Title: Book The Best Hotels in Chester, MA for 2026 from CA $107 - Fully Refundable Options - Expedia.ca [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) ![This abandoned arch looms sixty-five feet over a beautiful oasis fed by small cascades. It's amazing sight to discover in autumn!](https://images.trvl-media.com/place/6005399/0c1b1cf1-f718-45ae-a4ad-16ba5e76c8dc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Chris Addams ![](https://images.trvl-media.com/place/6005399/0c1b1cf1-f718-45ae-a4ad-16ba5e76c8dc.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](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 Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-02-09&d1=2026-02-09&endDate=2026-02-11&d2=2026-02-11&travelerType=family_friendly) Pool [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-02-09&d1=2026-02-09&endDate=2026-02-11&d2=2026-02-11&amenities=POOL) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-02-09&d1=2026-02-09&endDate=2026-02-11&d2=2026-02-11&amenities=PETS) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-02-09&d1=2026-02-09&endDate=2026-02-11&d2=2026-02-11&amenities=HOT_TUB) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-02-09&d1=2026-02-09&endDate=2026-02-11&d2=2026-02-11&lodging=CABIN) Farm [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-02-09&d1=2026-02-09&endDate=2026-02-11&d2=2026-02-11&lodging=AGRITOURISM) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-02-09&d1=2026-02-09&endDate=2026-02-11&d2=2026-02-11&lodging=APARTMENT) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Chester%2C+Massachusetts%2C+United+States+of+America®ionId=6005399&latLong=42.279255%2C-72.978714&adults=2&startDate=2026-02-09&d1=2026-02-09&endDate=2026-02-11&d2=2026-02-11&lodging=COTTAGE) ## Check prices for these dates Tonight [Jan 26 - Jan 27](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-26&endDate=2026-01-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 27 - Jan 28](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-27&endDate=2026-01-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-30&endDate=2026-02-01&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels ![Room (Louis XIV)](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/9e954e9a.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) ![Porch](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/aa01ab9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Naomi's Inn Bed & Breakfast [](https://www.expedia.ca/Springfield-Hotels-Naomis-Inn-Bed-Breakfast.h1673139.Hotel-Information) Liberty Heights 9.0/10 Wonderful (424 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 CA $140 CA $159 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Springfield-Hotels-Naomis-Inn-Bed-Breakfast.h1673139.Hotel-Information) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/c7538df3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/19cf619f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/25529e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/b03b8d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pilgrim Inn [](https://www.expedia.ca/Lee-Hotels-Pilgrim-Inn.h49177721.Hotel-Information) Lee 5.8/10 (332 reviews) "Was horrible. Unsafe and scarey" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon CA $109 CA $122 total includes taxes & fees Feb 26 - Feb 27 [](https://www.expedia.ca/Lee-Hotels-Pilgrim-Inn.h49177721.Hotel-Information) ![In-room dining](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/ca66a901.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/017819f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/ec5f4855.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/fd5f12a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Lee - Great Barrington [](https://www.expedia.ca/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information) Lee 6.4/10 (655 reviews) "The room was clean and the service adequate" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $97 CA $108 total includes taxes & fees Feb 13 - Feb 14 [](https://www.expedia.ca/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/bb8fdf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/e112ee1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/3d2d74c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/08a849e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chambery Inn [](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) Lee 9.6/10 Exceptional (374 reviews) "Amazing customer service! Location was very good to explore the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sophia [](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) ![Suite, Private Bathroom (RedBird Suite) | View from room](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/a6ceeb05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool, open 9:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/5312662c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/w3000h1988x0y3-ae06d912.