Title: Cheshire Travel Guide: Best of Cheshire, Massachusetts Travel 2026 | 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 ![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 £94 4 Jan - 5 Jan 2026 includes taxes & fees 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 ... 8.6/10 Excellent! (2,179 reviews) My stay was great with no problems. Reviewed on 19 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=04%2F01%2F2026&endDate=05%2F01%2F2026&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 £103 25 Jan - 26 Jan 2026 includes taxes & fees Stay at this business-friendly hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the ... 8.6/10 Excellent! (1,001 reviews) Courteous staff Reviewed on 19 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=25%2F01%2F2026&endDate=26%2F01%2F2026&selected=2943&PinnedHotelID=2943&HadPinnedHotel=true®ionId=6005398) ![The Williams Inn](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Williams Inn 101 Spring Street Williamstown MA £161 13 Jan - 14 Jan 2026 includes taxes & fees Stay at this business-friendly hotel in Williamstown. Enjoy free Wi-Fi, free parking and a fitness centre. Our guests praise the helpful staff in their reviews. ... 9.6/10 Exceptional! (550 reviews) Room was very clean. Didn’t have breakfast. Staff was friendly and check in was quick. Reviewed on 7 Dec 2025 [](https://expedia.co.uk/Hotel-Search?startDate=13%2F01%2F2026&endDate=14%2F01%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true®ionId=6005398) [See all 987 properties in Cheshire](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=27%2F12%2F2025&endDate=28%2F12%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 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 ... 8.6/10 Excellent! (2,179 reviews) My stay was great with no problems. Reviewed on 19 Dec 2025 [](https://expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Huttopia Berkshires ](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb_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) ![The Ponds at Foxhollow](https://images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/5c348ca4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Ponds at Foxhollow 3 Foxhollow Drive Route 7 Lenox MA Stay at this condo in Lenox. Enjoy free Wi-Fi, free parking and a fitness centre. Popular attractions The Mount and Wyndhurst Golf & Club are located ... 8.4/10 Very Good! (137 reviews) Great place Reviewed on 23 Dec 2025 [](https://expedia.co.uk/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.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 [Tonight ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-12-26&endDate=2025-12-27)[26 Dec - 27 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-12-26&endDate=2025-12-27) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-12-27&endDate=2025-12-28)[27 Dec - 28 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2025-12-27&endDate=2025-12-28) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)[26 Dec - 28 Dec](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=26%2F12%2F2025&endDate=28%2F12%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) - [Hawley Hotels ](https://www.expedia.co.uk/Hawley-Hotels.d3000438704.Travel-Guide-Hotels) - [Hinsdale Hotels ](https://www.expedia.co.uk/Hinsdale-Hotels.d6005406.Travel-Guide-Hotels) - [Hotels near Jiminy Peak Mountain Resort ](https://www.expedia.co.uk/Jiminy-Peak-Mountain-Resort-Hotels.0-l553248621532665536-0.Travel-Guide-Filter-Hotels) - [Lanesborough Hotels ](https://www.expedia.co.uk/Lanesborough-Hotels.d6005408.Travel-Guide-Hotels) - [B&B in Lenox ](https://www.expedia.co.uk/Lenox-Bed-And-Breakfasts.d8587-aaBedAndBreakfasts.Travel-Guide-Accommodation) - [Adults Only Resorts & in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Adults-Only-Resorts.0-0-d8587-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Budget-Hotels.0-0-d8587-tBudgetHotels.Travel-Guide-Filter-Hotels) - [Gay-Friendly Hotels in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Gay-Friendly-Hotel.0-0-d8587-tGayFriendlyHotel.Travel-Guide-Filter-Hotels) - [Hotels with Babysitting Services in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Hotel-With-Babysitting-Services.0-0-d8587-thotelwithbabysittingservices.Travel-Guide-Filter-Hotels) - [Hotels with Indoor Pools in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Hotels-With-Indoor-Pools.0-0-d8587-tHotelswithIndoorPools.