Title: 2 Stars Hotels in Cheshire, Massachusetts from CA $98 - Find Cheap Cheshire Hotels With 2 Stars | Expedia.ca [Cheshire Travel Guide](https://expedia.ca/Cheshire.dx6005398)[Hotels in Cheshire](https://expedia.ca/Cheshire-Hotels.d6005398.Travel-Guide-Hotels)[Vacation Rentals in Cheshire](https://expedia.ca/Cheshire-Vacation-Rentals.d6005398.Travel-Guide-VacationRentals)[Flights to Cheshire](https://expedia.ca/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[Cheshire Car Rentals](https://expedia.ca/Car-Rentals-In-Cheshire.d6005398.Car-Rental-Guide)[Cheshire Vacation Packages](https://expedia.ca/Cheshire.d6005398.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ed Gaffny # 2 Stars Hotels in Cheshire, Massachusetts from CA $98 ![](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 availability on Cheshire 2 Star Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-14&endDate=2025-10-15&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-15&endDate=2025-10-16&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6005398&startDate=2025-10-24&endDate=2025-10-26&adults=2&star=20&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cheshire 2 Star Hotels ![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) ![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) ### Howard Johnson by Wyndham Lenox Lenox 7.6/10 Good (809) "Good for the one night drive through! " CA $111 CA $124 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.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) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/bd64a090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/3ed5d9ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fitness facility](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/c204d876.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### FairBridge Inn Express Pittsfield 5.4/10 (794) "Good service and people" CA $95 CA $106 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Pittsfield-Hotels-Econo-Lodge.h1543.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) ![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) ![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) ### The Yankee, Trademark Collection by Wyndham Lenox 9.0/10 Wonderful (1008) "Good breakfast King rooms are the best facing the mountains Recently remodeled " CA $188 CA $210 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/90dd9d88.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 (1013) "Good breakfast; pleasant staff on duty 24/7; convenient location." CA $143 CA $159 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Lobby sitting area](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/67e1adab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/2b026b4b.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) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG Pittsfield 9.4/10 Exceptional (53) "Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout" CA $167 CA $187 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/9aabb83a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/b5e2455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Lee 8.4/10 Very good (1009) "Staff was very helpful - easy location - clean rooms!" CA $130 CA $145 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/b4275c3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/300000/297200/297173/c07737f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Inn Pittsfield 7.8/10 Good (830) "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" CA $104 CA $117 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Inn.h297173.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/f5e7ded9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/18aac20b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/ddd4b2e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Mountain view](https://images.trvl-media.com/lodging/2000000/1500000/1498700/1498642/15afb24f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Williamstown Williamstown 6.6/10 (888) "Great affordable place to stay while in the northern Berkshires." CA $154 CA $172 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Williamstown-Hotels-Howard-Johnson-By-Wyndham-Williamstown.h1498642.