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Parlour Suite)](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/d4b17f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) Stockbridge 9.2/10 Wonderful (110 reviews) "Great breakfast, friendly helpful staff, pretty yard, good location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah CA $424 CA $513 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/bd64a090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/3ed5d9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c2037034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FairBridge Inn Express [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information) Pittsfield 5.4/10 (811 reviews) "Room spotless and staff helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $110 CA $123 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information) ![Standard Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/860000/856300/856259/7667da5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/856300/856259/5fdae7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/860000/856300/856259/2434fca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, desk, iron/ironing board, rollaway beds](https://images.trvl-media.com/lodging/1000000/860000/856300/856259/9dea6791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Chicopee - Springfield [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Chicopee-Springfield.h856259.Hotel-Information) Chicopee 6.4/10 (845 reviews) "Breakfast was convenient, loved coffee in the lobby and staff very friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julia CA $136 CA $154 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Chicopee-Springfield.h856259.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/219cd416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deep soaking bathtub](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/14870b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/6d051282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) Lee 7.6/10 Good (411 reviews) "Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $130 CA $145 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/8494e5b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #10 Queen's Cottage | Living room](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/e69747b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room #1 - Collins, 1 Queen Bed, Fireplace, not pet friendly](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/ae0cb55d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1580000/1575300/1575232/4f8b66e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Devonfield Inn B&B [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) Lee 10/10 Exceptional (134 reviews) "The inn has an excellent location and amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/7000000/6260000/6250400/6250331/6d969748.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/7000000/6260000/6250400/6250331/e44286b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/7000000/6260000/6250400/6250331/323c2406.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6260000/6250400/6250331/36e61773.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn Springfield Chicopee [](https://www.expedia.ca/Springfield-Hotels-Residence-Inn-Springfield-Chicopee.h6250331.Hotel-Information) Chicopee 9.2/10 Wonderful (481 reviews) "The hotel staff were very friendly and the hotel was clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samantha CA $197 CA $223 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Springfield-Hotels-Residence-Inn-Springfield-Chicopee.h6250331.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/91284a89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a97806ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) Pittsfield 8.0/10 Very good (1,002 reviews) "Staff was very courteous and rooms clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $134 CA $150 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/1f3ef87e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/3eac4fd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/88348850.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/b5bad44f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Stockbridge [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.Hotel-Information) Lee 9.8/10 Exceptional (99 reviews) "Well-run and elegant property. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $327 CA $384 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.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](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](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/1eae2c98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, Multiple Beds](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/9704ee61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Valley Inn [](https://www.expedia.ca/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information) West Hatfield 8.6/10 Excellent (104 reviews) "Very clean rooms and friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacalynn CA $136 CA $151 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/870ad54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) Lee 9.6/10 Exceptional (290 reviews) "A charming inn in the center of the Berkshires." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danny CA $197 CA $231 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/c3ce1b97.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/3a99baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Berkshire Inn [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) Pittsfield 7.8/10 Good (841 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 CA $117 CA $131 total includes taxes & fees Feb 25 - Feb 26 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1350000/1343800/1343727/a2bd31ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free self parking](https://images.trvl-media.com/lodging/2000000/1350000/1343800/1343727/555a884e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/2000000/1350000/1343800/1343727/21bc83a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1350000/1343800/1343727/a1bbe5d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elm Motel [](https://www.expedia.ca/Springfield-Hotels-Elm-Motel.h1343727.Hotel-Information) Westfield 7.2/10 Good (123 reviews) "Very clean, lacking bathroom and bathroom storage. Good price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Daniel CA $122 CA $136 total includes taxes & fees Jan 27 - Jan 28 [](https://www.expedia.ca/Springfield-Hotels-Elm-Motel.h1343727.