Title: Book The Best Hotels in Chester, MA for 2025 from CA $120 - 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) ![Frozen Sanderson Brook Falls in Chester ](https://images.trvl-media.com/place/6005399/400cb5cc-e1d2-4765-9a2f-8870b6e8f711.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Elizabeth Massa Peroulakis # Find hotels in Chester, MA from CA $120 - ![](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 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=2025-12-03&d1=2025-12-03&endDate=2025-12-05&d2=2025-12-05&lodging=AGRITOURISM) 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=2025-12-03&d1=2025-12-03&endDate=2025-12-05&d2=2025-12-05&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=2025-12-03&d1=2025-12-03&endDate=2025-12-05&d2=2025-12-05&amenities=POOL) 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=2025-12-03&d1=2025-12-03&endDate=2025-12-05&d2=2025-12-05&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=2025-12-03&d1=2025-12-03&endDate=2025-12-05&d2=2025-12-05&lodging=APARTMENT) 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=2025-12-03&d1=2025-12-03&endDate=2025-12-05&d2=2025-12-05&amenities=PETS) 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=2025-12-03&d1=2025-12-03&endDate=2025-12-05&d2=2025-12-05&lodging=COTTAGE) ## Check prices for these dates Tonight [Nov 19 - Nov 20](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-19&endDate=2025-11-20&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 20 - Nov 21](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-20&endDate=2025-11-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 840 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/4fd790fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel Lee 9.0/10 Wonderful (1000) "The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elisabeth CA $153 CA $171 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.2/10 Wonderful (1005) "Great stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ann CA $107 CA $120 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold Lenox 9.0/10 Wonderful (799) "We had a nice room and the food was delicious. Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vincent CA $126 CA $141 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/6d13ff43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/77c211db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 2 Double Beds](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/781f36ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/51c29111.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites West Springfield by IHG West Springfield 8.4/10 Very good (785) "Nice, friendly staff, clean room and comfortable suite.. highly recommend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christopher CA $137 CA $157 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Springfield-Hotels-Candlewood-Suites-West-Springfield.h897535.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.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/a25612d3.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/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (962) "Staff was very nice and helpful nice place restaurant was awesome great food and drinks" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frank CA $124 CA $138 total includes taxes & fees Nov 21 - Nov 22 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed | Living area](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/d32c867e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a02c1cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a5a66acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cornell Inn, Lenox & The Berkshires Lenox 9.0/10 Wonderful (1001) "Overall a really fun place to stay. Rooms were good quality and the staff was welcoming and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacob CA $176 CA $251 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/27100/27090/23b7c14f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27100/27090/a015e989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Room, 1 King Bed (Upgraded Bedding & Snack, Smoke Free)](https://images.trvl-media.com/lodging/1000000/30000/27100/27090/71fd75df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pillowtop beds, desk, blackout drapes, free WiFi](https://images.trvl-media.com/lodging/1000000/30000/27100/27090/26decad7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Red Roof Inn PLUS+ West Springfield West Springfield 6.8/10 (1003) "Great like always " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharee CA $116 CA $133 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Springfield-Hotels-Red-Roof-Inn-PLUS-West-Springfield.h27090.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 indoor pools, 2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/3c0625c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG South Lee 9.0/10 Wonderful (786) "Place was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin CA $178 CA $219 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d969459c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/9b7b4cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds (Main Inn)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1001) "I love the ambience - historic and comfortable and excellent food. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nancy CA $208 CA $295 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Basic Studio, 1 King Bed](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/b05651fb.