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/3e2c75da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 8:00 AM to 10:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/ceca8706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Bed, Non-Smoking, Accessible | View from room](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/5d049cdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites Berkshires-Lenox Lenox 9.2/10 Wonderful (1003) "Very clean, nice amenities , great location!!" CA $156 CA $174 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5d49dcf2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/be737544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/5e45920f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35100000/35099400/35099355/dd484194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Williamstown Williamstown 8.8/10 Excellent (385) "our stay was great." CA $201 CA $224 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Fairfield-Inn-Suites-By-Marriott-Williamstown.h35099355.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/3e40d6cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/0c3db9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/8e0c73d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/7720f0f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Williamstown Motel Williamstown 9.4/10 Exceptional (304) "Was upgraded to a larger room for no special reason. Very nice proprietor. For budget priced accommodations, this is an excellent value. Would definitely stay here again if I am in the area." CA $109 CA $122 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/45e111cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/568a1b81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/6203d3bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/488c62c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Villager Motel Williamstown 8.8/10 Excellent (748) "Perfect location for our passing through vacay." CA $111 CA $124 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-The-Villager-Motel.h2832172.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/a5e72142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/4a1f06eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/7549d558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, cribs/infant beds, free WiFi](https://images.trvl-media.com/lodging/2000000/1760000/1753400/1753359/75e29869.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Willows Motel Williamstown Williamstown 9.0/10 Wonderful (961) "Good breakfast; comfortable beds; smiling service; great tv; very accomodating" CA $125 CA $139 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Williamstown-Hotels-Willows-Motel-Williamstown.h1753359.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/caece0b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/af22be9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Double Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/53d12ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4600000/4595900/4595809/44727a40.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cozy Corner Motel Williamstown 9.2/10 Wonderful (874) "Very nice staff, nice breakfast" CA $105 CA $124 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Williamstown-Hotels-Cozy-Corner-Motel.h4595809.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/126ab2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/bf0ac5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/beaa7d9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1800000/1793600/1793522/4d496801.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Travel Lodge Austerlitz 5.4/10 (452) "Clean comfortable. Good for the price. " CA $95 CA $106 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Albany-Hotels-Berkshire-Travel-Lodge.h1793522.Hotel-Information) ![Courtyard](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/69831a98.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed, Patio | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/d7f7feed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Honeymoon Suite, 1 King Bed, Patio | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/5e670f07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 3 Bedrooms, Mountainside | Living area](https://images.trvl-media.com/lodging/96000000/95130000/95124600/95124564/2f0dc604_edited_9c5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Springs Motel New Ashford 9.2/10 Wonderful (78) "The Springs Motel was a delight! Something away from the boring, staple type of hotel. The staff was so friendly and welcoming. The coffee and breakfast is a great touch! Can't wait to go back" CA $142 CA $156 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/New-Ashford-Hotels-The-Springs-Motel.h95124564.