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/05fa2663.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/5a448032.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Suite- NO PETS ALLOWED](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e75ce45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![50-inch flat-screen TV with cable channels, TV, streaming services](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/0e28a2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Central Downtown Inn & Suites [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) Pittsfield 8.6/10 Excellent (354 reviews) "Very helpful staff, clean and spacious rooms. Has everything you need - well equipped." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn CA $129 CA $144 total includes taxes & fees Feb 15 - Feb 16 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/5b50a276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/182327c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | Terrace/patio](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/26677985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | Private kitchen](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/062df4a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Becket Motel [](https://www.expedia.ca/Becket-Hotels-Becket-Motel.h27064222.Hotel-Information) Becket 6.8/10 (60 reviews) "Comfortable stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $121 CA $182 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Becket-Hotels-Becket-Motel.h27064222.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892600/892598/fc660f44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Down comforters, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/900000/892600/892598/a668b8c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/900000/892600/892598/d47c2eca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch LCD TV with cable channels, TV, pay movies](https://images.trvl-media.com/lodging/1000000/900000/892600/892598/b1bcd4d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Chicopee/Springfield [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-ChicopeeSpringfield.h892598.Hotel-Information) Chicopee 9.0/10 Wonderful (1,002 reviews) "Clean comfortable rooms, great breakfast, very nice staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $145 CA $164 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-ChicopeeSpringfield.h892598.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/f05f40a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/e59f44b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/71c77a60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds, Non Smoking, City View](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/3b33b8ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Springfield MA [](https://www.expedia.ca/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.Hotel-Information) Metro Center 8.0/10 Very good (1,314 reviews) "Breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Twain CA $151 CA $172 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.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.ca/Hotel-Search?startDate=2026-02-09&endDate=2026-02-10®ionId=6005399&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d6005399.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Hotels.d6005399.Travel-Guide-Hotels) ## Learn more about Chester Experience the hiking, camping, and riverfront in Chester! [See all hotels in Chester](https://www.expedia.ca/Hotel-Search?startDate=2026-02-09&endDate=2026-02-10&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 ### Stay near popular Chester attractions Chester, Massachusetts, offers a delightful blend of outdoor adventures and romantic scenery, making it an ideal vacation spot. Visitors can enjoy attractions such as urban parks, nature reserves, and historic houses. For a complete experience, don’t miss the Chester Racecourse, Chester Zoo, and the historic Chester Castle, as well as exploring the charming Chester city itself, perfect for families and adventure seekers alike. [](https://expedia.ca/Chester-Town-Hall-Hotels.0-l553248621532666604-0.Travel-Guide-Filter-Hotels) #### Chester Town Hall Chester Town Hall offers a rich cultural experience, showcasing stunning architecture and vibrant civic life, making it a must-visit for history and culture enthusiasts alike. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532666604) ## 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 CA $93 CA $107 total Feb 4 - Feb 5 includes taxes & fees 5.8/10 (1,001 reviews) [](https://expedia.ca/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 CA $108 CA $123 total Feb 11 - Feb 12 includes taxes & fees 7/10 Good! (1,002 reviews) [](https://expedia.ca/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 CA $115 CA $129 total Feb 8 - Feb 9 includes taxes & fees 8.2/10 Very Good! (1,001 reviews) [](https://expedia.ca/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 CA $116 CA $133 total Feb 4 - Feb 5 includes taxes & fees 6.8/10 (1,001 reviews) [](https://expedia.ca/Springfield-Hotels-Red-Roof-Inn-PLUS-West-Springfield.h27090.