Title: Unique Hotels in Chester 2026 | Expedia.co.uk [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) ![An amazing keystone arch bridge!](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams ![](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Chester Pool [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=POOL) Apart­ment [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=APARTMENT) Pet friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=PETS) Family friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&travelerType=family_friendly) Hot tub [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&amenities=HOT_TUB) Condo [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=CONDO) Cottage [](https://www.expedia.co.uk/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-03-12&d1=2026-03-12&endDate=2026-03-14&d2=2026-03-14&lodging=COTTAGE) ## Check prices for these dates Tonight [26 Feb - 27 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6005399&startDate=2026-02-26&endDate=2026-02-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [27 Feb - 28 Feb](https://www.expedia.co.uk/Hotel-Search?regionId=6005399&startDate=2026-02-27&endDate=2026-02-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [27 Feb - 1 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6005399&startDate=2026-02-27&endDate=2026-03-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [6 Mar - 8 Mar](https://www.expedia.co.uk/Hotel-Search?regionId=6005399&startDate=2026-03-06&endDate=2026-03-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels ![Standard Room, 2 Queen Beds, Non Smoking | Pillow-top beds, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-3661e0ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Kitchen (with Sofabed, Full Kitchen) | Private kitchenette | Microwave](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5753h3840x5y0-8e399dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Kitchen (Larger Room, Sofabed, Full Kitchen) | Pillow-top beds, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/b5bac949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-c074381d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baldwin Inn & Suites, SureStay Collection by Best Western [](https://www.expedia.co.uk/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) West Springfield 7.8/10 Good (119 reviews) "Clean room and very spacious, staff was friendly, i would only add a small dinning table to the room. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tomarie £74 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/44ab9667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel [](https://www.expedia.co.uk/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) Great Barrington 9.0/10 Wonderful (824 reviews) "The room was clean, and the staff was friendly and helpful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Damien [](https://www.expedia.co.uk/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom | Premium bedding, down duvets, pillow-top beds, individually furnished](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/3908437c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires [](https://www.expedia.co.uk/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.6/10 Exceptional (20 reviews) "Spotless rooms and the friendliest service at the front desk! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary £115 includes taxes & fees 12 Mar - 13 Mar [](https://www.expedia.co.uk/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/83c805e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites [](https://www.expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) Pittsfield 8.6/10 Excellent (1,005 reviews) "Very friendly and good Breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse £79 includes taxes & fees 12 Mar - 13 Mar [](https://www.expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/efe975c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite | Premium bedding, individually decorated, individually furnished, desk](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/12b5137a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/cab085ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### D. Hotel Suites & Spa [](https://www.expedia.co.uk/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) Holyoke 9.4/10 Exceptional (2,238 reviews) "Great service, clean & quiet rooms, and a solid breakfast to start the day" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie £110 includes taxes & fees 28 Mar - 29 Mar [](https://www.expedia.co.uk/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/a50fdd34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Studio, 1 King Bed | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/b8e5643f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, Multiple Beds | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/9704ee61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, Multiple Beds | Desk, laptop workspace, free WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/1eae2c98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Valley Inn [](https://www.expedia.co.uk/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information) West Hatfield 8.4/10 Very good (112 reviews) "Friendly staff, really nice room, quiet. I really enjoyed my stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Desiree £82 includes taxes & fees 5 Mar - 6 Mar [](https://www.expedia.co.uk/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/2558ee66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/bb325877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/390a52f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pleasant Valley Motel West Stockbridge [](https://www.expedia.co.uk/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) West Stockbridge 6.8/10 (1,001 reviews) "Priced very reasonably and the room was clean and comfy!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne £47 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/2a79c048.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/5b7eab2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/c682c6c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/16000000/15920000/15914400/15914307/4592453d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites Springfield Holyoke [](https://www.expedia.co.uk/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information) Holyoke 9.2/10 Wonderful (614 reviews) "Room was spotless, staff were nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jose I Medina £97 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-Holyoke.h15914307.Hotel-Information) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/17f29286.