Title: Browse the Best Chester Resorts from CA $103 | 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 Resort Hotels in Chester from CA $103 - ![](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 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=6005399&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chester Resorts No exact matches found, but these alternatives could be just right ## Recommended hotels in Chester ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/eac89037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/8666c376.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites Pittsfield 8.6/10 Excellent (1000) "I have stayed here many times and it is consistently a comfortable, clean and quiet place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeanine CA $92 CA $103 total includes taxes & fees Dec 4 - Dec 5 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 (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) ![Lobby](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/02a266b2.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) ![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) ![Coffee service](https://images.trvl-media.com/lodging/1000000/30000/27900/27815/9d1d3cb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Blue – A Modern Hotel, an Ascend Collection Hotel West Springfield 9.6/10 Exceptional (92) "Great staff super nice beautiful hotel lots of parking " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Yovelys CA $141 CA $162 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/West-Springfield-Hotels-Blue-A-Modern-Hotel.h27815.Hotel-Information) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/f80f24a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5754h3835x5y5-e38781aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Non Smoking, Kitchen (with Sofabed, Full Kitchen) | Private kitchenette](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/w5753h3840x5y0-8e399dec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking, Kitchen (Larger Room, Sofabed, Full Kitchen)](https://images.trvl-media.com/lodging/1000000/20000/15800/15705/b5bac949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baldwin Inn & Suites, SureStay Collection by Best Western West Springfield 7.6/10 Good (99) "Clean room, friendly staff, good mattress. Not fancy or plush, but perfect for a one or two night place to land while attending events at the Big E. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kim CA $142 CA $162 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Springfield-Hotels-Regency-Inn-Suites.h15705.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/2bcbba21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, down comforters, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/f36d24b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/40e8ece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/23000000/22420000/22413500/22413458/08190a34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tru by Hilton Chicopee Springfield Chicopee 8.8/10 Excellent (1000) "Nice place and clean i recommend it. " ![Mexico](https://a.travel-assets.com/egds/marks/flags/mx.svg) Jessly CA $122 CA $138 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Springfield-Hotels-Tru-By-Hilton-Chicopee-Springfield.h22413458.Hotel-Information) ![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/2000000/1080000/1076200/1076188/83dd2b57.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) ![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/44ab9667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel Great Barrington 9.0/10 Wonderful (791) "Yes it was clean & staff was very polite. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara L. [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.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) ![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) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.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) ![Room, 2 Queen Beds, Refrigerator](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/04ad8e9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/cde7c3e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/w3838h2587x1y0-b516eca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast](https://images.trvl-media.com/lodging/3000000/2080000/2076200/2076197/w3839h2584x0y3-17f28d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Westfield Westfield 8.4/10 Very good (811) "Very pet friendly and the night check in agent was super kind and friendly" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) olivia townsend CA $151 CA $168 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-By-Hilton-Westfield.h2076197.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) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/b005a67f.