trail](https://www.expedia.co.uk/Ashuwillticook-Rail-Trail.dx811531152953708544) - [Visit Becket](https://www.expedia.co.uk/Becket.dx6005395) - [Visit Berkshire County](https://www.expedia.co.uk/Berkshire-County.dx553248635083901436) - [Visit Blandford](https://www.expedia.co.uk/Blandford.dx80625) - [Visit Colrain](https://www.expedia.co.uk/Colrain.dx91560) - [Cummington Holidays](https://www.expedia.co.uk/Cummington.d183324.Holidays-City-Breaks) - [Visit Cummington](https://www.expedia.co.uk/Cummington.dx183324) - [Drury Holidays](https://www.expedia.co.uk/Drury.d3000748865.Holidays-City-Breaks) - [Visit East Longmeadow](https://www.expedia.co.uk/East-Longmeadow.dx6005400) - [Visit Goshen](https://www.expedia.co.uk/Goshen.dx109585) - [Visit Great Barrington](https://www.expedia.co.uk/Great-Barrington.dx110336) - [Visit Greenfield](https://www.expedia.co.uk/Greenfield.dx8027) - [Hancock Holidays](https://www.expedia.co.uk/Hancock.d112303.Holidays-City-Breaks) - [Visit Hancock](https://www.expedia.co.uk/Hancock.dx112303) - [Lanesborough Holidays](https://www.expedia.co.uk/Lanesborough.d6005408.Holidays-City-Breaks) - [Lenox Holidays](https://www.expedia.co.uk/Lenox.d8587.Holidays-City-Breaks) - [Visit Lenox](https://www.expedia.co.uk/Lenox.dx8587) - [Visit Longmeadow](https://www.expedia.co.uk/Longmeadow.dx6005409) - [Visit Mill River](https://www.expedia.co.uk/Mill-River.dx3000748895) - [New Ashford Holidays](https://www.expedia.co.uk/New-Ashford.d183333.Holidays-City-Breaks) - [North Adams Public Library](https://www.expedia.co.uk/North-Adams-Public-Library-North-Adams.d553248621532666701.Attraction) - [Visit North Adams](https://www.expedia.co.uk/North-Adams.dx9137) - [Visit Northampton](https://www.expedia.co.uk/Northampton.dx9187) - [Visit Orange](https://www.expedia.co.uk/Orange.dx6348110) - [Visit Pittsfield](https://www.expedia.co.uk/Pittsfield.dx9478) - [Visit Sandisfield](https://www.expedia.co.uk/Sandisfield.dx6005416) - [Savoy Holidays](https://www.expedia.co.uk/Savoy.d6005417.Holidays-City-Breaks) - [Visit Shelburne Falls](https://www.expedia.co.uk/Shelburne-Falls.dx6294302) - [Visit Southampton](https://www.expedia.co.uk/Southampton.dx6005419) - [Visit Springfield](https://www.expedia.co.uk/Springfield.dx6047669) - [Visit Stockbridge](https://www.expedia.co.uk/Stockbridge.dx162575) - [Visit Sunderland](https://www.expedia.co.uk/Sunderland.dx3000441543) - [Visit The Berkshires](https://www.expedia.co.uk/The-Berkshires.dx6047665) - [Visit Turners Falls](https://www.expedia.co.uk/Turners-Falls.dx6005422) - [Visit West Stockbridge](https://www.expedia.co.uk/West-Stockbridge.dx173346) - [Visit Western Massachusetts](https://www.expedia.co.uk/Western-Massachusetts.dx6234063) - [Williams College](https://www.expedia.co.uk/Williams-College-Williamstown.d6091833.Attraction) - [Visit Williamstown](https://www.expedia.co.uk/Williamstown.dx7859) - [Windsor Holidays](https://www.expedia.co.uk/Windsor.d6005427.Holidays-City-Breaks) - [Car hire Adams](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Adams.d6005393.Car-Hire-Guide) - [Car hire Lenox](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lenox.d8587.Car-Hire-Guide) - [Car hire near Pittsfield State Forest](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Pittsfield-State-Forest.d6339854.Car-Hire-Guide) - [Car hire Pittsfield](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Pittsfield.d9478.Car-Hire-Guide) - [Car hire Williamstown](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Williamstown.d7859.Car-Hire-Guide) - [Florida Holiday Rentals](https://www.expedia.co.uk/Florida-Holiday-Rentals.d553248634999031091.Travel-Guide-HolidayRentals) - [Peru Holiday Rentals](https://www.expedia.co.uk/Peru-Holiday-Rentals.d553248634999167831.Travel-Guide-HolidayRentals) - Cities near Cheshire - Places of interest - [Tanglewood Music Center](https://expedia.co.uk/Tanglewood-Music-Center-Lenox.d503292.Attraction) - [Green Mountain National Forest](https://expedia.co.uk/Green-Mountain-National-Forest-Vermont.d6115904.Attraction) - [Williams College](https://expedia.co.uk/Williams-College-Williamstown.d6091833.Attraction) - [Norman Rockwell Museum](https://expedia.co.uk/Norman-Rockwell-Museum-Stockbridge.d6091839.Attraction) - [Ventfort Hall Mansion and Gilded Age Museum](https://expedia.co.uk/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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