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox [](https://www.expedia.co.uk/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) Lenox 7.6/10 Good (834 reviews) "Clean room and the bed was very comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arlan £57 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/775c3761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/w1020h764x4y4-6e21e3db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/04be04d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue – A Modern Hotel, an Ascend Collection Hotel [](https://www.expedia.co.uk/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information) West Springfield 9.4/10 Exceptional (150 reviews) "Exceptionally clean, loved the massage chair and free shampoo .. the beds were so comfy!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jackie £100 includes taxes & fees 22 Mar - 23 Mar [](https://www.expedia.co.uk/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/b9956cb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down duvets, blackout curtains, iron/ironing board](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/f36d24b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/08190a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/40e8ece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Chicopee Springfield [](https://www.expedia.co.uk/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) Chicopee 9.0/10 Wonderful (1,000 reviews) "Friendly clean accommodation were just what we needed. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carrie £89 includes taxes & fees 16 Mar - 17 Mar [](https://www.expedia.co.uk/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/6a569eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold [](https://www.expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) Lenox 9.0/10 Wonderful (864 reviews) "This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa [](https://www.expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/14200/14144/a76d0174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/1000000/20000/14200/14144/2f3875b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/20000/14200/14144/e4ed4dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/20000/14200/14144/6ac05c63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Springfield West Inn [](https://www.expedia.co.uk/Springfield-Hotels-Best-Western-Springfield-West-Inn.h14144.Hotel-Information) West Springfield 7.8/10 Good (1,001 reviews) "The room was great and jose at the front desk was very kind amd helpful and at the breakfast department he was great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) LUIS £74 includes taxes & fees 1 Mar - 2 Mar [](https://www.expedia.co.uk/Springfield-Hotels-Best-Western-Springfield-West-Inn.h14144.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3f4a1adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1,000 reviews) "Very friendly staff comfy beds!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giselle £76 includes taxes & fees 12 Mar - 13 Mar [](https://www.expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast ](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/0f74ae3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/47150b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking | Desk, iron/ironing board, cots/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Lee - Lenox South [](https://www.expedia.co.uk/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) Lee 8.4/10 Very good (1,000 reviews) "Safe, clean rooms, decent breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Neil £71 includes taxes & fees 26 Mar - 27 Mar [](https://www.expedia.co.uk/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![In-room safe, desk, free cots/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Non Smoking | In-room safe, desk, free cots/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking | In-room safe, desk, free cots/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires [](https://www.expedia.co.uk/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) Great Barrington 7.6/10 Good (572 reviews) "Excellent location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul Samad £62 includes taxes & fees 12 Mar - 13 Mar [](https://www.expedia.co.uk/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b138d836.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Accessible | Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/644deeee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic Area](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/de2ab5d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b4275c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Inn [](https://www.expedia.co.uk/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) Pittsfield 7.8/10 Good (844 reviews) "This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARIA J £69 includes taxes & fees 2 Mar - 3 Mar [](https://www.expedia.co.uk/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.0/10 Wonderful (1,000 reviews) "Clean room, nice staff , decent breakfast. Overall a good stay . " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anindita £81 includes taxes & fees 18 Mar - 19 Mar [](https://www.expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Free daily full breakfast ](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/919a842d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/aa01ab9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/8cf443f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mort's Library | Individually decorated, individually furnished, iron/ironing board](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/f25262f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Naomi's Inn Bed & Breakfast [](https://www.expedia.co.uk/Springfield-Hotels-Naomis-Inn-Bed-Breakfast.h1673139.Hotel-Information) Liberty Heights 9.0/10 Wonderful (427 reviews) "Artful and inspiring interior decorating and delicious French toast for breakfast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marielle £85 includes taxes & fees 15 Mar - 16 Mar [](https://www.expedia.co.uk/Springfield-Hotels-Naomis-Inn-Bed-Breakfast.h1673139.Hotel-Information) ![Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/22135a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Double Room, 2 Queen Beds, Courtyard View | Premium bedding, pillow-top beds, in-room safe, blackout curtains](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/3d6dcf9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/b642a3ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn [](https://www.expedia.co.uk/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) Great Barrington 9.6/10 Exceptional (38 reviews) "The room was clean and comfortable wi will back next year:) " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nadya £103 includes taxes & fees 20 Mar - 21 Mar [](https://www.expedia.co.uk/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) 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. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2026-03-12&endDate=2026-03-13®ionId=6005399&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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=HTG_SPRING_PROMO_6005399) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d6005399.