Title: Chester Motel: Browse Cheap Motels in Chester 2025 | Expedia.ca [Hotels in Chester](https://expedia.ca/Chester-Hotels.d6005399.Travel-Guide-Hotels)[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) ![](https://mediaim.expedia.com/destination/2/5376b74ed08fb0cd0348035ae5ca74c9.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Elizabeth Massa Peroulakis # Search Motels in Chester from CA $91 - ![](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 ## Check prices for these dates Next weekend [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=MOTEL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Motels ![Room, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/83dd2b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel Great Barrington 9.0/10 Wonderful (782) "This was an older property, but room was nice and bathroom was updated. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Martha [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.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) ![Reception](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/fd39ba7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking](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 (556) "I loved the stay people were nice loved the pool and internet was great " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer CA $106 CA $118 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/5a6f7f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox Lenox 7.6/10 Good (818) "Staff was very friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $111 CA $124 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.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) ![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) ![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) ![Exterior](https://images.trvl-media.com/lodging/108000000/107580000/107579600/107579521/a50fdd34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### River Valley Inn West Hatfield 8.6/10 Excellent (90) "Room was very clean. Owners are great Close to all things in Deerfield Would definitely stay there again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kenneth CA $168 CA $187 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/c3ce1b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b4275c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/3a99baa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/8f954601.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Inn Pittsfield 7.8/10 Good (837) "This property has a mid century motel look from the street but the rooms have been recently upgraded and are fully modern inside. A great value and comfortable place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Phillip CA $104 CA $117 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/75f1ed66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/1ddc8409.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed | View from room](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/6d6cf248.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1740000/1730200/1730144/aca96762.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wagon Wheel Inn Lenox 7.0/10 Good (640) "There was a mouse in our room at night." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brin CA $97 CA $109 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Lenox-Hotels-Wagon-Wheel-Inn.h1730144.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/2558ee66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/cdf64ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/9b821fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pleasant Valley Motel West Stockbridge West Stockbridge 6.8/10 (1001) "good average place to stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry CA $82 CA $91 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/219cd416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/d1430bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/483e190d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn Lee 7.6/10 Good (409) "Room was clean, bed comfortable, nearby to restaurants, gas stations. Only one complaint and that is that the room/bathroom was small and felted cramped and slightly difficult to move around, other than that drawback it served it’s purpose " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kimberly CA $121 CA $135 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) ![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/aaa7fba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/36b54e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/c97f0de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion Great Barrington 8.6/10 Excellent (543) "The check-in was easy and the room was ready and clean. It was nice having our dogs with us. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $178 CA $199 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/0fb6095c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/e4a88a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/f0e5252a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, rollaway beds](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/f9deb77e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Econo Lodge Lee - Great Barrington Lee 6.4/10 (644) "Staff friendly, room was quiet, large and comfortable. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara CA $83 CA $92 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/5b50a276.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Double Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/1fb406bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | Terrace/patio](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/26677985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family House | Private kitchen](https://images.trvl-media.com/lodging/28000000/27070000/27064300/27064222/062df4a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Becket Motel Becket 6.8/10 (60) "A very basic motel with a good size refrigerator. You can't cook here (microwave, a sink but no kitchen towels, grills outside but not sure whose those are). A continental breakfast is listed but is not available . Perhaps the owners should update this. No stuff around. The door was opened remotely. The best thing was its proximity to the Jacob's Pillow Dance Center. If you only want to place to sleep this is adequate. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Diane CA $126 CA $189 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Becket-Hotels-Becket-Motel.h27064222.Hotel-Information) ![Premium Apartment | Private kitchen](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/61ae6bd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/fbd2cba0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Apartment | Living area](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/75dbf9d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102810000/102807000/102806911/22135a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### East Rock Inn Great Barrington 9.4/10 Exceptional (35) "Quiet and peaceful location set off the road, with woodsy area in the back. Very close to Main Street shops and restaurants. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amanda CA $198 CA $222 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Great-Barrington-Hotels-East-Rock-Inn.h102806911.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459800/459711/28e65efc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/1000000/460000/459800/459711/1480a8e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverdale Inn West Springfield 5.8/10 (999) "Place is neglected. Clearly no effort or money is spent on cleaning. Place smells like it is dirty. Low cost, and looks and smells like it." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dave CA $109 CA $125 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-West-SpringfieldRoute-5.h459711.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) ![Business centre](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c2037034.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) ### FairBridge Inn Express Pittsfield 5.4/10 (807) "Room spotless and staff helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $95 CA $106 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.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=2025-11-21&endDate=2025-11-22®ionId=6005399&adults=2&lodging=MOTEL&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-Motels.d6005399-aaMotels.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Motels.d6005399-aaMotels.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ![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 10/10 Excellent "Yes" [](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 10/10 Excellent "I love the ambience - historic and comfortable and excellent food. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Perfect Stay in the Berkshire This hotel was spacious, clean, and had everything needed for a comfortable stay. The room was well-maintained, and the location was ideal—close to local attractions and easy to get around. Smooth check-in process and great access throughout. Highly recommend! " [](https://expedia.ca/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![D. Hotel Suites & Spa](//images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "Amazingly helpful front desk staff; clean, updated, quiet room with beautiful light and comfy bed; on-site restaurant with a diverse array of menu options; hot tub; good walking at adjacent country club, and short drive to Northampton. Everything you could possibly want/need...love this place! " [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Quality Inn West Springfield](//images.trvl-media.com/lodging/1000000/10000/7500/7486/7f7ace74_y.jpg) ### Quality Inn West Springfield 10/10 Excellent "Breakfast " [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Great staff and the room was awesome!! Would definitely come again!" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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 10/10 Excellent "Spotless and friendly staff" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean, convenience, great staff, quiet, beautiful and secluded yet close to everything! Thank you" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Courtyard by Marriott West Springfield](//images.trvl-media.com/lodging/34000000/33300000/33298700/33298677/90293a2b_y.jpg) ### Courtyard by Marriott West Springfield 10/10 Excellent "." [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ## Find out more about Chester ## Chester Motels information | Number of reviews | 8,214 | | --- | --- | | Accommodation | 19 Motels | | Lowest Price | CA $91 | | Highest Price | CA $222 | ## Frequently asked questions ### What can I expect from a motel trip to Chester? > If you're having a hard time finding motels in Chester, let Expedia help you find a motel or something similar from over 845 lodging options in the larger area. Just use our search tools to filter by price per night or cost-saving amenities such as free parking and free airport transportation. ### What is a motel? > When you stay at a motel, you'll often find an outdoor pool and free parking. With a stay at a motel, you'll usually access your room directly from the parking lot. Starting in the early 1950s, customized neon signs often lit up the roadside motels, and you can see these today along the historic U.S. Route 66. ### What are the best motels in Chester? > These are some of our customers' favorite motels to book in the larger area. [Riverdale Inn](https://www.expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-West-SpringfieldRoute-5.h459711.Hotel-Information) is located 20.2 mi (32.5 km) from the heart of Chester. Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. [FairBridge Inn Express](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information): Free WiFi and free parking are available during your stay, along with room amenities like a microwave. Central Chester is 17.4 mi (28 km) away. [Howard Johnson by Wyndham Lenox](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information): Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Located 17 mi (27.3 km) from the heart of Chester. [Monument Mountain Motel](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information): Central Chester is 19.5 mi (31.4 km) away. Free WiFi and free parking are available during your stay, along with room amenities like free wired internet. [River Valley Inn](https://www.expedia.ca/West-Hatfield-Hotels-Hatfield-Inn.h107579521.Hotel-Information): 18.6 mi (29.9 km) from the heart of Chester. Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. ### What can I do in Chester? > Some outdoorsy places nearby include Glendale Falls, Pyramid Lake, and Otis Reservoir. You'll find these family-friendly sights in the area: The Bookstore, Congregation Beth Israel, and Bousquet Ski Area. While you're checking out the area, consider visiting Chester Town Hall, Jacob's Pillow, and Otis Ridge. ### What's the weather like in Chester? > Weather can make or break a roadtrip, so here's some data about year-round temperatures in Chester to help you plan yours: 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. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall. ### What are my options for getting around Chester when staying in a motel? > We've gathered some information about getting around Chester to help you navigate your stay: Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the city center. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. 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