Title: Book The Best Hotels in Chester, MA for 2026 from CA $84 - 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) ![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__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=2026-03-27&d1=2026-03-27&endDate=2026-03-29&d2=2026-03-29&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=2026-03-27&d1=2026-03-27&endDate=2026-03-29&d2=2026-03-29&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=2026-03-27&d1=2026-03-27&endDate=2026-03-29&d2=2026-03-29&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=2026-03-27&d1=2026-03-27&endDate=2026-03-29&d2=2026-03-29&amenities=HOT_TUB) 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=2026-03-27&d1=2026-03-27&endDate=2026-03-29&d2=2026-03-29&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=2026-03-27&d1=2026-03-27&endDate=2026-03-29&d2=2026-03-29&lodging=COTTAGE) ## Check prices for these dates Tonight [Mar 13 - Mar 14](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-03-13&endDate=2026-03-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 14 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-03-14&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-03-13&endDate=2026-03-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-03-20&endDate=2026-03-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Chester hotels ![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) ![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) ![Lobby](https://images.trvl-media.com/lodging/1000000/860000/856300/856259/5fdae7fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/860000/856300/856259/19f55017.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 (855 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 $123 CA $139 total includes taxes & fees Apr 6 - Apr 7 [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-Chicopee-Springfield.h856259.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/2000000/1680000/1673200/1673139/8cf443f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mort's Library](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/f25262f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Global Fusion)](https://images.trvl-media.com/lodging/2000000/1680000/1673200/1673139/8b862974.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 (429 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 $137 CA $156 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Springfield-Hotels-Naomis-Inn-Bed-Breakfast.h1673139.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) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/1690062a.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) ### FairBridge Inn Express [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information) Pittsfield 5.4/10 (812 reviews) "Room spotless and staff helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $97 CA $108 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/fd5f12a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/f0e5252a.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) ### Econo Lodge Lee - Great Barrington [](https://www.expedia.ca/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information) Lee 6.4/10 (659 reviews) "Good to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ibinabo CA $75 CA $84 total includes taxes & fees Apr 3 - Apr 4 [](https://www.expedia.ca/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.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) ![Lobby](https://images.trvl-media.com/lodging/7000000/6260000/6250400/6250331/d0c6a158.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 (488 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 $195 CA $222 total includes taxes & fees Mar 30 - Mar 31 [](https://www.expedia.ca/Springfield-Hotels-Residence-Inn-Springfield-Chicopee.h6250331.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) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759009/2e09a8f3.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 $421 CA $509 total includes taxes & fees Mar 28 - Mar 29 [](https://www.expedia.ca/Stockbridge-Hotels-Stockbridge-Country-Inn.h2759009.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) ![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) ![Fire Spa Suite](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/de897732.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) ### Chambery Inn [](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) Lee 9.6/10 Exceptional (376 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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892600/892598/dcb9c41b.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 $150 CA $171 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-ChicopeeSpringfield.h892598.Hotel-Information) ![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) ![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) ![Basic Double Room](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/db3c3dee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Sunset Inn [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) Lee 7.6/10 Good (411 reviews) "owners was nice, room was clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) tom CA $129 CA $144 total includes taxes & fees Mar 21 - Mar 22 [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) ![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) ![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) ![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) ![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) ### Devonfield Inn B&B [](https://www.expedia.ca/Lee-Hotels-Devonfield-Inn-BB.h1575232.Hotel-Information) Lee 10/10 Exceptional (136 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) ![Exterior](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/a50fdd34.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) ![Studio Suite, Multiple Beds](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/b2e93f7c.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) ### River Valley Inn [](https://www.expedia.ca/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information) West Hatfield 8.4/10 Very good (118 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 CA $136 CA $152 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/35000000/34820000/34814400/34814366/fc57caa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daniel Stebbins Room #2](https://images.trvl-media.com/lodging/35000000/34820000/34814400/34814366/79ed918f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/35000000/34820000/34814400/34814366/96e39ce4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34820000/34814400/34814366/522cc3ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Daniel Stebbins House [](https://www.expedia.ca/South-Hadley-Hotels-Daniel-Stebbins-Bed-And-Breakfast.h34814366.Hotel-Information) South Hadley 10/10 Exceptional (51 reviews) "Quaint B&B in the heart of South Hadley. Within walking distance of town and Mount Holyoke College. (Stairs to second floor are a bit steep for anyone with accessibility issues.) Great overall local place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jason CA $368 CA $411 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/South-Hadley-Hotels-Daniel-Stebbins-Bed-And-Breakfast.h34814366.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1510000/1502200/1502130/c5b973e1.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) ### 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 $325 CA $381 total includes taxes & fees Mar 14 - Mar 15 [](https://www.expedia.ca/Stockbridge-Hotels-The-Inn-At-Stockbridge.h1502130.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) ![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) ![Hypo-allergenic bedding, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/e88abd9f.