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Lenox ](https://www.expedia.co.uk/Lenox-Hotels-Luxury-Hotel.0-0-d8587-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Lenox Hotels ](https://www.expedia.co.uk/Lenox-Hotels.d8587.Travel-Guide-Hotels) - [Hotels near Mount Greylock ](https://www.expedia.co.uk/Mount-Greylock-Hotels.0-l6091829-0.Travel-Guide-Filter-Hotels) - [New Ashford Hotels ](https://www.expedia.co.uk/New-Ashford-Hotels.d183333.Travel-Guide-Hotels) - [North Adams Hotels ](https://www.expedia.co.uk/North-Adams-Hotels.d9137.Travel-Guide-Hotels) - [Lodges in October Mountain State Forest ](https://www.expedia.co.uk/October-Mountain-State-Forest-Lodges.d6339856-aaLodges.Travel-Guide-Accommodation) - [Peru Hotels ](https://www.expedia.co.uk/Peru-Hotels.d553248634999167831.Travel-Guide-Hotels) - [Cheap Hotels in Pittsfield ](https://www.expedia.co.uk/Pittsfield-Hotels-Budget-Hotels.0-0-d9478-tBudgetHotels.Travel-Guide-Filter-Hotels) - [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) - [Pet-Friendly Hotels in Williamstown ](https://www.expedia.co.uk/Williamstown-Hotels-Pet-Friendly-Hotel.0-0-d7859-tPetFriendlyHotel.Travel-Guide-Filter-Hotels) - [Williamstown Hotels ](https://www.expedia.co.uk/Williamstown-Hotels.d7859.Travel-Guide-Hotels) - [Windsor Hotels ](https://www.expedia.co.uk/Windsor-Hotels.d6005427.Travel-Guide-Hotels) - [Hotels near Zoar Outdoor/Deerfield Valley Canopy Tours ](https://www.expedia.co.uk/Zoar-OutdoorDeerfield-Valley-Canopy-Tours-Hotels.0-l553248621561930011-0.Travel-Guide-Filter-Hotels) - [Flights to Florida ](https://www.expedia.co.uk/Cheap-Flights-To-Florida.d553248634999031091.Travel-Guide-Flights) - [Flights to Lanesborough ](https://www.expedia.co.uk/Cheap-Flights-To-Lanesborough.d6005408.Travel-Guide-Flights) - [Flights to Lenox ](https://www.expedia.co.uk/Cheap-Flights-To-Lenox.d8587.Travel-Guide-Flights) - [Flights to North Adams ](https://www.expedia.co.uk/Cheap-Flights-To-North-Adams.d9137.Travel-Guide-Flights) - [Flights to Pittsfield ](https://www.expedia.co.uk/Cheap-Flights-To-Pittsfield.d9478.Travel-Guide-Flights) - [Flights to Williamstown ](https://www.expedia.co.uk/Cheap-Flights-To-Williamstown.d7859.Travel-Guide-Flights) - [Flights from Peru ](https://www.expedia.co.uk/lp/flights/553248634999167831/flights-from-peru) - [Flights from Hinsdale ](https://www.expedia.co.uk/lp/flights/6005406/flights-from-hinsdale) - [Flights from Plainfield ](https://www.expedia.co.uk/lp/flights/6005414/flights-from-plainfield) - [Flights from Windsor ](https://www.expedia.co.uk/lp/flights/6005427/flights-from-windsor) - [Flights from Lenox ](https://www.expedia.co.uk/lp/flights/8587/flights-from-lenox) - [Flights from North Adams ](https://www.expedia.co.uk/lp/flights/9137/flights-from-north-adams) - [Flights from Pittsfield ](https://www.expedia.co.uk/lp/flights/9478/flights-from-pittsfield) - [Flights from New York (JFK) to Pittsfield (PSF) ](https://www.expedia.co.uk/lp/flights/jfk/psf/new-york-to-pittsfield) - [Visit Amherst ](https://www.expedia.co.uk/Amherst.dx5948) - [Ashuwillticook Rail Trail Holidays ](https://www.expedia.co.uk/Ashuwillticook-Rail-Trail.d811531152953708544.Holidays-City-Breaks) - [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) ![](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. Scan the QR code with your device camera and download our app