Title: Visit Chester: Best of Chester Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Vacation Rentals in Chester](https://expedia.ca/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals)[Chester Car Rentals](https://expedia.ca/Car-Rentals-In-Chester.d6005399.Car-Rental-Guide)[Chester Vacation Packages](https://expedia.ca/Chester.d6005399.Destination-Travel-Guides) # Chester ## Travel Guide ![Frozen Sanderson Brook Falls in Chester ](https://images.trvl-media.com/place/6005399/400cb5cc-e1d2-4765-9a2f-8870b6e8f711.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Frozen Sanderson Brook Falls in Chester ](https://images.trvl-media.com/place/6005399/400cb5cc-e1d2-4765-9a2f-8870b6e8f711.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Newman Marsh Trail near Mica Mine trail ](https://images.trvl-media.com/place/6005399/e07d81b9-4cfd-44e9-aa03-54ce0d82eb8f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Some beautiful cascades pouring into the Westfield River. ](https://images.trvl-media.com/place/6005399/91212232-e0eb-41d1-adb5-d561fb8ac42c.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![An amazing keystone arch bridge!](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Chester Things to do - Chester Hotel Deals - Vacation Rentals in Chester ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### D. Hotel Suites & Spa 1 Country Club Rd Holyoke MA CA $141 CA $164 total Feb 8 - Feb 9 includes taxes & fees Book a stay at this spa hotel in Holyoke. Enjoy a full-service spa, 2 restaurants, and room service. Our guests praise the breakfast and the pool in our reviews. ... 9.2/10 Wonderful! (2,238 reviews) Clean, safe, quiet, and comfortable. Fantastic full breakfast as always. Reviewed on Feb 6, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=849303&PinnedHotelID=849303&HadPinnedHotel=true®ionId=6005399) ![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 CA $135 CA $181 total Feb 8 - Feb 9 includes taxes & 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! (825 reviews) We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being ... Reviewed on Feb 1, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=6005399) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Yankee, Trademark Collection by Wyndham 461 Pittsfield Rd Lenox MA CA $134 CA $150 total Feb 8 - Feb 9 includes taxes & fees Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ... 9/10 Wonderful! (1,010 reviews) The staff is very helpful, and always willing to assist with any inquiries. The room was definitely clean and well-stocked throughout our entire stay. Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F02%2F2026&endDate=09%2F02%2F2026&selected=54944&PinnedHotelID=54944&HadPinnedHotel=true®ionId=6005399) [See all 849 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=6005399) 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. ![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.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information) ![Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!](https://images.trvl-media.com/lodging/96000000/95210000/95207600/95207502/fb316035_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer! Lanesborough MA Stay at this vacation home in Lanesborough. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ... 10/10 Exceptional! (10 reviews) Perfect spot to get in a few days of skiing at Jiminy. Well stocked with the basics and hot tub was great. Very responsive host. Reviewed on Jan 18, 2026 [](https://expedia.ca/Lanesborough-Hotels-Cozy-Lake-House-With-Hot-Tub-Enjoy-Everything-The-Berkshires-Have-To-Offer.h95207502.Hotel-Information) ![The Kemble- Built by a US Secretary of State in Lenox](https://images.trvl-media.com/lodging/77000000/76010000/76003400/76003386/5bf808fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Kemble- Built by a US Secretary of State in Lenox Lenox MA Book a stay at this family-friendly villa in Lenox. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Ventfort Hall Mansion and Gilded ... 9.8/10 Exceptional! (18 reviews) We stayed at The Kemble, the historic Lenox estate built by a U.S. Secretary of State, for a large family reunion with 10 adults and 16 children—and it was, without question, the best large-house experience we’ve ever had.We rent a large home every year, and nothing has come close to this. The house ... Reviewed on Jan 13, 2026 [](https://expedia.ca/Lenox-Hotels-The-Kemble-Built-By-A-US-Secretary-Of-State-In-Lenox.h76003386.Hotel-Information) [See all properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=6005399&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 Chester hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-02-07&endDate=2026-02-08)[Feb 7 - Feb 8](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-02-07&endDate=2026-02-08) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-02-08&endDate=2026-02-09)[Feb 8 - Feb 9](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-02-08&endDate=2026-02-09) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[Feb 13 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) ### Popular places to visit #### Chester Town Hall You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area. [](https://expedia.ca/Chester-Town-Hall-Chester.d553248621532666604.Vacation-Attraction) - Cities near Chester - Places of interest - [National Shrine of the Divine Mercy ](https://expedia.ca/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction) - [Big E ](https://expedia.ca/Big-E-West-Springfield.d553248621533116953.Vacation-Attraction) - [Norman Rockwell Museum ](https://expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction) - [Eastern States Exposition ](https://expedia.ca/Eastern-States-Exposition-West-Springfield.d6070273.Vacation-Attraction) - [Naumkeag Museum ](https://expedia.ca/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction) - [Ventfort Hall Mansion and Gilded Age Museum ](https://expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction) - [Lenox Library ](https://expedia.ca/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on 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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