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 ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/af3c140d-6448-4a00-9ca4-43cb22b4b44b.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/86318a94-cc98-4d4a-a83c-e012ece6ff66.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![An autumn view of Cheshire Lake in the Berkshire Mountains of Western Massachusetts.](https://images.trvl-media.com/place/6005398/81bbd72e-e9b3-4d05-ac68-b2406c65563e.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..](https://images.trvl-media.com/place/6005398/5524f182-4aec-4e46-bab1-4eb1dd804bd0.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## 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 £93 10 Feb - 11 Feb 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! (2,227 reviews) Spacious 2 bed 2 bath! Reviewed on 3 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=6005398) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA £97 10 Feb - 11 Feb includes taxes & fees Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ... 9/10 Wonderful! (827 reviews) Room was clean and nicely equipped with kitchen. Will return if the future. Reviewed on 1 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=10%2F02%2F2026&endDate=11%2F02%2F2026&selected=11449113&PinnedHotelID=11449113&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 £150 11 Mar - 12 Mar 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! (572 reviews) Clean Reviewed on 31 Jan 2026 [](https://expedia.co.uk/Hotel-Search?startDate=11%2F03%2F2026&endDate=12%2F03%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true®ionId=6005398) [See all 1,004 properties in Cheshire](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=10%2F02%2F2026&endDate=11%2F02%2F2026®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! (2,227 reviews) Spacious 2 bed 2 bath! Reviewed on 3 Feb 2026 [](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 ... 9.2/10 Wonderful! (8 reviews) Healthy food too! Reviewed on 20 Oct 2025 [](https://expedia.co.uk/Williamstown-Hotels-Huttopia-Berkshires.h113777287.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 ski condo in Hancock. Enjoy free parking, 2 restaurants and 2 hot tubs. Our guests praise the property condition in their reviews. Popular attractions ... 8.2/10 Very Good! (989 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) [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=2026-02-09&endDate=2026-02-10)[9 Feb - 10 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2026-02-09&endDate=2026-02-10) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2026-02-10&endDate=2026-02-11)[10 Feb - 11 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2026-02-10&endDate=2026-02-11) [This weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[13 Feb - 15 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026)[20 Feb - 22 Feb](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=20%2F02%2F2026&endDate=22%2F02%2F2026) ### 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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[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) - [Williams College ](https://expedia.co.uk/Williams-College-Williamstown.d6091833.Attraction) - [Green Mountain National Forest ](https://expedia.co.uk/Green-Mountain-National-Forest-Vermont.d6115904.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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