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 CA $122 CA $139 total Feb 1 - Feb 2 includes taxes & fees 8.8/10 Excellent! (1,002 reviews) [](https://expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.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 CA $156 CA $174 total Feb 17 - Feb 18 includes taxes & fees 7/10 Good! (1,000 reviews) [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.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.ca/4Star-Chester-Hotels.s40-0-d6005399.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 117 properties [](https://expedia.ca/3Star-Chester-Hotels.s30-0-d6005399.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 101 properties [](https://expedia.ca/2Star-Chester-Hotels.s20-0-d6005399.Travel-Guide-Filter-Hotels) ## Find out more about Chester ### Top reasons to visit Chester - **Outdoor Adventures:** Chester offers stunning scenery perfect for hiking, golfing, and exploring nature reserves. - **Historic Attractions:** Don't miss the iconic Chester Castle and the charming city centre steeped in history. - **Live Performances:** Enjoy a variety of theatre performances and music concerts for an engaging cultural experience. - **Family-Friendly Activities:** Chester provides a welcoming atmosphere with options for both relaxation and recreation. - **Diverse Accommodations:** Choose from cozy bed and breakfasts to comfortable hotels, catering to every traveller's needs. ### Find great hotels in Chester Discover the charm of Chester, Massachusetts, with a variety of hotel accommodations to suit every traveller's needs. Whether you're seeking a cozy bed and breakfast, a budget-friendly option, or a comfortable 4-star hotel, Chester has it all. Enjoy pet-friendly amenities, adventure-themed experiences, and business-friendly facilities, ensuring a memorable stay in this picturesque town. - **The Black Swan Lee - Lenox, Ascend Hotel Collection:** Nestled 24.1km from Chester, The Black Swan Lee - Lenox is a charming 3-star hotel that caters to families, adventure seekers, and pet lovers alike. This property is an excellent choice for those looking to immerse themselves in outdoor activities, offering a range of adventure sports such as onsite fishing and nearby skiing lessons. Families will appreciate the thoughtful amenities designed for children, including first aid kits and cribs available upon request. Moreover, pets are welcome with certain restrictions, ensuring that your furry friends can join in on the fun. - **[Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG:](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)** This 3.5-star resort, located 24.1km from Chester, is perfect for families, skiing enthusiasts, and adventure lovers. With convenient access to ski shuttles and lifts, guests can easily explore the snowy slopes. The resort boasts a variety of recreational activities, including onsite mini-golf and an arcade game room for children. For those seeking outdoor thrills, skiing, snow tubing, and hiking options are available nearby. The welcoming environment and family-friendly amenities make this resort a fantastic home base for your Berkshires adventure. - **[Hampton Inn & Suites Berkshires-Lenox:](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information)** Situated 27.4km from Chester, Hampton Inn & Suites Berkshires-Lenox offers a blend of adventure, business amenities, and pet-friendly options. This hotel is ideal for business travellers, featuring a well-equipped 24-hour business centre and conference space. Adventure awaits with nearby skiing, snowshoeing, and biking trails. The welcoming atmosphere extends to furry companions, accommodating dogs and cats with designated exercise areas. Guests will enjoy the modern comforts alongside attentive service, making it a great choice for both work and relaxation. ### Where to stay in Chester Chester, Massachusetts, is a charming destination ideal for outdoor enthusiasts and romantic getaways. Explore the picturesque Chester city centre, steeped in history and surrounded by beautiful scenery. Nearby regions offer a family-friendly atmosphere perfect for relaxation and recreation. Don't miss the chance to visit historic sites and enjoy the serene vibes of this delightful town. Whether you're seeking adventure or tranquility, Chester has something special for every type of traveller. - **[Lenox:](https://www.expedia.ca/Lenox-Hotels.d8587.Travel-Guide-Hotels)** Nestled 27.4km from Chester, Lenox is a charming city renowned for its vibrant cultural scene. With seasonal visitor peaks from June to August, this destination offers a delightful mix of entertainment, romance, and family experiences. Visitors can enjoy live music concerts, captivating theatre performances, and winter skiing adventures. Nature enthusiasts will appreciate the stunning lakes and mountains that surround the area, making it a perfect spot for outdoor activities year-round. Don't miss the local event conference venues that host various exciting gatherings throughout the year. - **[Sherwood Forest:](https://www.expedia.ca/Sherwood-Forest-Becket-Hotels.0-n553248635976472129-0.Travel-Guide-Filter-Hotels)** A serene neighborhood located 8.0km from Chester, Sherwood Forest is an idyllic escape with a relaxed atmosphere. While visitor numbers peak in July to August and October, this area offers year-round allure for those seeking romance, outdoor activities, and beautiful scenery. Enjoy the recreational areas and nearby theatres that offer captivating performances. The local highlights include picturesque lakes, a lively stadium, and a thrilling theme park, providing ample opportunities for fun and relaxation amidst nature’s