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d6005399.Travel-Guide-Hotels) ## Stay near popular Chester attractions ### 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. [See properties](https://www.expedia.co.uk/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532666604) ## Learn more about Chester Experience the hiking, camping and waterfalls in Chester! [See all hotels in Chester](https://www.expedia.co.uk/Hotel-Search?startDate=2026-03-12&endDate=2026-03-13&adults=2®ionId=6005399) ![An amazing keystone arch bridge!](https://images.trvl-media.com/place/6005399/89add9e6-2382-4d4a-a865-76e87fb66a41.jpg?impolicy=fcrop&w=473&h=473&p=1&q=high) Photo by Chris Addams ## Top Chester Hotel Reviews ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Nice and responsive" [](https://expedia.co.uk/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 10/10 Excellent "Very spacious and comfortable. Great for families." [](https://expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Clean room nice staff" [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "Affordable price, clean bedroom and close to everything. " [](https://expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "Amazing first time experience! Super friendly staff f from check in to check out! Exceptionally clean and cozy! " [](https://expedia.co.uk/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Fairfield Inn & Suites Springfield Northampton/Amherst](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/e6abed3c_y.jpg) ### Fairfield Inn & Suites Springfield Northampton/Amherst 10/10 Excellent "Very nice room and nice people!" [](https://expedia.co.uk/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-NorthamptonAmherst.h8449737.Hotel-Information) ![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21_y.jpg) ### Tru by Hilton Chicopee Springfield 10/10 Excellent "Staff was fab" [](https://expedia.co.uk/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Room was clean and suite was huge, staff was friendly and helpful, pool and game room were great for my kids. All was great for a Feb vacation getaway! " [](https://expedia.co.uk/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Blue – A Modern Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2_y.jpg) ### Blue – A Modern Hotel, an Ascend Collection Hotel 10/10 Excellent "The staff was courteous, the room was very clean, but the massage chair was the best." [](https://expedia.co.uk/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information) ## More cheap stays in Chester ![Riverdale Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459711/28e65efc_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Riverdale Inn 1500 Riverdale Street West Springfield MA £58 2 Mar - 3 Mar includes taxes & fees 5.8/10 (999 reviews) [](https://expedia.co.uk/Springfield-Hotels-Super-8-By-Wyndham-West-SpringfieldRoute-5.h459711.Hotel-Information) ![Quality Inn West Springfield](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/7f7ace74_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn West Springfield 1150 Riverdale St West Springfield MA £67 12 Mar - 13 Mar includes taxes & fees 7/10 Good! (1,007 reviews) [](https://expedia.co.uk/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn 170 Housatonic Street Lee MA £71 26 Mar - 27 Mar includes taxes & fees 8.4/10 Very Good! (1,000 reviews) [](https://expedia.co.uk/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![Red Roof Inn PLUS+ West Springfield](https://images.trvl-media.com/lodging/1000000/30000/27100/27090/23b7c14f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Red Roof Inn PLUS+ West Springfield 1254 Riverdale Street West Springfield MA £71 1 Mar - 2 Mar includes taxes & fees 6.8/10 (1,000 reviews) [](https://expedia.co.uk/Springfield-Hotels-Red-Roof-Inn-PLUS-West-Springfield.h27090.Hotel-Information) ![Quality Inn & Suites Northampton - Amherst](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/f86e1269_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn & Suites Northampton - Amherst 117 Conz St Northampton MA £83 5 Mar - 6 Mar includes taxes & fees 7.2/10 Good! (1,000 reviews) [](https://expedia.co.uk/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information) ![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Tru by Hilton Chicopee Springfield 440 Memorial Dr Chicopee MA £89 16 Mar - 17 Mar includes taxes & fees 9/10 Wonderful! (1,000 reviews) [](https://expedia.co.uk/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ## Hotels in Chester with star rating ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 11 properties [](https://expedia.co.uk/4Star-Chester-Hotels.s40-0-d6005399.Travel-Guide-Filter-Hotels) ## Frequently asked questions ### What is the best area to stay in Chester? > This area is the heart of Chester, offering a pleasant and quiet New England village experience. You'll find charming historic buildings, local shops, and eateries concentrated around the town green. The Westfield River runs nearby, adding to the scenic appeal. > > > Couples looking for a relaxing getaway will appreciate this area. It provides easy access to local hiking trails, such as those in the Chester-Blandford State Forest, and opportunities for scenic drives through the Berkshire foothills. The calm atmosphere is superb for unwinding. ### When is the best time to go to Chester? > During these months, the average daily temperatures range from 20°C to 28°C, making it ideal for exploring the natural beauty of the area, including the many hiking trails and the Chester-Blandford State Forest. The warm weather also allows for comfortable enjoyment of the town's small shops and eateries. > > > Couples looking for a relaxing escape will find these months particularly appealing. The pleasant weather provides great conditions for scenic drives through the Berkshire Hills, picnics by the Westfield River, or simply unwinding on a porch with views of the lush greenery. Many local accommodations also offer outdoor amenities that are best enjoyed in the summer. > > > For those interested in local events, late summer often brings community gatherings and farmers' markets, adding a touch of local flavour to your visit. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Chester hotel booking with Expedia? ### How much is the nightly rate at a Chester hotel? ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - More ways to book - [3 Star Hotels in The Berkshires ](https://www.expedia.co.uk/3Star-The-Berkshires-Hotels.s30-0-d6047665.Travel-Guide-Filter-Hotels) - [4 Star Hotels in The Berkshires ](https://www.expedia.co.uk/4Star-The-Berkshires-Hotels.s40-0-d6047665.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Western Massachusetts ](https://www.expedia.co.uk/4Star-Western-Massachusetts-Hotels.s40-0-d6234063.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Worthington ](https://www.expedia.co.uk/5Star-Worthington-Hotels.s50-0-d6005428.Travel-Guide-Filter-Hotels) - 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