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) ![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) ### River Valley Inn West Hatfield 8.6/10 Excellent (97) "Clean room, comfortable bed, nice shower! Owners were very nice - we will definitely stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deb CA $148 CA $165 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/7f7ace74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/54ca314e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/bd574b66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/85e43da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn West Springfield West Springfield 7.0/10 Good (1011) "Room and staff were good " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) George CA $121 CA $139 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/71c77a60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed with Sofa bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/818811dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/0c5163c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/25c325c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Quinta Inn & Suites by Wyndham Springfield MA Metro Center 8.2/10 Very good (1295) "Great staff, very clean property, and good breakfast. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jasmine CA $150 CA $170 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/f450d89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/670699cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/b51475ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge Pittsfield 9.0/10 Wonderful (759) "All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/67e1adab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/617da859.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/2b026b4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG Pittsfield 9.4/10 Exceptional (60) "Very clean room, courteous staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeffrey CA $147 CA $165 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/a37fc75b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/cab085ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### D. Hotel Suites & Spa Holyoke 9.4/10 Exceptional (2251) "Very clean room, great variety of food at breakfast, friendly and helpful staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Liz CA $154 CA $179 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/62ab3ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/11bb9318.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG Great Barrington 8.8/10 Excellent (695) "Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tabitha CA $150 CA $167 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/651f878e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c3ea2282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North Pittsfield 9.6/10 Exceptional (798) "Clean room and staff was super friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yuen CA $208 CA $233 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.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) ![Fire Spa Suite | Room amenity](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/af4baaa3.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) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/a6853cfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chambery Inn Lee 9.6/10 Exceptional (372) "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) ![Lobby](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/e6abed3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/f8a21b1d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/2ea82ad5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/9000000/8450000/8449800/8449737/aae7cd6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites Springfield Northampton/Amherst Northampton 9.2/10 Wonderful (1003) "Clean room great breakfast selections would stay here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $200 CA $223 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Springfield-Hotels-Fairfield-Inn-Suites-Springfield-NorthamptonAmherst.h8449737.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/8c645106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/eaa5d51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/5c3a2624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Courtyard by Marriott West Springfield West Springfield 9.2/10 Wonderful (567) "Room was clean and staff was super friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessuca CA $165 CA $189 total includes taxes & fees Nov 26 - Nov 27 [](https://www.expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.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=2025-12-03&endDate=2025-12-04®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 forests in Chester! [See all hotels in Chester](https://www.expedia.ca/Hotel-Search?startDate=2025-12-03&endDate=2025-12-04&adults=2®ionId=6005399) ![Frozen Sanderson Brook Falls in Chester ](https://images.trvl-media.com/place/6005399/400cb5cc-e1d2-4765-9a2f-8870b6e8f711.jpg?impolicy=fcrop&w=300&h=400&p=1&q=high) Photo by Elizabeth Massa Peroulakis ### Stay near popular Chester attractions [](https://expedia.ca/Chester-Town-Hall-Hotels.0-l553248621532666604-0.Travel-Guide-Filter-Hotels) #### 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://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532666604) ## More cheap stays in Chester ![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 $121 CA $139 total Dec 17 - Dec 18 includes taxes & fees 7/10 Good! (1,004 reviews) [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.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 Dec 1 - Dec 2 includes taxes & fees 6.8/10 (1,002 reviews) [](https://expedia.ca/Springfield-Hotels-Red-Roof-Inn-PLUS-West-Springfield.h27090.Hotel-Information) ![Quality Inn & Suites Northampton - Amherst](https://images.trvl-media.com/lodging/1000000/30000/24600/24588/f86e1269_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn & Suites Northampton - Amherst 117 Conz St Northampton MA CA $165 CA $185 total Dec 1 - Dec 2 includes taxes & fees 7/10 Good! (1,002 reviews) [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information) ![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 $107 CA $123 total Dec 7 - Dec 8 includes taxes & fees 5.8/10 (999 reviews) [](https://expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-West-SpringfieldRoute-5.h459711.