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) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/8974a65a.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) ![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) ![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) ![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) ### Travelodge by Wyndham Great Barrington Berkshires Great Barrington 7.6/10 Good (559) "The staff were very friendly and accommodating " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tom CA $105 CA $117 total includes taxes & fees Nov 23 - Nov 24 [](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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.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) ### Howard Johnson by Wyndham Lenox Lenox 7.6/10 Good (824) "Staff was very friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $107 CA $120 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.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) ![Non Lakeside Superior Room, 2 Queen beds](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.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) ### 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/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/5fd0e723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires Lenox 9.8/10 Exceptional (11) "New hotel very nice" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) joel CA $189 CA $211 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1220000/1217900/1217805/bcd941e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1220000/1217900/1217805/b2e75c4f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Bed, Non-Smoking](https://images.trvl-media.com/lodging/2000000/1220000/1217900/1217805/069efa95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1220000/1217900/1217805/3908ae38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Hadley-Amherst Area Hadley 9.0/10 Wonderful (953) "Nice hotel, friendly helpful staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tim CA $167 CA $186 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Springfield-Hotels-Hampton-Inn-Hadley-Amherst-Area.h1217805.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 (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) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/6d13ff43.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) ![Gazebo](https://images.trvl-media.com/lodging/1000000/900000/897600/897535/1d1dace5.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) ![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) ![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) ![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 (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) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/219cd416.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deep soaking bathtub](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/14870b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn Lee 7.6/10 Good (410) "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 $113 CA $127 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.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) ![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/a89bc327.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) 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&lodging=HOTEL_RESORT&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-Resort-Hotels.d6005399-aaResortHotels.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChester-Resort-Hotels.d6005399-aaResortHotels.Travel-Guide-Accommodation) ## Top Chester Hotel Reviews ### Homewood Suites by Hilton Hadley Amherst 10/10 Excellent "Clean room, spacious room, nice staff, and good location for our trip. " [](https://expedia.ca/Springfield-Hotels-Homewood-Suites-By-Hilton-Hadley-Amherst.h33232831.Hotel-Information) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG 10/10 Excellent "Everything was amazing my bf did get a beer at the bar that was expired but everything else was amazing " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.Hotel-Information) ### Quality Inn West Springfield 10/10 Excellent "Very courteous staff. Comfortable, clean room. Always interesting people travelling through." [](https://expedia.ca/Springfield-Hotels-Quality-Inn-West-Springfield.h7486.Hotel-Information) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Great stay!" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ### Berkshire Mountain Lodge 10/10 Excellent "The suites were large. Nice to have separate bedroom. Kitchen with all the basics. Perfect for a getaway " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ### Courtyard by Marriott West Springfield 10/10 Excellent "Work trip meet my needs" [](https://expedia.ca/Springfield-Hotels-Courtyard-By-Marriott-West-Springfield.h33298677.Hotel-Information) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 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! " [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ### The Ellery 10/10 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!" [](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information) ### Quality Inn Westfield - Springfield 10/10 Excellent "Staff was very friendly. Everything was clean and well kept. Small hotel but very cozy and quiet." [](https://expedia.ca/Springfield-Hotels-Quality-Inn-Westfield-Springfield.h1118896.Hotel-Information) ## Find out more about Chester ## Chester Resorts information | Number of reviews | 14,128 | | --- | --- | | Accommodation | 4 Resorts | | Lowest Price | CA $103 | | Highest Price | CA $211 | ## Frequently asked questions ### What is Chester like for a resort vacation? > You deserve to get away, and a resort is the ideal place to find all the amenities and services you need for a relaxing stay in Chester. One of the comfortable resorts in the area might be just what you're looking for, whether you're hoping for great restaurants on site, a state-of-the-art fitness center, or activities for the kids. ### What's the best resort for my stay in Chester? > Our top-rated resort near Chester: [Holiday Inn Club Vacations Oak 'n Spruce Resort](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h13232379.Hotel-Information) - Ski resort. 15 mi (24.1 km) from Chester. Has a sauna, a fitness center, and a terrace. ### What can I do in Chester? > Experience the local theater scene at Chester Town Hall, or bring the kids to Ashintully Gardens for some family fun. In the area, other attractions include Littleville Lake and Pyramid Lake. ### What's the 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. The snowiest months in Chester are January, February, November, and March, with each month seeing an average of 6 inches of snowfall. ### What's the best way to get to and around Chester? > Fly into Westfield, MA (BAF-Barnes Municipal), which is located 15.4 mi (24.7 km) from the heart of the city. You can also search for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 18.9 mi (30.4 km) away. If you'd like to venture out around the area, you may want to rent a car for your trip. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in Otis](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - [B&B in Becket](https://www.expedia.ca/Becket-Bed-And-Breakfast.d6005395-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Becket](https://www.expedia.ca/Becket-Chalets.d6005395-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Becket](https://www.expedia.ca/Becket-Guest-Houses.d6005395-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Becket](https://www.expedia.ca/Becket-Hotels-Cheap-Hotels.0-0-d6005395-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Becket](https://www.expedia.ca/Becket-Hotels-Luxury-Hotel.0-0-d6005395-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Becket](https://www.expedia.ca/Becket-Hotels-Mountain-Hotels.0-0-d6005395-tMountainHotels.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Becket](https://www.expedia.ca/Becket-Hotels-Romantic-Hotel.0-0-d6005395-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Becket Hotels](https://www.expedia.ca/Becket-Hotels.d6005395.Travel-Guide-Hotels) - [Motels in Becket](https://www.expedia.ca/Becket-Motels.d6005395-aaMotels.Travel-Guide-Accommodation) - [B&B in Blandford](https://www.expedia.ca/Blandford-Bed-And-Breakfast.d80625-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Blandford](https://www.expedia.ca/Blandford-Hotels-Cheap-Hotels.0-0-d80625-tCheapHotels.Travel-Guide-Filter-Hotels) - [Blandford Hotels](https://www.expedia.ca/Blandford-Hotels.d80625.Travel-Guide-Hotels) - [Inns in Blandford](https://www.expedia.ca/Blandford-Inns.d80625-aaInns.Travel-Guide-Accommodation) - [Motels in Blandford](https://www.expedia.ca/Blandford-Motels.d80625-aaMotels.Travel-Guide-Accommodation) - [Hotels with a Pool in Chesterfield](https://www.expedia.ca/Chesterfield-Hotels-Hotel-With-Pool.0-0-d89029-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Chesterfield](https://www.expedia.ca/Chesterfield-Hotels-Pet-Friendly-Hotel.0-0-d89029-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Chesterfield Hotels](https://www.expedia.ca/Chesterfield-Hotels.d89029.Travel-Guide-Hotels) - [Apartments in Huntington](https://www.expedia.ca/Huntington-Apartments.d6005407-aaApartments.Travel-Guide-Accommodation) - [B&B in Huntington](https://www.expedia.ca/Huntington-Bed-And-Breakfast.d6005407-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Huntington](https://www.expedia.ca/Huntington-Castles.d6005407-aaCastles.Travel-Guide-Accommodation) - [Chalets in