Title: Chester Travel Guide: Best of Chester, Massachusetts Travel 2026 | Expedia.co.uk [Hotels in Chester](https://expedia.co.uk/Chester-Hotels.d6005399.Travel-Guide-Hotels)[Holiday Rentals in Chester](https://expedia.co.uk/Chester-Holiday-Rentals.d6005399.Travel-Guide-HolidayRentals)[Chester Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Chester.d6005399.Car-Hire-Guide)[Chester Holidays](https://expedia.co.uk/Chester.d6005399.Holidays-City-Breaks) # Chester Travel Guide ## Tourist 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 ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-uk-fr-de.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Holiday Sale Members save up to 40% on hotels and holiday homes. Plan this year’s big trip and save. [Book now](https://expedia.co.uk/cheap-deals?rfrr=DX_SPRING_PROMO_6005399) - Top hotels in Chester - Top Holiday 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 £110 28 Mar - 29 Mar includes taxes & fees 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 their reviews. Popular ... 9.2/10 Wonderful! (2,205 reviews) There were many good things about the stay however; our room was super close to the interstate and the traffic and trucks starting rolling by at 5:30 am. I searched for earplugs and it was not conducive to easy sleep. I would not stay again unless the room was far away from the highway. Be forewarned. ... Reviewed on 27 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=28%2F03%2F2026&endDate=29%2F03%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 £111 12 Mar - 13 Mar 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! (865 reviews) Overcharged and lied to said security deposit was released back but never was Reviewed on 26 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=12%2F03%2F2026&endDate=13%2F03%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 £77 9 Mar - 10 Mar includes taxes & fees Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ... 9.2/10 Wonderful! (1,001 reviews) Room is attractive and clean and the staff is always welcoming. Back rooms, where we stay, are quiet and look out across a marsh to the mountain. Reviewed on 28 Feb 2026 [](https://expedia.co.uk/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=54944&PinnedHotelID=54944&HadPinnedHotel=true®ionId=6005399) [See all 855 properties in Chester](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=01%2F03%2F2026&endDate=02%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/19000000/18110000/18110000/18109961/5c348ca4_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 ... 8.6/10 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 9 Feb 2026 [](https://expedia.co.uk/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 holiday home in Lanesborough. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ... 10/10 Exceptional! (12 reviews) The house had all we needed and we enjoyed the stay very much. Lots of room and amenities with soap, toothpaste, plenty of towels, plenty of kitchen utensils and spices. Great service too! Adam tested the bbq when we arrived and determined it wasn’t working so he brought us a new one an hour later! ... Reviewed on 22 Feb 2026 [](https://expedia.co.uk/Lanesborough-Hotels-Cozy-Lake-House-With-Hot-Tub-Enjoy-Everything-The-Berkshires-Have-To-Offer.h95207502.Hotel-Information) ![Peace and quiet on the lake](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/afd0b229_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Peace and quiet on the lake Becket MA Stay at this holiday home in Becket. Enjoy free Wi-Fi, 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 18 Feb 2026 [](https://expedia.co.uk/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information) [See all properties in Chester](https://expedia.co.uk/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.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-02-28&endDate=2026-03-01)[28 Feb - 1 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-02-28&endDate=2026-03-01) [Tomorrow night ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-03-01&endDate=2026-02-02)[1 Mar - 2 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=2026-03-01&endDate=2026-02-02) [Next weekend ](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=06%2F03%2F2026&endDate=08%2F03%2F2026)[6 Mar - 8 Mar](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=6005399&startDate=06%2F03%2F2026&endDate=08%2F03%2F2026) ### Popular places to visit #### Chester Town Hall You can get tickets for a performance at Chester Town Hall on your trip to Chester. Wander the lakeside and forests in this relaxing area. [](https://expedia.co.uk/Chester-Town-Hall-Chester.d553248621532666604.Attraction) ## Cities near Chester ![Dynamite Box Trail ](https://images.trvl-media.com/place/80625/a3f7996f-c96b-4ae3-a3b7-bd1e78dfeca4.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Blandford ![autumn at Becket Quarry in Massachusetts](https://images.trvl-media.com/place/6005395/c64599a0-954b-430e-84bf-e6469837fde4.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Becket - Cities near Chester - Places of interest [Blandford](https://expedia.co.uk/Blandford.dx80625)[Becket](https://expedia.co.uk/Becket.dx6005395) - [Tanglewood Music Center ](https://expedia.co.uk/Tanglewood-Music-Center-Lenox.d503292.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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