Title: Book The Best Hotels in Chester, MA for 2025 from CA $105 - Competitive Prices - 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 $105 ![](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=2025-11-07&d1=2025-11-07&endDate=2025-11-09&d2=2025-11-09&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=2025-11-07&d1=2025-11-07&endDate=2025-11-09&d2=2025-11-09&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=2025-11-07&d1=2025-11-07&endDate=2025-11-09&d2=2025-11-09&amenities=HOT_TUB) 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=2025-11-07&d1=2025-11-07&endDate=2025-11-09&d2=2025-11-09&amenities=PETS) 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=2025-11-07&d1=2025-11-07&endDate=2025-11-09&d2=2025-11-09&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=2025-11-07&d1=2025-11-07&endDate=2025-11-09&d2=2025-11-09&lodging=COTTAGE) ## Check prices for these dates Tonight [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-10-24&endDate=2025-10-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-10-25&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 841 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel Lee 9.2/10 Wonderful (1004) "Great Indian restaurant in the hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chris CA $149 CA $166 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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) ![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/77000000/76300000/76297700/76297618/967b0257.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 (774) "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 $130 CA $145 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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) ![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) ![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) ![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 9.0/10 Wonderful (1019) "Good breakfast King rooms are the best facing the mountains Recently remodeled " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan M CA $177 CA $198 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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/1000000/10000/2100/2067/207845f4.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) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (917) "Enjoyable stay. Staff were very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claire CA $144 CA $161 total includes taxes & fees Nov 2 - Nov 3 [](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) ![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) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a02c1cad.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) ### The Cornell Inn, Lenox & The Berkshires Lenox 9.0/10 Wonderful (1000) "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 $179 CA $254 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.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) ![Exterior](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/a50fdd34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/83622709.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) ### River Valley Inn West Hatfield 8.6/10 Excellent (83) "Great quiet motel. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hector CA $166 CA $186 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/West-Hatfield-Hotels-Hatfield-Inn.h107579521.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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/27100/27090/6e996aa7.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 (1002) "The staff was very helpful and nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cristal CA $137 CA $157 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Springfield-Hotels-Red-Roof-Inn-PLUS-West-Springfield.h27090.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) ![Gazebo](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/1d1dace5.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/77c211db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Candlewood Suites West Springfield by IHG West Springfield 8.4/10 Very good (772) "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 Oct 26 - Oct 27 [](https://www.expedia.ca/Springfield-Hotels-Candlewood-Suites-West-Springfield.h897535.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/2b026b4b.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/a89bc327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG Pittsfield 9.4/10 Exceptional (55) "Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marti CA $201 CA $224 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/f450d89a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/74865ec0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge Pittsfield 9.0/10 Wonderful (726) "Great stay, perfect " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lawrence CA $130 CA $177 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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) ![Interior entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c3ea2282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/3ef861f5.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 (786) "Nice hotel. Very friendly and professional staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Magen CA $137 CA $153 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.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) ![Room (Firehouse)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property - evening/night](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/4d2e9eec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Main Inn Queen)](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3ac2703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1018) "Picture perfect Inn" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jeff CA $194 CA $280 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/0fe63f9b.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) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.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 (767) "Lovely spot, great accommodations, friendly staff, and great location." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joanne CA $177 CA $217 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7f86e411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/fd39ba7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires Great Barrington 7.6/10 Good (555) "Excellent location, friendly service, clean, comfortable room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $105 CA $117 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.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) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG Great Barrington 8.8/10 Excellent (678) "This motel was easy access right off the highway, super clean, and the staff was great. We would definitely stay here again. Breakfast options were good as well. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tina CA $143 CA $159 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/18100/18056/25c325c5.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) ### La Quinta Inn & Suites by Wyndham Springfield MA Metro Center 8.2/10 Very good (1284) "Love this hotel, 2nd time staying here, family friendly, clean, nice room, great restaurants, convenient location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynne CA $161 CA $182 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.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) ![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) ![Desk, blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/451ff749.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) ### Quality Inn West Springfield West Springfield 7.0/10 Good (1027) "Convenient nice cozy hotel with breakfast included and spacious rooms. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danielle CA $125 CA $143 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/663f69c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed (Dewey Carriage House Inn)](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/468cf971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/7b669948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/f4d43d3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Constance by the Lenox Collection Lenox 8.4/10 Very good (555) "Very quiet and comfortable " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Beth CA $134 CA $150 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Lenox-Hotels-Rookwood-Inn.h4945461.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/c204d876.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) ![Business centre](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c2037034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FairBridge Inn Express Pittsfield 5.4/10 (799) "Good service and people" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerod CA $94 CA $105 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee service](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/9d1d3cb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/775c3761.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/772cf402.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue – A Modern Hotel, an Ascend Collection Hotel West Springfield 9.4/10 Exceptional (57) "Wonderful staff and beautiful new, clean rooms!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori CA $170 CA $195 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.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=2025-11-07&endDate=2025-11-08®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 theater in Chester! [See all hotels in Chester](https://www.expedia.ca/Hotel-Search?startDate=2025-11-07&endDate=2025-11-08&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 Chester, Massachusetts, offers a delightful blend of outdoor adventures and romantic scenery, making it an ideal vacation spot. Visitors can enjoy attractions such as urban parks, nature reserves, and historic houses. For a complete experience, don’t miss the Chester Racecourse, Chester Zoo, and the historic Chester Castle, as well as exploring the charming Chester city itself, perfect for families and adventure seekers alike. [](https://expedia.ca/Chester-Town-Hall-Hotels.0-l553248621532666604-0.Travel-Guide-Filter-Hotels) #### Chester Town Hall Chester Town Hall offers a rich cultural experience, showcasing stunning architecture and vibrant civic life, making it a must-visit for history and culture enthusiasts alike. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532666604) ## More cheap stays in Chester ![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 $137 CA $157 total Nov 2 - Nov 3 includes taxes & fees 6.8/10 (1,014 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 $163 CA $182 total Nov 16 - Nov 17 includes taxes & fees 7/10 Good! (1,012 reviews) [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Suites-Northampton-Amherst.h24588.Hotel-Information) ![Quality Inn West Springfield](https://images.trvl-media.com/lodging/1000000/10000/7500/7486/7f7ace74_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn West Springfield 1150 Riverdale St, West Springfield, MA CA $125 CA $143 total Nov 3 - Nov 4 includes taxes & fees 7/10 Good! (1,019 reviews) [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.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 $170 CA $195 total Nov 23 - Nov 24 includes taxes & fees 9.4/10 Exceptional! (48 reviews) [](https://expedia.ca/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.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, On Route 5, West Springfield, MA CA $112 CA $129 total Nov 24 - Nov 25 includes taxes & fees 5.8/10 (1,010 reviews) [](https://expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-West-SpringfieldRoute-5.h459711.Hotel-Information) ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Howard Johnson by Wyndham Lenox 462 Pittsfield Rd, Routes 7 and 20, Lenox, MA CA $111 CA $123 total Oct 26 - Oct 27 includes taxes & fees 7.4/10 Good! (812 reviews) [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ## Hotels in Chester with star-rating ![4 Star Hotels](https://images.trvl-media.com/lodging/2000000/1460000/1457800/1457797/fdeb3407_w.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/1000000/20000/18100/18056/71c77a60_w.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/1000000/30000/27100/27090/23b7c14f_w.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 ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 5/5 Excellent "Clean room " A verified traveller from Trenton stayed at Berkshire Mountain Lodge Posted 21 hours ago [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![The Ellery](//images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg) ### The Ellery 5/5 Excellent "Rooms clean and comfortable home like feeling " A verified traveller stayed at The Ellery Posted 5 days ago [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Springfield MA](//images.trvl-media.com/lodging/1000000/20000/18100/18056/71c77a60_y.jpg) ### La Quinta Inn & Suites by Wyndham Springfield MA 5/5 Excellent "Bed was very comfortable, and the hotel was delightful." A verified traveller stayed at La Quinta Inn & Suites by Wyndham Springfield MA Posted 5 days ago [](https://expedia.ca/Springfield-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Springfield-MA.h18056.Hotel-Information) ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 5/5 Excellent "In a very nice annex suite." A verified traveller stayed at The Red Lion Inn Posted 6 days ago [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Blue – A Modern Hotel, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2_y.jpg) ### Blue – A Modern Hotel, an Ascend Collection Hotel 5/5 Excellent "Pleasantly surprised. Nice clean and spacious rooms. Comfortable bed and large bathroom. Hotel seemed very new. " A verified traveller stayed at Blue – A Modern Hotel, an Ascend Collection Hotel Posted 6 days ago [](https://expedia.ca/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information) ![Holiday Inn & Suites Pittsfield-Berkshires by IHG](//images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54_y.jpg) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 5/5 Excellent "Enjoyable stay. Staff were very nice. " A verified traveller stayed at Holiday Inn & Suites Pittsfield-Berkshires by IHG Posted 7 days ago [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![D. Hotel Suites & Spa](//images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 5/5 Excellent "We’ve stayed here every fall for the past 3 years, and will continue doing so. Suite is spacious, breakfast is good, employees are kind and respectful. " A verified traveller stayed at D. Hotel Suites & Spa Posted 7 days ago [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 5/5 Excellent "Yes" A verified traveller from Boynton Beach stayed at Berkshires Untold Posted 7 days ago [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 5/5 Excellent "Clean room, nice view" A verified traveller stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel Posted 9 days ago [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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? > [Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"](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. 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 [Glendale Falls](https://www.expedia.ca/Glendale-Falls-Huntington.d553248621532666605.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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)