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) ![Standard Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/920000/913100/913013/b0a99b9c.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) ### Econo Lodge Lee - Great Barrington Lee 6.4/10 (637) "Easy check in" CA $88 CA $98 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Lee-Hotels-Econo-Lodge-Lee-Great-Barrington.h913013.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/f0d9797c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/8337d62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Queen](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/fbf7e370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/fa802938.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whitlock Lenox 8.6/10 Excellent (272) "We were disappointed in the shabby quality of this venue. But the bathroom had been remodeled. Older hotels can be an adventure and this one was," CA $175 CA $195 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/b03b8d67.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/997bd7c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/25529e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/50000000/49180000/49177800/49177721/d7e3ccf3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pilgrim Inn Lee 5.8/10 (328) "There was not anyone in the office when we checked in. We had to call a number to get instructions on how to program our key cards for our room." CA $103 CA $116 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Lee-Hotels-Pilgrim-Inn.h49177721.Hotel-Information) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/ed652faf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/67356bb4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/ba469908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Miscellaneous](https://images.trvl-media.com/lodging/19000000/18680000/18670300/18670223/d7cd7f22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 1896 House Country Inn & Motels Williamstown 6.6/10 (446) "Interesting cosy room, lovely seats on verandah, easy walk across bridge to Inn, easy tea and coffee maker." CA $132 CA $148 total includes taxes & fees Nov 12 - Nov 13 [](https://www.expedia.ca/Williamstown-Hotels-1896-House-Country-Inn-Motels.h18670223.Hotel-Information) ![](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%2F2Star-Cheshire-Hotels.s20-0-d6005398.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F2Star-Cheshire-Hotels.s20-0-d6005398.Travel-Guide-Filter-Hotels) ## Explore similar 3-star hotels Many 3-star hotels have the same amenities as 2-star hotels. See all 3-star hotels in Cheshire. ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Berkshire Mountain Lodge 8 Dan Fox Dr, Pittsfield, MA CA $131 CA $177 total Nov 2 - Nov 3 includes taxes & fees 8.8/10 Excellent! (698 reviews) [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Vacation Village in the Berkshires 276 Brodie Mountain Rd, Williamstown, MA CA $129 CA $159 total Nov 2 - Nov 3 includes taxes & fees 8.6/10 Excellent! (2,057 reviews) [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hotel Downstreet, an Ascend Collection Hotel 40 Main St, North Adams, MA CA $182 CA $203 total Nov 12 - Nov 13 includes taxes & fees 8.6/10 Excellent! (1,003 reviews) [](https://expedia.ca/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) Still don't see what you're looking for? [See all properties in Cheshire.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=6005398&star=20) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=6005398&star=20&star=20&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=6005398&star=20&star=20&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=6005398&star=20&star=20&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=6005398&star=20&star=20&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=15%2F10%2F2025&endDate=16%2F10%2F2025®ionId=6005398&star=20&star=20&amenities=WATER_PARK) 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. ## Learn more about Cheshire Get away to romantic Cheshire! Enjoy the skiing, hiking, and natural setting. [See all hotels in