Title: Hotels in Cheshire, MA - Best Cheshire Hotels from £66 - Fully Refundable Options - Expedia.co.uk [Cheshire Travel Guide](https://expedia.co.uk/Cheshire.dx6005398)[Holiday Rentals in Cheshire](https://expedia.co.uk/Cheshire-Holiday-Rentals.d6005398.Travel-Guide-HolidayRentals)[Flights to Cheshire](https://expedia.co.uk/Cheap-Flights-To-Cheshire.d6005398.Travel-Guide-Flights)[Cheshire Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Cheshire.d6005398.Car-Hire-Guide)[Cheshire Holidays](https://expedia.co.uk/Cheshire.d6005398.Holidays-City-Breaks) ![The road less traveled sometimes is absolutely beautiful. In a month this will be a great spot for Autumn. I will repost the exact same foliage shot and see if I am correct. Excited to do it actually..](https://images.trvl-media.com/place/6005398/5524f182-4aec-4e46-bab1-4eb1dd804bd0.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Ed Gaffny # Find hotels in Cheshire, MA from £66 ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Cheshire Pool [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2025-10-10&d1=2025-10-10&endDate=2025-10-12&d2=2025-10-12&amenities=POOL) Apart­ment [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2025-10-10&d1=2025-10-10&endDate=2025-10-12&d2=2025-10-12&lodging=APARTMENT) Hot tub [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2025-10-10&d1=2025-10-10&endDate=2025-10-12&d2=2025-10-12&amenities=HOT_TUB) Family friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2025-10-10&d1=2025-10-10&endDate=2025-10-12&d2=2025-10-12&travelerType=family_friendly) Pet friendly [](https://www.expedia.co.uk/Hotel-Search?destination=Cheshire%2C+Massachusetts%2C+United+States+of+America®ionId=6005398&latLong=42.562027%2C-73.16288&adults=2&startDate=2025-10-10&d1=2025-10-10&endDate=2025-10-12&d2=2025-10-12&amenities=PETS) ## Check prices for these dates Tonight [26 Sept - 27 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6005398&startDate=2025-09-26&endDate=2025-09-27&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [27 Sept - 28 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6005398&startDate=2025-09-27&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [26 Sept - 28 Sept](https://www.expedia.co.uk/Hotel-Search?regionId=6005398&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [3 Oct - 5 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=6005398&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top 10 Cheshire hotels and places to stay ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/6f32fa47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/ffb7a388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, Private Bathroom (Field of Dreams) | Individually decorated, individually furnished, free WiFi, bed sheets](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/d973dbd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/18000000/17330000/17326600/17326568/8a6408f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Harbour House Inn Cheshire 9.4/10 Exceptional (52) "We had a wonderful stay! Brandi is a wonderful host, super friendly and full of helpful information! The afternoon cookies and morning breakfast were delicious! Will definitely stay again next time we’re in the area!! " £199 includes taxes & fees 7 Oct - 8 Oct [](https://www.expedia.co.uk/Cheshire-Hotels-Harbour-House-Inn.h17326568.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Non Lakeside Superior Room, 2 Queen beds | Premium bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/d3eea453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 (1016) "Great Indian restaurant in the hotel!" £96 includes taxes & fees 27 Oct - 28 Oct [](https://www.expedia.co.uk/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, pool loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f43c89bb.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) ![Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham Lenox 9.0/10 Wonderful (1012) "Nice area to visit " £97 includes taxes & fees 1 Oct - 2 Oct [](https://www.expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/84274eb9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold Lenox 9.0/10 Wonderful (732) "Rooms are a clean and upgraded motel. Nice lobby and rooms. " £106 includes taxes & fees 29 Sept - 30 Sept [](https://www.expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/64adfbe5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining room](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/16150550.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Village in the Berkshires Williamstown 8.6/10 Excellent (2021) "Clean room, friendly staff, affordable." £91 includes taxes & fees 20 Oct - 21 Oct [](https://www.expedia.co.uk/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily full breakfast ](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a5a66acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Queen Bed | Living area | TV](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/d32c867e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 King Bed | 1 bedroom, individually decorated, individually furnished](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/f3a87415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cornell Inn, Lenox & The Berkshires Lenox 9.0/10 Wonderful (1005) "We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect." £136 includes taxes & fees 28 Oct - 29 Oct [](https://www.expedia.co.uk/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/0fe63f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/4f7ca94f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Room, 3 Bedrooms | 1 bedroom, in-room safe, iron/ironing board, free cots/infant beds](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG South Lee 9.0/10 Wonderful (738) "The lodging was convenient to all the area attractions." £115 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Hypo-allergenic bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, open 6:00 AM to 10 PM, pool loungers](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/ecbe7d49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/433bbf3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/3000/2943/a866db4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel Downstreet, an Ascend Collection Hotel North Adams 8.8/10 Excellent (1011) "Property was very clean and view of mountain from window was awesome beds very comfortable and loved the hot tub and pool" £121 includes taxes & fees 26 Oct - 27 Oct [](https://www.expedia.co.uk/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/137f5231.