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) ### 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 (1,000 reviews) "Staff was very courteous and rooms clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steven CA $166 CA $186 total includes taxes & fees Mar 14 - Mar 15 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/3a99baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, Accessible](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) ### Berkshire Inn [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) Pittsfield 7.8/10 Good (847 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 $109 CA $122 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ![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) ![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 | Private kitchen](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/9e3d1bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/e51296ab.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 $118 CA $178 total includes taxes & fees Apr 1 - Apr 2 [](https://www.expedia.ca/Becket-Hotels-Becket-Motel.h27064222.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/d652d2fd.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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/e4c803ed.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 (358 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 $139 CA $155 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Pittsfield-Hotels-Yankee-Suites-Extended-Stay.h1457797.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) ![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) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.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 (294 reviews) "Friendly staff, great location, beautiful views, cozy room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $187 CA $220 total includes taxes & fees Mar 20 - Mar 21 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/13980508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/w4000h2665x0y2-3046acd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/cb762de9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/40000/34300/34260/07d4dc21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### TownePlace Suites by Marriott Hadley Amherst [](https://www.expedia.ca/Hadley-Hotels-TownePlace-Suites-By-Marriott-Hadley-Amherst.h34260.Hotel-Information) Hadley 9.8/10 Exceptional (73 reviews) "Loved that I could bring my dog! Large comfortable room and friendly staff! Great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pauline CA $207 CA $231 total includes taxes & fees Mar 19 - Mar 20 [](https://www.expedia.ca/Hadley-Hotels-TownePlace-Suites-By-Marriott-Hadley-Amherst.h34260.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/bb79982b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/b3ee4f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Private Bathroom (Field of Dreams)](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/903dd1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) Cheshire 9.4/10 Exceptional (53 reviews) "Nice place for a weekend away." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gregory CA $318 CA $337 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Cheshire-Hotels-Harbour-House-Inn.h17326568.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=2026-03-27&endDate=2026-03-28®ionId=6005399&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/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.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) ## Stay near popular Chester attractions ### Chester Town Hall You can get tickets for a performance at Chester Town Hall during your trip to Chester. Wander the lakeside and forest in this relaxing area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532666604) ## Learn more about Chester Experience the hiking, camping, and monuments in Chester! [See all hotels in Chester](https://www.expedia.ca/Hotel-Search?startDate=2026-03-27&endDate=2026-03-28&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 ## Recent Reviews in Chester ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb_y.jpg) ### Berkshires Untold 8/10 Good "Room was clean. Redone motel" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/143e42a0_y.jpg) ### The Ellery 8/10 Good "Have stayed many times as convenient to our friends in area..this time on ground floor and we're awakened at 6:30 by dumpster being emptied ..ugh... Choose an second floor room and also avoid having to walk outside to go to lobby for brkfst..raining & cold this morning 😞" [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.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 "Easy check-in; accommodating staff; clean room. Convenient but also quiet location." [](https://expedia.ca/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/bca96d17_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 8/10 Good "Nice place to stay. Beautiful pond and lovely continental breakfast " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Baldwin Inn & Suites, SureStay Collection by Best Western](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-3661e0ca_y.jpg) ### Baldwin Inn & Suites, SureStay Collection by Best Western 10/10 Excellent "Friendly, clean and comfortable. " [](https://expedia.ca/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) ![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/27ce1034_y.jpg) ### Courtyard by Marriott Lenox Berkshires 10/10 Excellent "Clean room, friendly and helpful staff. " [](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "the room was huge - we loved it!!" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "This has become our company's preferred hotel for business trips to the Holyoke/Northampton area. It is clean, quiet, safe, convenient, and the breakfast is stellar." [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Courtyard by Marriott West Springfield](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b_y.jpg) ### Courtyard by Marriott West Springfield 10/10 Excellent "Clean and efficient. Great location to find a meal and get away from the Big E chaos." [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ## More cheap stays in Chester ![Quality Inn West Springfield](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/58b2bc45_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn West Springfield 1150 Riverdale St West Springfield MA CA $106 CA $121 total Mar 26 - Mar 27 includes taxes & fees 7/10 Good! (1,001 reviews) [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![Baldwin Inn & Suites, SureStay Collection by Best Western](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5755h3840x5y0-3661e0ca_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Baldwin Inn & Suites, SureStay Collection by Best Western 21 Baldwin Street West Springfield MA CA $119 CA $136 total Mar 15 - Mar 16 includes taxes & fees 7.8/10 Good! (129 reviews) [](https://expedia.ca/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) ![Best Western Springfield West Inn](https://images.trvl-media.com/lodging/1000000/20000/14200/14144/a76d0174_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Springfield West Inn 429 Riverdale Street West Springfield MA CA $120 CA $137 total Mar 15 - Mar 16 includes taxes & fees 7.8/10 Good! (1,003 reviews) [](https://expedia.ca/Springfield-Hotels-Best-Western-Springfield-West-Inn.h14144.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Yankee, Trademark Collection by Wyndham 461 Pittsfield Rd Lenox MA CA $126 CA $141 total Mar 22 - Mar 23 includes taxes & fees 9.2/10 Wonderful! (1,001 reviews) [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Tru by Hilton Chicopee Springfield](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/b9956cb4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Tru by Hilton Chicopee Springfield 440 Memorial Dr Chicopee MA CA $144 CA $163 total Mar 22 - Mar 23 includes taxes & fees 9/10 Wonderful! (1,003 reviews) [](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?impolicy=resizecrop&rw=402&ra=fit) ### Blue – A Modern Hotel, an Ascend Collection Hotel 1080 Riverdale St West Springfield MA CA $160 CA $184 total Apr 13 - Apr 14 includes taxes & fees 9.6/10 Exceptional! (161 reviews) [](https://expedia.ca/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.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. ## 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 - 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) - [Cheap Hotels in Becket ](https://www.expedia.ca/Becket-Hotels-Cheap-Hotels.0-0-d6005395-tCheapHotels.Travel-Guide-Filter-Hotels) - 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