Title: Visit Cheshire: 2026 Travel Guide for Cheshire, Massachusetts | Expedia.com [Hotels in Cheshire](https://expedia.com/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.com/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.com/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[Car Rentals in Cheshire](https://expedia.com/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.com/Cheshire.d6005398.Destination-Travel-Guides) # Cheshire, MA ## Travel 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 - Cheshire Hotel Deals - Vacation 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 $126 nightly $141 total Feb 22 - Feb 23 Total with taxes and fees Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ... 8.6/10 Excellent! (2,227 reviews) Spacious 2 bed 2 bath! Reviewed on Feb 3, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F22%2F2026&endDate=2%2F23%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 $121 nightly $136 total Mar 8 - Mar 9 Total with taxes and fees Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ... 9/10 Wonderful! (826 reviews) Room was clean and nicely equipped with kitchen. Will return if the future. Reviewed on Feb 1, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F8%2F2026&endDate=3%2F9%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 $208 nightly $233 total Mar 1 - Mar 2 Total with taxes and fees Book a stay at this business-friendly hotel in Williamstown. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our ... 9.6/10 Exceptional! (572 reviews) Clean Reviewed on Jan 31, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=35658765&PinnedHotelID=35658765&HadPinnedHotel=true®ionId=6005398) [See all 1,006 properties in Cheshire](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=2%2F8%2F2026&endDate=2%2F9%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 Book a stay at this family-friendly condo in Williamstown. Enjoy free parking, a fitness center, and a 24-hour front desk. Our guests praise the helpful staff ... 8.6/10 Excellent! (2,227 reviews) Spacious 2 bed 2 bath! Reviewed on Feb 3, 2026 [](https://expedia.com/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 campground 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 Oct 20, 2025 [](https://expedia.com/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 WiFi, free parking, and a fitness center. Popular attractions The Mount and Wyndhurst Golf & Club are located ... 8.4/10 Very Good! (140 reviews) Condo was a great space. Bathroom walls should be repainted as stains are evident. There were also stains on the couch which I cleaned. Reviewed on Jan 3, 2026 [](https://expedia.com/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information) [See all properties in Cheshire](https://expedia.com/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.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2026-02-07&endDate=2026-02-08)[Feb 7 - Feb 8](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2026-02-07&endDate=2026-02-08) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2026-02-08&endDate=2026-02-09)[Feb 8 - Feb 9](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2026-02-08&endDate=2026-02-09) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026)[Feb 13 - Feb 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005398&startDate=2%2F13%2F2026&endDate=2%2F15%2F2026) ### Popular places to visit #### St Mary's of the Assumption Church 5/5(1 review) 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.com/St-Marys-Of-The-Assumption-Church-Cheshire.d553248621532665539.Vacation-Attraction) ## Cities near Cheshire ![Wahconah Falls in the Berkshires](https://images.trvl-media.com/place/6911/0d61b065-dfb2-41c6-8d5b-cded88165403.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Dalton ![Deer Hill Shelter is a backpackers shelter, and therefore FREE, unlike the other camp areas on Mt Greylock. It's only about a mile and half from the parking area nearest to Campground Trail. Deer Hill Trail itself branches off from Campground Trail to take you to the shelter. Map location is approximate since it doesn't show all the trails and the shelter is dwarfed by the surrounding forest. First come, first serve here ... and if you show up in the middle of the week in early summer, you might get it all to yourself like we did!](https://images.trvl-media.com/place/183333/ba4e7fc4-6985-4957-b20c-a1c15dc92f0e.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### New Ashford ![Main Street USA, North Adams, Massachusetts](https://images.trvl-media.com/place/6005393/cc755750-f4dd-4b43-9817-f53d7ef5c03c.