Cheshire](https://www.expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29&adults=2®ionId=6005398) ![](https://mediaim.expedia.com/destination/2/03b3e41380b5e881ce17dedb6946d4ac.jpg?impolicy=fcrop&w=899&h=675&p=1&q=high) Photo by Ed Gaffny ## Top Cheshire Hotel Reviews ![Howard Johnson by Wyndham Lenox](//images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg) ### Howard Johnson by Wyndham Lenox 10/10 Excellent "Good for the one night drive through! " [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ## Find out more about Cheshire Want to get out of town on the cheap? Thanks to the low rates and great discounts at the top 2 Stars hotels in Cheshire, Cheshire you can sneak away on the trip of your dreams with plenty of cash to spare. In addition to the friendly staff and well-maintained surroundings, you’ll find comfortable rooms, complimentary bath products, and quiet sleeping areas, so you can kick back with all the basic conveniences after a long day. Plus, these properties are perfect, if you need a jumping-off point for exploring the local attractions. Several of the best hotels with 2 Stars in Cheshire are situated just a stone’s throw from both public transportation and the city’s main freeways. Use the travel tools at Expedia.ca to search for options near your favorite neighborhood, find a cheap deal, and book your room. You won’t believe how inexpensive your next vacation can be when you settle in at a top two star hotel in Cheshire. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [2 Star Hotels in East Village Historic District](https://www.expedia.ca/2Star-East-Village-Historic-District-Amherst-Hotels.s20-n553248621557920008-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in South End](https://www.expedia.ca/2Star-South-End-Springfield-Hotels.s20-n898868902485037056-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Franklin](https://www.expedia.ca/3Star-Franklin-Hotels.s30-0-d601800.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Otis](https://www.expedia.ca/3Star-Otis-Hotels.s30-0-d6005412.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Stockbridge](https://www.expedia.ca/3Star-Stockbridge-Hotels.s30-0-d162575.Travel-Guide-Filter-Hotels) - [3 Star Hotels in The Berkshires](https://www.expedia.ca/3Star-The-Berkshires-Hotels.s30-0-d6047665.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Wellesley](https://www.expedia.ca/3Star-Wellesley-Hotels.s30-0-d7665.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Hudson](https://www.expedia.ca/4Star-Hudson-Hotels.s40-0-d6025353.Travel-Guide-Filter-Hotels) - [4 Star Hotels in North Adams](https://www.expedia.ca/4Star-North-Adams-Hotels.s40-0-d9137.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Phillipston](https://www.expedia.ca/4Star-Phillipston-Hotels.s40-0-d3000441438.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Shirley](https://www.expedia.ca/4Star-Shirley-Hotels.s40-0-d6131820.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Sudbury](https://www.expedia.ca/4Star-Sudbury-Hotels.s40-0-d9770.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Uxbridge](https://www.expedia.ca/4Star-Uxbridge-Hotels.s40-0-d168855.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Paxton](https://www.expedia.ca/5Star-Paxton-Hotels.s50-0-d3000441398.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sudbury](https://www.expedia.ca/5Star-Sudbury-Hotels.s50-0-d9770.Travel-Guide-Filter-Hotels) - [5 Star Hotels in Sutton](https://www.expedia.ca/5Star-Sutton-Hotels.s50-0-d183346.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Berkshires](https://www.expedia.ca/5Star-The-Berkshires-Hotels.s50-0-d6047665.Travel-Guide-Filter-Hotels) - [Farmstay in Adams](https://www.expedia.ca/Adams-Agritourism.d6005393-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Adams](https://www.expedia.ca/Adams-Apart-Hotels.d6005393-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Adams](https://www.expedia.ca/Adams-Bed-And-Breakfast.d6005393-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Adams](https://www.expedia.ca/Adams-Chalets.d6005393-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Adams](https://www.expedia.ca/Adams-Guest-Houses.d6005393-aaGuestHouses.Travel-Guide-Accommodation) - [Beach