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 ![Chester](https://images.trvl-media.com/place/6005399/400cb5cc-e1d2-4765-9a2f-8870b6e8f711.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Chester](https://images.trvl-media.com/place/6005399/e07d81b9-4cfd-44e9-aa03-54ce0d82eb8f.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Chester](https://images.trvl-media.com/place/6005399/91212232-e0eb-41d1-adb5-d561fb8ac42c.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Chester](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Chester](https://images.trvl-media.com/place/6005399/0c1b1cf1-f718-45ae-a4ad-16ba5e76c8dc.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/1000000/850000/849400/849303/8974a65a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### D. Hotel Suites & Spa 1 Country Club Rd Holyoke MA CA $170 CA $198 total Apr 14 - Apr 15 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. ... 9.4/10 Exceptional! (2,224 reviews) Staff was amazing! Rooms were spotless. Reviewed on Mar 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=14%2F04%2F2026&endDate=15%2F04%2F2026&selected=849303&PinnedHotelID=849303&HadPinnedHotel=true®ionId=6005399) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshire Mountain Lodge 8 Dan Fox Dr Pittsfield MA Fully refundable CA $120 CA $165 total Apr 26 - Apr 27 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! (888 reviews) very clean and friendly staff Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F04%2F2026&endDate=27%2F04%2F2026&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=6005399) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Berkshires Untold 194 Pittsfield Rd Lenox MA CA $96 CA $108 total Mar 31 - Apr 1 includes taxes & fees Stay at this lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ... 9/10 Wonderful! (881 reviews) Berkshires Untold is an old roadside motel that has been very spiffed up. The rooms are small but clean, comfortable, and nicely decorated and updated. Our bed was comfy with high end linens and a nice updated bathroom. The major drawback to the room is the very noisy HVAC unit. There's a super cozy, ... Reviewed on Mar 26, 2026 [](https://expedia.ca/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=76297618&PinnedHotelID=76297618&HadPinnedHotel=true®ionId=6005399) [See all 876 properties in Chester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=28%2F03%2F2026&endDate=29%2F03%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/eda478dd_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 Tanglewood Music Center and The Mount are located ... 8.6/10 Excellent! (141 reviews) I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ... Reviewed on Feb 9, 2026 [](https://expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information) ![Peace and quiet on the lake](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/2959f9e4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Peace and quiet on the lake Becket MA Stay at this vacation home in Becket. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ... 9.6/10 Exceptional! (234 reviews) Host was great! Quick communication. Place is a gem for peace and tranquility! The home is beautiful with great view. Reviewed on Feb 18, 2026 [](https://expedia.ca/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information) ![Family Ski Getaway in the Berkshires](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Family Ski Getaway in the Berkshires Great Barrington MA Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Monument Mountain Reservation and Art ... 9/10 Wonderful! (12 reviews) Loved our time here. It was a very cozy set up for a snowy week away, with a pellet stove, an ample amount of puzzles stocked in the house, and the surprise perk of Studley, a 12 year old cuddle machine of a cat who lives here and provided great company. The host was very responsive to all of my ... Reviewed on Mar 4, 2026 [](https://expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.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=2026-03-27&endDate=2026-03-28)[Mar 27 - Mar 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-03-27&endDate=2026-03-28) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-03-28&endDate=2026-03-29)[Mar 28 - Mar 29](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-03-28&endDate=2026-03-29) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=27%2F03%2F2026&endDate=29%2F03%2F2026)[Mar 27 - Mar 29](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=27%2F03%2F2026&endDate=29%2F03%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) - [Norman Rockwell Museum ](https://expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction) - [Big E ](https://expedia.ca/Big-E-West-Springfield.d553248621533116953.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) - [Don Muller Gallery ](https://expedia.ca/Don-Muller-Gallery-Northampton.d553248621532666664.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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