beauty. - **[Becket:](https://www.expedia.ca/Becket-Hotels.d6005395.Travel-Guide-Hotels)** Situated a mere 9.7km from Chester, Becket is a delightful city that attracts visitors with its blend of romance, outdoor adventures, and entertainment. Peak travel periods occur from June to August, making it an ideal summer getaway. Becket boasts a variety of engaging activities, including theatre productions, live music concerts, and skiing at local fields. Nature lovers will enjoy the stunning lakes, majestic mountains, and the nearby national state park, offering plenty of opportunities for hiking and exploring the great outdoors. ### Things to do in Chester Chester, Massachusetts, is perfect for an outdoor, romantic getaway surrounded by stunning scenery. Enjoy activities like theatre performances and music concerts, or explore local educational experiences. Don't miss a visit to Chester Castle, a round of golf at the local course, and the convenience of tour buses for trips from Chester. Plan an exciting day filled with exploration, making the most of your time in this charming town. **Shopping** For a delightful shopping experience in Chester, visit the Berkshire Mountain Country Store or explore Guido's Marketplace for unique finds. If you're up for a drive, the Lee Premium Outlets offer a variety of brand-name deals just 20.9km away, perfect for gift shopping. **Recreation** Experience the artistry of dance at [Jacob's Pillow](https://www.expedia.ca/Jacobs-Pillow-Hotels.0-l553248621532666599-0.Travel-Guide-Filter-Hotels), a cultural gem located 11.3km from Chester, where romance and entertainment meet. For a serene escape, visit [Goose Pond Reservation](https://www.expedia.ca/Goose-Pond-Reservation-Hotels.0-l6339855-0.Travel-Guide-Filter-Hotels), 17.7km away, offering wellness and relaxation amidst nature's beauty. Enjoy outdoor sports at [Wyndhurst Golf & Club](https://www.expedia.ca/Wyndhurst-Golf-Club-Hotels.0-l553248621532665266-0.Travel-Guide-Filter-Hotels), 24.1km distant. **Adventure** Experience the thrill of skiing at [Blandford Ski Area](https://www.expedia.ca/Blandford-Ski-Area-Hotels.0-l553248621532666606-0.Travel-Guide-Filter-Hotels), located 11.3km from Chester, where you can enjoy invigorating slopes. For a scenic hike, the [Skyline Trail](https://www.expedia.ca/Skyline-Trail-Hotels.0-l553248621532666608-0.Travel-Guide-Filter-Hotels) offers outdoor adventure and captivating views, only 11.3km away. For more skiing excitement, head to [Berkshire East Ski Resort](https://www.expedia.ca/Berkshire-East-Ski-Resort-Hotels.0-l553248621532666707-0.Travel-Guide-Filter-Hotels), 38.6km from Chester. **Nightlife** Experience the charm of Chester's nightlife by catching a performance at [Shakespeare and Company](https://www.expedia.ca/Shakespeare-And-Company-Hotels.0-l6127086-0.Travel-Guide-Filter-Hotels), only 25.7km away, or enjoy family fun at [Spare Time Bowling](https://www.expedia.ca/Spare-Time-Bowling-Hotels.0-l553248621532666629-0.Travel-Guide-Filter-Hotels), 29.0km away. For a romantic evening, visit the [Academy of Music Theater](https://www.expedia.ca/Academy-Of-Music-Theater-Hotels.0-l6070271-0.Travel-Guide-Filter-Hotels), also 29.0km from Chester. ### Booking tips and Expedia advantages for Chester To save money during your visit to Chester, Massachusetts, consider exploring free attractions like Chester Town Hall, Pyramid Lake, and the Becket Land Trust Historic Quarry. The most affordable months to visit are March and December to January, while Tuesdays typically offer the lowest hotel rates. Use Expedia's search tool to find budget accommodations and consider package deals that combine flights, hotels, and activities for additional savings. Look for eco-friendly hotels to ensure sustainable options that fit your budget. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Chester are March and December to January, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Chester is Tuesday. The most expensive day to stay in Chester is Saturday. - **Find cheap hotels on Expedia:** Expedia's search tool enables you to specify your budget, desired location, and additional preferences. You can arrange your search results to display prices from lowest to highest, ensuring you see the most affordable hotels first. Additionally, you have the option to narrow down your choices by hotel type; for instance, selecting the "Eco-certified" filter will showcase sustainable and environmentally friendly hotels that you can book. - **Consider bundling your trip:** You can save money by combining your Chester hotel reservation with your flights and activities through an Expedia package. ### Best time to go to Chester Visitor numbers in Chester is generally unchanged in popularity throughout the year. The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are average and weather is mostly cloudy with light rain. | **![calendar icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly cloudy icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation rate icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --------------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------------------- | --------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------------------ | ------------------------------------------------------------------------------------------------------------------ | | January | 23.5°F (-4.7°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 25.3°F (-3.7°C) | Light Rain | Mostly Cloudy | Slightly Low | Average | | March | 33.1°F (0.6°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | April | 44.8°F (7.1°C) | Light Rain | Mostly Cloudy | Average | Average | | May | 56.5°F (13.6°C) | Light Rain | Mostly Sunny | Average | Average | | June | 64.4°F (18.0°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 70.5°F (21.4°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 68.7°F (20.