Hotel Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Beach-Hotel.0-0-d6005393-tBeachHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Cheap-Hotels.0-0-d6005393-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Historic-Hotel.0-0-d6005393-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Mountain-Hotels.0-0-d6005393-tMountainHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Adams](https://www.expedia.ca/Adams-Hotels-Spa-Hotel.0-0-d6005393-tSpaHotel.Travel-Guide-Filter-Hotels) - [Adams Hotels](https://www.expedia.ca/Adams-Hotels.d6005393.Travel-Guide-Hotels) - [Inns in Adams](https://www.expedia.ca/Adams-Inns.d6005393-aaInns.Travel-Guide-Accommodation) - [Lodges in Adams](https://www.expedia.ca/Adams-Lodges.d6005393-aaLodges.Travel-Guide-Accommodation) - [Resorts in Adams](https://www.expedia.ca/Adams-Resort-Hotels.d6005393-aaResortHotels.Travel-Guide-Accommodation) - [Aparthotels in Dalton](https://www.expedia.ca/Dalton-Apart-Hotels.d6911-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Dalton](https://www.expedia.ca/Dalton-Bed-And-Breakfast.d6911-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cheap Hotels in Dalton](https://www.expedia.ca/Dalton-Hotels-Cheap-Hotels.0-0-d6911-tCheapHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Dalton](https://www.expedia.ca/Dalton-Hotels-Family-Hotel.0-0-d6911-tFamilyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Dalton](https://www.expedia.ca/Dalton-Hotels-Spa-Hotel.0-0-d6911-tSpaHotel.Travel-Guide-Filter-Hotels) - [Dalton Hotels](https://www.expedia.ca/Dalton-Hotels.d6911.Travel-Guide-Hotels) - [Lodges in Dalton](https://www.expedia.ca/Dalton-Lodges.d6911-aaLodges.Travel-Guide-Accommodation) - [Motels in Dalton](https://www.expedia.ca/Dalton-Motels.d6911-aaMotels.Travel-Guide-Accommodation) - [Farmstay in Hancock](https://www.expedia.ca/Hancock-Agritourism.d112303-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Hancock](https://www.expedia.ca/Hancock-Apart-Hotels.d112303-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Hancock](https://www.expedia.ca/Hancock-Bed-And-Breakfast.d112303-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Condo Rentals in Hancock](https://www.expedia.ca/Hancock-Condos.d112303-aaCondos.Travel-Guide-Accommodation) - [Guest Houses in Hancock](https://www.expedia.ca/Hancock-Guest-Houses.d112303-aaGuestHouses.Travel-Guide-Accommodation) - [Boutique Hotels in Hancock](https://www.expedia.ca/Hancock-Hotels-Boutique-Hotel.0-0-d112303-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Hancock](https://www.expedia.ca/Hancock-Hotels-Cheap-Hotels.0-0-d112303-tCheapHotels.Travel-Guide-Filter-Hotels) - [Historic Hotels in Hancock](https://www.expedia.ca/Hancock-Hotels-Historic-Hotel.0-0-d112303-tHistoricHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Hancock](https://www.expedia.ca/Hancock-Hotels-Luxury-Hotel.0-0-d112303-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mountain Hotels in Hancock](https://www.expedia.ca/Hancock-Hotels-Mountain-Hotels.0-0-d112303-tMountainHotels.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Hancock](https://www.expedia.ca/Hancock-Hotels-Pet-Friendly-Hotel.0-0-d112303-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Hancock](https://www.expedia.ca/Hancock-Hotels-Spa-Hotel.0-0-d112303-tSpaHotel.Travel-Guide-Filter-Hotels) - [Hancock Hotels](https://www.expedia.ca/Hancock-Hotels.d112303.Travel-Guide-Hotels) - [Inns in Hancock](https://www.expedia.ca/Hancock-Inns.d112303-aaInns.Travel-Guide-Accommodation) - [Resorts in Hancock](https://www.expedia.ca/Hancock-Resort-Hotels.d112303-aaResortHotels.Travel-Guide-Accommodation) - [Hotels near Jiminy Peak Mountain Resort](https://www.expedia.ca/Jiminy-Peak-Mountain-Resort-Hotels.0-l553248621532665536-0.Travel-Guide-Filter-Hotels) - [Guest Houses in Lanesborough](https://www.expedia.ca/Lanesborough-Guest-Houses.d6005408-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Lanesborough](https://www.expedia.ca/Lanesborough-Hotels-Cheap-Hotels.0-0-d6005408-tCheapHotels.Travel-Guide-Filter-Hotels) - [Spa Hotels in Lanesborough](https://www.expedia.ca/Lanesborough-Hotels-Spa-Hotel.0-0-d6005408-tSpaHotel.Travel-Guide-Filter-Hotels) - [Lanesborough Hotels](https://www.expedia.ca/Lanesborough-Hotels.d6005408.Travel-Guide-Hotels) - [Inns in Lanesborough](https://www.expedia.ca/Lanesborough-Inns.d6005408-aaInns.Travel-Guide-Accommodation) - [Vacation Homes in Lanesborough](https://www.expedia.ca/Lanesborough-Private-Vacation-Homes.d6005408-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Hotels near Mount Greylock](https://www.expedia.ca/Mount-Greylock-Hotels.0-l6091829-0.Travel-Guide-Filter-Hotels) - [Hotels