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 $138 total Dec 1 - Dec 2 includes taxes & fees 8.8/10 Excellent! (1,000 reviews) [](https://expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.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 $130 CA $145 total Dec 14 - Dec 15 includes taxes & fees 8.2/10 Very Good! (1,000 reviews) [](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.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 115 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 87 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 ### Homewood Suites by Hilton Hadley Amherst 5/5 Excellent "Clean room, spacious room, nice staff, and good location for our trip. " A verified traveller stayed at Homewood Suites by Hilton Hadley Amherst Posted 2 days ago [](https://expedia.ca/Springfield-Hotels-Homewood-Suites-By-Hilton-Hadley-Amherst.h33232831.Hotel-Information) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 5/5 Excellent "Everything was amazing my bf did get a beer at the bar that was expired but everything else was amazing " A verified traveller stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG Posted 3 days ago [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ### Quality Inn West Springfield 5/5 Excellent "Very courteous staff. Comfortable, clean room. Always interesting people travelling through." A verified traveller stayed at Quality Inn West Springfield Posted 4 days ago [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ### The Yankee, Trademark Collection by Wyndham 5/5 Excellent "Great stay!" 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) ### Berkshire Mountain Lodge 5/5 Excellent "The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway " A verified traveller stayed at Berkshire Mountain Lodge Posted 5 days ago [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ### Courtyard by Marriott West Springfield 5/5 Excellent "Work trip meet my needs" A verified traveller stayed at Courtyard by Marriott West Springfield Posted 5 days ago [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 5/5 Excellent "The room was nice, but wish we would have asked for the lake view. The breakfast area was really nice and they had good food. The coffee machine was available 24/7 and it made a pretty good mocha! " 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) ### The Ellery 5/5 Excellent "I stayed in a double queen room with my daughter on a visit to Smith. The room was very comfortable, the host was delightful l, and the breakfast was delicious! Will be back!" A verified traveller stayed at The Ellery Posted 7 days ago [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ### Quality Inn Westfield - Springfield 5/5 Excellent "Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet." A verified traveller stayed at Quality Inn Westfield - Springfield Posted 8 days ago [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information) ## Frequently asked questions ### What's the best place to stay in Chester? > [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), located 22.9 mi (36.8 km) from the heart of Chester, is a top choice for your stay based on our traveler data. Other good choices for your trip to the area are [Berkshire Mountain Lodge](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) and [Quality Inn West Springfield](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information). See all available [top hotels](https://www.expedia.ca/Hotel-Search?regionId=6005399), or [vacation rentals in Chester](https://www.expedia.ca/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals). ### What are some of the best vacation rentals in Chester? > [Pet Friendly Riverfront Home in Great Barrington](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information): This vacation home rental outside of Chester is located on a river and has a fireplace, a garden, and laundry facilities to put you at ease in your new surroundings. It has 3 bedrooms in addition to a kitchen with a stovetop and a microwave. You and your friends and family can relax into your vacation with amenities like a selection of games. See all [vacation rentals in Chester](https://www.expedia.ca/Chester-Vacation-Rentals.d6005399.Travel-Guide-VacationRentals). ### If I need to cancel my hotel reservation in Chester, will I receive a refund? > Yes! Most hotel bookings are fully refundable as long as you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of your check-in date. If you have a non-refundable reservation, it may still be possible to cancel it and get a refund within a 24-hour period of your booking. Filter your search by [fully refundable](https://www.expedia.ca/Hotel-Search?regionId=6005399&paymentType=FREE_CANCELLATION) to find flexible hotel deals in Chester. ### What is staying in Chester like? > Visitors can enjoy all that Chester has to offer including the waterfalls, shopping, and riverfront. Tourists can also enjoy the city's restaurants, theaters, and monuments. In Chester, there are 2 hotels and other accommodations to choose from. Find out more about [Chester](https://www.expedia.ca/Chester.dx6005399). ### What should I see while I'm in Chester? > A favorite place to visit is [Chester Town Hall](https://www.expedia.ca/Chester-Town-Hall-Chester.d553248621532666604.Vacation-Attraction). You'll also find [Littleville Lake](https://www.expedia.ca/Littleville-Lake-Huntington.d553248621532666607.Vacation-Attraction) and [Pyramid Lake](https://www.expedia.ca/Pyramid-Lake-Becket.d553248621532647064.Vacation-Attraction) in the area. Check out what more to see and do in Expedia's [Chester guide](https://www.expedia.ca/Chester.dx6005399). ### What's the seasonal weather like in Chester? > The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. 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Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)