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | September | 61.9°F (16.6°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 50.7°F (10.4°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 38.8°F (3.8°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 30.2°F (-1.0°C) | Light Rain | Mostly Cloudy | Slightly Low | Slightly Low | ### The nearest major airports for your trip to Chester To visit Chester, Massachusetts, the nearest major airports are Hartford, CT ([BDL](https://www.expedia.ca/Bradley-Intl-Airport-Hotels.0-aBDL-0.Travel-Guide-Filter-Hotels)\-Bradley Intl.), Albany, NY ([ALB](https://www.expedia.ca/Albany-Intl-Airport-Hotels.0-aALB-0.Travel-Guide-Filter-Hotels)\-Albany Intl.), and Worcester, MA ([ORH](https://www.expedia.ca/Worcester-Regional-Airport-Hotels.0-aORH-0.Travel-Guide-Filter-Hotels)\-Worcester Regional). Bradley International Airport is approximately 45.1km away, with nearby hotels such as the [DoubleTree by Hilton Hartford - Bradley Airport](https://www.expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.Hotel-Information), just 1.6km from the airport. Albany International Airport is 85.3km from Chester, offering options like [The Landing Hotel at Rivers Casino & Resort](https://www.expedia.ca/Albany-Hotels-The-Landing-Hotel-At-Rivers-Casino-Resort.h19093277.Hotel-Information), 12.9km away. Worcester Regional Airport is situated 91.7km from Chester, with accommodations like the [Beechwood Hotel](https://www.expedia.ca/Worcester-Hotels-Beechwood-Hotel.h26897.Hotel-Information), located 8.0km from the airport. All these hotels provide accessible transportation to their respective airports. ## Recent reviews of Chester hotels ![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21_y.jpg) ### Tru by Hilton Chicopee Springfield 5/5 Excellent "Amazing service and professional customer service was outstanding " A verified traveller stayed at Tru by Hilton Chicopee Springfield Posted 2 days ago [](https://expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.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 5/5 Excellent "Clean and comfortable rooms including a massage chair. Fresh baked cookies daily. Very friendly staff...every single one of them. Fresh muffins baked for continental breakfast, but I missed them because I woke up late every day...lol" A verified traveller stayed at Blue – A Modern Hotel, an Ascend Collection Hotel Posted 3 days ago [](https://expedia.ca/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 5/5 Excellent "The room was large, clean and comfortable. The breakfast was good and the staff was great. The hotel is a little bit quaint which I enjoy and why I go there. The only issue was the shower took a while for the water to heat up." A verified traveller from Syracuse stayed at The Red Lion Inn Posted 4 days ago [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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 5/5 Excellent "Fro t desk staff was wonderful and Very helpful’" A verified traveller stayed at The Yankee, Trademark Collection by Wyndham Posted 4 days ago [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 5/5 Excellent "Great, great place!" A verified traveller stayed at D. Hotel Suites & Spa Posted 4 days ago [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 5/5 Excellent "Beautiful unique property! Very clean room and very friendly staff" A verified traveller stayed at Berkshires Untold Posted 5 days ago [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Hotel Northampton](https://images.trvl-media.com/lodging/1000000/20000/17900/17876/fe4b5272_y.jpg) ### Hotel Northampton 5/5 Excellent "The room was great. Very friendly saff." A verified traveller stayed at Hotel Northampton Posted 5 days ago [](https://expedia.ca/Springfield-Hotels-Hotel-Northampton.h17876.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 5/5 Excellent "The staff is super friendly and accommodating. The location is quiet. We stayed during the winter, but the lake view from the restaurant and breakfast area were really nice. The hotel was well kept and clean. We’ll definitely stay there again. " A verified traveller stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel Posted 7 days ago [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 5/5 Excellent "Clean, great location near Bosquet Mountain and grocery store, spacious condo, easy. " A verified traveller from Doylestown stayed at Berkshire Mountain Lodge Posted 7 days ago [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ## Frequently asked questions ### What's the best place to stay in Chester? ### What are some of the best vacation rentals in Chester? ### If I need to cancel my hotel reservation in Chester, will I receive a refund? ### What is staying in Chester like? ### What should I see while I'm in Chester? ### What's the seasonal weather like in Chester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [3 Star Hotels in Otis ](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - [B&B in Becket ](https://www.expedia.ca/Becket-Bed-And-Breakfast.d6005395-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Becket ](https://www.expedia.ca/Becket-Chalets.d6005395-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Becket ](https://www.expedia.ca/Becket-Guest-Houses.d6005395-aaGuestHouses.Travel-Guide-Accommodation) - 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