near Mount Greylock State Reservation Visitor Center](https://www.expedia.ca/Mount-Greylock-State-Reservation-Visitor-Center-Hotels.0-l6272782-0.Travel-Guide-Filter-Hotels) - [Aparthotels in New Ashford](https://www.expedia.ca/New-Ashford-Apart-Hotels.d183333-aaApartHotels.Travel-Guide-Accommodation) - [B&B in New Ashford](https://www.expedia.ca/New-Ashford-Bed-And-Breakfast.d183333-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Luxury Hotels in New Ashford](https://www.expedia.ca/New-Ashford-Hotels-Luxury-Hotel.0-0-d183333-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [New Ashford Hotels](https://www.expedia.ca/New-Ashford-Hotels.d183333.Travel-Guide-Hotels) - [Inns in New Ashford](https://www.expedia.ca/New-Ashford-Inns.d183333-aaInns.Travel-Guide-Accommodation) - [Villas in New Ashford](https://www.expedia.ca/New-Ashford-Villas.d183333-aaVillas.Travel-Guide-Accommodation) - [Farmstay in Savoy](https://www.expedia.ca/Savoy-Agritourism.d6005417-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Savoy](https://www.expedia.ca/Savoy-Apart-Hotels.d6005417-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Savoy](https://www.expedia.ca/Savoy-Bed-And-Breakfast.d6005417-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Savoy](https://www.expedia.ca/Savoy-Cabins.d6005417-aaCabins.Travel-Guide-Accommodation) - [Chalets in Savoy](https://www.expedia.ca/Savoy-Chalets.d6005417-aaChalets.Travel-Guide-Accommodation) - [Condo Resorts in Savoy](https://www.expedia.ca/Savoy-Condominium-Resort.d6005417-aaCondominiumResort.Travel-Guide-Accommodation) - [Cottages in Savoy](https://www.expedia.ca/Savoy-Cottages.d6005417-aaCottages.Travel-Guide-Accommodation) - [Cheap Hotels in Savoy](https://www.expedia.ca/Savoy-Hotels-Cheap-Hotels.0-0-d6005417-tCheapHotels.Travel-Guide-Filter-Hotels) - [Savoy Hotels](https://www.expedia.ca/Savoy-Hotels.d6005417.Travel-Guide-Hotels) - [Inns in Savoy](https://www.expedia.ca/Savoy-Inns.d6005417-aaInns.Travel-Guide-Accommodation) - [Motels in Savoy](https://www.expedia.ca/Savoy-Motels.d6005417-aaMotels.Travel-Guide-Accommodation) - [Resorts in Savoy](https://www.expedia.ca/Savoy-Resort-Hotels.d6005417-aaResortHotels.Travel-Guide-Accommodation) - [Farmstay in Windsor](https://www.expedia.ca/Windsor-Agritourism.d6005427-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Windsor](https://www.expedia.ca/Windsor-Apart-Hotels.d6005427-aaApartHotels.Travel-Guide-Accommodation) - [B&B in Windsor](https://www.expedia.ca/Windsor-Bed-And-Breakfast.d6005427-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Windsor](https://www.expedia.ca/Windsor-Castles.d6005427-aaCastles.Travel-Guide-Accommodation) - [Chalets in Windsor](https://www.expedia.ca/Windsor-Chalets.d6005427-aaChalets.Travel-Guide-Accommodation) - [Guest Houses in Windsor](https://www.expedia.ca/Windsor-Guest-Houses.d6005427-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Windsor](https://www.expedia.ca/Windsor-Hotels-Cheap-Hotels.0-0-d6005427-tCheapHotels.Travel-Guide-Filter-Hotels) - [Windsor Hotels](https://www.expedia.ca/Windsor-Hotels.d6005427.Travel-Guide-Hotels) - [Inns in Windsor](https://www.expedia.ca/Windsor-Inns.d6005427-aaInns.Travel-Guide-Accommodation) - [Lodges in Windsor](https://www.expedia.ca/Windsor-Lodges.d6005427-aaLodges.Travel-Guide-Accommodation) - [Motels in Windsor](https://www.expedia.ca/Windsor-Motels.d6005427-aaMotels.Travel-Guide-Accommodation) - [Resorts in Windsor](https://www.expedia.ca/Windsor-Resort-Hotels.d6005427-aaResortHotels.Travel-Guide-Accommodation) - [Flights to Windsor](https://www.expedia.ca/Cheap-Flights-To-Windsor.d6005427.Travel-Guide-Flights) - [Flights from Adams](https://www.expedia.ca/lp/flights/6005393/flights-from-adams) - [Flights from Windsor](https://www.expedia.ca/lp/flights/6005427/flights-from-windsor) - [Adams Vacations](https://www.expedia.ca/Adams.d6005393.Destination-Travel-Guides) - [Car rental Hancock](https://www.expedia.ca/Car-Rentals-In-Hancock.d112303.Car-Rental-Guide) - [Car rentals near Jiminy Peak Mountain Resort](https://www.expedia.ca/Car-Rentals-In-Jiminy-Peak-Mountain-Resort.d553248621532665536.Car-Rental-Guide) - [Dalton Vacation Rentals](https://www.expedia.ca/Dalton-Vacation-Rentals.d6911.Travel-Guide-VacationRentals) - [Book 2 Star Hotels in Cheshire on Expedia.com](https://www.expedia.com/2Star-Cheshire-Hotels.s20-0-d6005398.Travel-Guide-Filter-Hotels)