Huntington](https://www.expedia.ca/Huntington-Chalets.d6005407-aaChalets.Travel-Guide-Accommodation) - [Spa Hotels in Huntington](https://www.expedia.ca/Huntington-Hotels-Spa-Hotel.0-0-d6005407-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Huntington](https://www.expedia.ca/Huntington-Hotels-Waterpark-Hotels.0-0-d6005407-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Huntington Hotels](https://www.expedia.ca/Huntington-Hotels.d6005407.Travel-Guide-Hotels) - [Inns in Huntington](https://www.expedia.ca/Huntington-Inns.d6005407-aaInns.Travel-Guide-Accommodation) - [Motels in Huntington](https://www.expedia.ca/Huntington-Motels.d6005407-aaMotels.Travel-Guide-Accommodation) - [Hotels near Jacob's Pillow](https://www.expedia.ca/Jacobs-Pillow-Hotels.0-l553248621532666599-0.Travel-Guide-Filter-Hotels) - [Middlefield Hotels](https://www.expedia.ca/Middlefield-Hotels.d132966.Travel-Guide-Hotels) - [Inns in Middlefield](https://www.expedia.ca/Middlefield-Inns.d132966-aaInns.Travel-Guide-Accommodation) - [B&B in Norwich Lake](https://www.expedia.ca/Norwich-Lake-Bed-And-Breakfast.d553248635975876005-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Farmstay in Otis](https://www.expedia.ca/Otis-Agritourism.d6005412-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Otis](https://www.expedia.ca/Otis-Apart-Hotels.d6005412-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Otis](https://www.expedia.ca/Otis-Bed-And-Breakfast.d6005412-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Otis](https://www.expedia.ca/Otis-Chalets.d6005412-aaChalets.Travel-Guide-Accommodation) - [Condo Rentals in Otis](https://www.expedia.ca/Otis-Condos.d6005412-aaCondos.Travel-Guide-Accommodation) - [Guest Houses in Otis](https://www.expedia.ca/Otis-Guest-Houses.d6005412-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Otis](https://www.expedia.ca/Otis-Hotels-Cheap-Hotels.0-0-d6005412-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Otis](https://www.expedia.ca/Otis-Hotels-Luxury-Hotel.0-0-d6005412-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Otis Hotels](https://www.expedia.ca/Otis-Hotels.d6005412.Travel-Guide-Hotels) - [Inns in Otis](https://www.expedia.ca/Otis-Inns.d6005412-aaInns.Travel-Guide-Accommodation) - [Motels in Otis](https://www.expedia.ca/Otis-Motels.d6005412-aaMotels.Travel-Guide-Accommodation) - [Rv Parks in Otis](https://www.expedia.ca/Otis-RV-Parks.d6005412-aaRVParks.Travel-Guide-Accommodation) - [Hotels near Otis Reservoir](https://www.expedia.ca/Otis-Reservoir-Hotels.0-l553248621532666595-0.Travel-Guide-Filter-Hotels) - [Resorts in Otis](https://www.expedia.ca/Otis-Resort-Hotels.d6005412-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Otis Ridge](https://www.expedia.ca/Otis-Ridge-Hotels.0-l553248621532666596-0.Travel-Guide-Filter-Hotels) - [B&B in Russell](https://www.expedia.ca/Russell-Bed-And-Breakfast.d6005415-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Russell](https://www.expedia.ca/Russell-Cabins.d6005415-aaCabins.Travel-Guide-Accommodation) - [Cheap Hotels in Russell](https://www.expedia.ca/Russell-Hotels-Cheap-Hotels.0-0-d6005415-tCheapHotels.Travel-Guide-Filter-Hotels) - [Russell Hotels](https://www.expedia.ca/Russell-Hotels.d6005415.Travel-Guide-Hotels) - [Inns in Russell](https://www.expedia.ca/Russell-Inns.d6005415-aaInns.Travel-Guide-Accommodation) - [Hotels & Resorts for Couples in Sherwood Forest](https://www.expedia.ca/Sherwood-Forest-Becket-Hotels-Couples-Resorts-Hotels.0-n553248635976472129-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Sherwood Forest](https://www.expedia.ca/Sherwood-Forest-Becket-Hotels-Mountain-Hotels.0-n553248635976472129-0-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Sherwood Forest](https://www.expedia.ca/Sherwood-Forest-Becket-Hotels-Pet-Friendly-Hotel.0-n553248635976472129-0-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Sherwood Forest](https://www.expedia.ca/Sherwood-Forest-Becket-Hotels-Spa-Hotel.0-n553248635976472129-0-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Washington](https://www.expedia.ca/Washington-Hotels-Hotel-With-Pool.0-0-d553248634998690770-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Washington](https://www.expedia.ca/Washington-Hotels-Luxury-Hotel.0-0-d553248634998690770-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Washington Hotels](https://www.expedia.ca/Washington-Hotels.d553248634998690770.Travel-Guide-Hotels) - [Adults Only Resorts & in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Adults-Only-Resorts.0-0-d6234063-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Beach-Hotel.0-0-d6234063-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Boutique-Hotel.0-0-d6234063-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Cheap-Hotels.0-0-d6234063-tCheapHotels.Travel-Guide-Filter-Hotels) - [Golf Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Golf-Hotel.0-0-d6234063-tGolfHotel.Travel-Guide-Filter-Hotels) - [Historic Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Historic-Hotel.0-0-d6234063-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Hotel-With-Pool.0-0-d6234063-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with a Lazy River in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Hotels-With-A-Lazy-River.0-0-d6234063-tHotelswithaLazyRiver.