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Adams ![WW2 Vetrans War Memorial Veterans War Memorial located in Lanesborough, MA The summit of Mt. Greylock](https://images.trvl-media.com/place/6005408/e6fe22ae-eb57-4b13-a5fa-fe1cb4a88ae8.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Lanesborough ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near St Mary's of the Assumption Church ](https://www.expedia.com/St-Marys-Of-The-Assumption-Church-Hotels.0-l553248621532665539-0.Travel-Guide-Filter-Hotels) - [Hotels near Mount Greylock State Reservation Visitor Center ](https://www.expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Hotels.0-l6272782-0.Travel-Guide-Filter-Hotels) - [Lanesborough Hotels ](https://www.expedia.com/Lanesborough-Hotels.d6005408.Travel-Guide-Hotels) - [B&B in Lanesborough ](https://www.expedia.com/Lanesborough-Bed-And-Breakfast.d6005408-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Lanesborough ](https://www.expedia.com/Lanesborough-Hotels-Cheap-Hotels.0-0-d6005408-tCheapHotels.Travel-Guide-Filter-Hotels) - [Apartments in Lanesborough ](https://www.expedia.com/Lanesborough-Apartments.d6005408-aaApartments.Travel-Guide-Accommodation) - [Cottages in Lanesborough ](https://www.expedia.com/Lanesborough-Cottages.d6005408-aaCottages.Travel-Guide-Accommodation) - [Luxury Hotels in Lanesborough ](https://www.expedia.com/Lanesborough-Hotels-Luxury-Hotel.0-0-d6005408-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Cabin Rentals in Lanesborough ](https://www.expedia.com/Lanesborough-Cabins.d6005408-aaCabins.Travel-Guide-Accommodation) - [Resorts in Lanesborough ](https://www.expedia.com/Lanesborough-Resorts.d6005408-aaResorts.Travel-Guide-Accommodation) - [Motels in Lanesborough ](https://www.expedia.com/Lanesborough-Motels.d6005408-aaMotels.Travel-Guide-Accommodation) - [Aparthotels in Lanesborough ](https://www.expedia.com/Lanesborough-Apart-Hotels.d6005408-aaApartHotels.Travel-Guide-Accommodation) - [Condo Rentals in Lanesborough ](https://www.expedia.com/Lanesborough-Condos.d6005408-aaCondos.Travel-Guide-Accommodation) - [Vacation Homes in Lanesborough ](https://www.expedia.com/Lanesborough-Private-Vacation-Homes.d6005408-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Ski Hotels in Lanesborough ](https://www.expedia.com/Lanesborough-Hotels-Ski-Hotel.0-0-d6005408-tSkiHotel.Travel-Guide-Filter-Hotels) - [Hotels near Susan B. 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[Hotels near Mount Greylock ](https://www.expedia.com/Mount-Greylock-Hotels.0-l6091829-0.Travel-Guide-Filter-Hotels) - [Hotels near Skyline Country Club ](https://www.expedia.com/Skyline-Country-Club-Hotels.0-l553248621532665295-0.Travel-Guide-Filter-Hotels) - [Hotels near Wahconah Falls State Park ](https://www.expedia.com/Wahconah-Falls-State-Park-Hotels.0-l553248621532665297-0.Travel-Guide-Filter-Hotels) - [Dalton Hotels ](https://www.expedia.com/Dalton-Hotels.d6911.Travel-Guide-Hotels) - [Hancock Hotels ](https://www.expedia.com/Hancock-Hotels.d112303.Travel-Guide-Hotels) - [Cabin Rentals in Dalton ](https://www.expedia.com/Dalton-Cabins.d6911-aaCabins.Travel-Guide-Accommodation) - [B&B in Dalton ](https://www.expedia.com/Dalton-Bed-And-Breakfast.d6911-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Dalton ](https://www.expedia.com/Dalton-Condos.d6911-aaCondos.Travel-Guide-Accommodation) - [Resorts in Dalton ](https://www.expedia.com/Dalton-Resorts.d6911-aaResorts.Travel-Guide-Accommodation) - [Motels in Dalton ](https://www.expedia.com/Dalton-Motels.d6911-aaMotels.Travel-Guide-Accommodation) - [Condo Rentals in Hancock ](https://www.expedia.com/Hancock-Condos.d112303-aaCondos.Travel-Guide-Accommodation) - [Resorts & Hotels with Spas in Hancock ](https://www.expedia.com/Hancock-Hotels-Spa-Hotel.0-0-d112303-tSpaHotel.Travel-Guide-Filter-Hotels) - [Resorts in Hancock ](https://www.expedia.com/Hancock-Resorts.d112303-aaResorts.Travel-Guide-Accommodation) - [Hotels with Restaurants in Hancock ](https://www.expedia.com/Hancock-Hotels-Hotels-With-Restaurants.0-0-d112303-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Hancock ](https://www.expedia.com/Hancock-Hotels-Luxury-Hotel.0-0-d112303-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Hancock ](https://www.expedia.com/3Star-Hancock-Hotels.s30-0-d112303.Travel-Guide-Filter-Hotels) - [Ski Hotels in Hancock ](https://www.expedia.com/Hancock-Hotels-Ski-Hotel.0-0-d112303-tSkiHotel.Travel-Guide-Filter-Hotels) - 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[Hotels with Bars in Hancock ](https://www.expedia.com/Hancock-Hotels-Bar-Hotel.0-0-d112303-tBarHotel.Travel-Guide-Filter-Hotels) - [Hotels with an Outdoor Pool in Hancock ](https://www.expedia.com/Hancock-Hotels-Hotels-With-Outdoor-Pool.0-0-d112303-tHotelswithOutdoorPool.Travel-Guide-Filter-Hotels) - [Hotels with a Gym in Hancock ](https://www.expedia.com/Hancock-Hotels-Hotels-With-Fitness-Center.0-0-d112303-tHotelswithFitnessCenter.Travel-Guide-Filter-Hotels) - [Historic Hotels in Hancock ](https://www.expedia.com/Hancock-Hotels-Historic-Hotel.0-0-d112303-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Family Hotels in Hancock ](https://www.expedia.com/Hancock-Hotels-Family-Hotel.0-0-d112303-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Golf Hotels in Hancock ](https://www.expedia.com/Hancock-Hotels-Golf-Hotel.0-0-d112303-tGolfHotel.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Hancock ](https://www.expedia.com/Hancock-Hotels-Hotels-With-Tennis-Courts.0-0-d112303-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Flights to Lanesborough ](https://www.expedia.com/Cheap-Flights-To-Lanesborough.d6005408.Travel-Guide-Flights) - [Flights from Lanesborough ](https://www.expedia.com/lp/flights/6005408/flights-from-lanesborough) - [Flights to Adams ](https://www.expedia.com/Cheap-Flights-To-Adams.d6005393.Travel-Guide-Flights) - [Flights from Adams ](https://www.expedia.com/lp/flights/6005393/flights-from-adams) - [Flights to Dalton ](https://www.expedia.com/Cheap-Flights-To-Dalton.d6911.Travel-Guide-Flights) - [Flights to Hancock ](https://www.expedia.com/Cheap-Flights-To-Hancock.d112303.Travel-Guide-Flights) - [Flights from Hancock ](https://www.expedia.com/lp/flights/112303/flights-from-hancock) - [Mount Greylock State Reservation Visitor Center ](https://www.expedia.com/Mount-Greylock-State-Reservation-Visitor-Center-Lanesborough.d6272782.Vacation-Attraction) - [Visit Lanesborough ](https://www.expedia.com/Lanesborough.dx6005408) - [Visit New Ashford ](https://www.expedia.com/New-Ashford.dx183333) - [Visit Adams ](https://www.expedia.com/Adams.dx6005393) - [Susan B. Anthony Birthplace Museum ](https://www.expedia.com/Susan-B-Anthony-Birthplace-Museum-Adams.d553248621532666696.Vacation-Attraction) - [East Hoosac Quaker Meetinghouse ](https://www.expedia.com/East-Hoosac-Quaker-Meetinghouse-Adams.d553248621561173644.Vacation-Attraction) - [Adams Vacations ](https://www.expedia.com/Adams.d6005393.Destination-Travel-Guides) - [Mount Greylock ](https://www.expedia.com/Mount-Greylock-Adams.d6091829.Vacation-Attraction) - [Visit Hancock ](https://www.expedia.com/Hancock.dx112303) - [Visit Dalton ](https://www.expedia.com/Dalton.dx6911) - [Wahconah Falls State Park ](https://www.expedia.com/Wahconah-Falls-State-Park-Dalton.d553248621532665297.Vacation-Attraction) - [Dalton Vacations ](https://www.expedia.com/Dalton.d6911.Destination-Travel-Guides) - [Hancock Vacations ](https://www.expedia.com/Hancock.d112303.Destination-Travel-Guides) - [Car rentals near Lanesborough ](https://www.expedia.com/Car-Rentals-In-Lanesborough.d6005408.Car-Rental-Guide) - [Car rentals near New Ashford ](https://www.expedia.com/Car-Rentals-In-New-Ashford.d183333.Car-Rental-Guide) - [Car rentals near Adams ](https://www.expedia.com/Car-Rentals-In-Adams.d6005393.Car-Rental-Guide) - [Car rentals near Dalton ](https://www.expedia.com/Car-Rentals-In-Dalton.d6911.Car-Rental-Guide) - [Car rentals near Hancock ](https://www.expedia.com/Car-Rentals-In-Hancock.d112303.Car-Rental-Guide) - [Lanesborough Vacation Rentals ](https://www.expedia.com/Lanesborough-Vacation-Rentals.d6005408.Travel-Guide-VacationRentals) - [Dalton Vacation Rentals ](https://www.expedia.com/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals) - [Hancock Vacation Rentals ](https://www.expedia.com/Hancock-Vacation-Rentals.d112303.Travel-Guide-VacationRentals) - Cities near Cheshire - Places of interest [Dalton](https://expedia.com/Dalton.dx6911)[New Ashford](https://expedia.com/New-Ashford.dx183333)[Adams](https://expedia.com/Adams.dx6005393)[Lanesborough](https://expedia.com/Lanesborough.dx6005408)[Savoy](https://expedia.com/Savoy.dx6005417)[Windsor](https://expedia.com/Windsor.dx6005427) - [Jiminy Peak Mountain Resort ](https://expedia.com/Jiminy-Peak-Mountain-Resort-Hancock.d553248621532665536.Vacation-Attraction) - 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