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Hotels-With-Hot-Tubs.0-0-d6234063-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Hotels-With-Indoor-Pool.0-0-d6234063-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Hotels with Kitchenettes in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Hotels-With-Kitchenettes.0-0-d6234063-tHotelswithKitchenettes.Travel-Guide-Filter-Hotels) - [Hotels with Tennis Courts in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Hotels-With-Tennis-Courts.0-0-d6234063-tHotelswithTennisCourts.Travel-Guide-Filter-Hotels) - [Hotels with Waterslides in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Hotels-With-Waterslides.0-0-d6234063-tHotelswithWaterslides.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Luxury-Hotel.0-0-d6234063-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Oceanfront Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Oceanfront-Hotels.0-0-d6234063-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Pet-Friendly-Hotel.0-0-d6234063-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Romantic Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Romantic-Hotel.0-0-d6234063-tRomanticHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Spa-Hotel.0-0-d6234063-tSpaHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Waterpark-Hotels.0-0-d6234063-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Hotel Wedding Venues Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Wedding-Hotels.0-0-d6234063-tWeddingHotels.Travel-Guide-Filter-Hotels) - [Winery Hotels in Western Massachusetts](https://www.expedia.ca/Western-Massachusetts-Hotels-Winery-Hotel.0-0-d6234063-tWineryHotel.Travel-Guide-Filter-Hotels) - [Western Massachusetts Hotels](https://www.expedia.ca/Western-Massachusetts-Hotels.d6234063.Travel-Guide-Hotels) - [B&B in Worthington](https://www.expedia.ca/Worthington-Bed-And-Breakfast.d6005428-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Boutique Hotels in Worthington](https://www.expedia.ca/Worthington-Hotels-Boutique-Hotel.0-0-d6005428-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Worthington Hotels](https://www.expedia.ca/Worthington-Hotels.d6005428.Travel-Guide-Hotels) - [Resorts in Worthington](https://www.expedia.ca/Worthington-Resort-Hotels.d6005428-aaResortHotels.Travel-Guide-Accommodation) - [Flights to Russell](https://www.expedia.ca/Cheap-Flights-To-Russell.d6005415.Travel-Guide-Flights) - [Flights to Western Massachusetts](https://www.expedia.ca/Cheap-Flights-To-Western-Massachusetts.d6234063.Travel-Guide-Flights) - [Flights from Otis](https://www.expedia.ca/lp/flights/6005412/flights-from-otis) - [Flights from Russell](https://www.expedia.ca/lp/flights/6005415/flights-from-russell) - [Flights from Western Massachusetts](https://www.expedia.ca/lp/flights/6234063/flights-from-western-massachusetts) - [Becket Land Trust Historic Quarry](https://www.expedia.ca/Becket-Land-Trust-Historic-Quarry-Becket.d553248621532666600.Vacation-Attraction) - [Otis Vacations](https://www.expedia.ca/Otis.d6005412.Destination-Travel-Guides) - [Western Massachusetts Vacations](https://www.expedia.ca/Western-Massachusetts.d6234063.Destination-Travel-Guides) - [Visit Western Massachusetts](https://www.expedia.ca/Western-Massachusetts.dx6234063) - [Car rental Chesterfield](https://www.expedia.ca/Car-Rentals-In-Chesterfield.d89029.Car-Rental-Guide) - [Car rentals near Western Massachusetts](https://www.expedia.ca/Car-Rentals-In-Western-Massachusetts.d6234063.Car-Rental-Guide) - [Hertz Rental Cars in Western Massachusetts](https://www.expedia.ca/Hertz-Car-Rentals-In-Western-Massachusetts.d6234063-c40.Car-Rental-Guide-Suppliers) - [Hiper Rent a Car Rental Cars in Western Massachusetts](https://www.expedia.ca/Hiper-Rent-A-Car-Car-Rentals-In-Western-Massachusetts.d6234063-c1026.Car-Rental-Guide-Suppliers) - [Owners Rental Cars in Western Massachusetts](https://www.expedia.ca/Owners-Car-Rentals-In-Western-Massachusetts.d6234063-c1066.Car-Rental-Guide-Suppliers) - [Rent A Wreck Rental Cars in Western Massachusetts](https://www.expedia.ca/Rent-A-Wreck-Car-Rentals-In-Western-Massachusetts.d6234063-c33.Car-Rental-Guide-Suppliers) - [Western Massachusetts Vacation Rentals](https://www.expedia.ca/Western-Massachusetts-Vacation-Rentals.d6234063.Travel-Guide-VacationRentals) - [Book Resorts in Chester on Expedia.com](https://www.expedia.com/Chester-Resorts.d6005399-aaResorts.Travel-Guide-Accommodation)