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/2b2e1d76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Tent | 2 bedrooms](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/e9560cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/3f004a6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Huttopia Berkshires Williamstown 10/10 Exceptional (4) "Perfect place for a relaxing getaway! We loved everything! " £82 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information) ![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Check-in/check-out kiosk](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/670699cf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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 (660) "It was a great Stay where we had to it was a good area I would come back to this place again " £95 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite (Main Inn Queen) | 1 bedroom, Frette Italian sheets, hypo-allergenic bedding, desk](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/3ac2703b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room (Firehouse) | 1 bedroom, Frette Italian sheets, hypo-allergenic bedding, desk](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/71ef2331.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds (Main Inn) | 1 bedroom, Frette Italian sheets, hypo-allergenic bedding, desk](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/5f2e6b29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Red Lion Inn Stockbridge 8.8/10 Excellent (1009) "great place have stayed several times, and hope to return." £169 includes taxes & fees 29 Sept - 30 Sept [](https://www.expedia.co.uk/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/a50a3d54.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, desk, laptop workspace, blackout curtains](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/207845f4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/6b95ddf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2100/2067/5acdf3c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn & Suites Pittsfield-Berkshires by IHG Pittsfield 8.0/10 Very good (882) "Our stay was very pleasant " £91 includes taxes & fees 5 Oct - 6 Oct [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Suites-Pittsfield-Berkshires.h2067.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 cots/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) ![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) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG Pittsfield 9.6/10 Exceptional (44) "Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout" £106 includes taxes & fees 2 Oct - 3 Oct [](https://www.expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/663f69c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/f4d43d3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/7b669948.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/5000000/4950000/4945500/4945461/w2880h1917x0y0-550a94f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Constance by the Lenox Collection Lenox 8.4/10 Very good (546) "Staff was so friendly and helpful. The room was small and comfortable and the grounds were well kept. " £125 includes taxes & fees 29 Sept - 30 Sept [](https://www.expedia.co.uk/Lenox-Hotels-Rookwood-Inn.h4945461.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds | Premium bedding, minibar, in-room safe, desk](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/651f878e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/9e766351.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/c3ea2282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hotel On North Pittsfield 9.6/10 Exceptional (774) "Great property! Very large clean room in a unique hotel! " £149 includes taxes & fees 5 Oct - 6 Oct [](https://www.expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.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) ![Reception](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/f6ede23a.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) ![Lobby](https://images.trvl-media.com/lodging/3000000/2760000/2758900/2758858/0c3db9f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Williamstown Motel Williamstown 9.4/10 Exceptional (301) "It was clean and in a convenient location " £105 includes taxes & fees 29 Sept - 30 Sept [](https://www.expedia.co.uk/Williamstown-Hotels-Williamstown-Motel.h2758858.Hotel-Information) ![Front of property – evening/night](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/d48c4129.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/f3e43c7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hallway](https://images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/1ea731f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Williams Inn Williamstown 9.6/10 Exceptional (507) "Great hotel, staff and restaurant!" £201 includes taxes & fees 5 Oct - 6 Oct [](https://www.expedia.co.uk/Williamstown-Hotels-The-Williams-Inn.h35658765.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/8666c376.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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/eac89037.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Berkshire Hills Inn & Suites Pittsfield 8.6/10 Excellent (1012) "Great property would certainly stay again." £95 includes taxes & fees 29 Sept - 30 Sept [](https://www.expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.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) ![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) ![Front of property](https://images.trvl-media.com/lodging/3000000/2840000/2832200/2832172/2c0ca8ed.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) ### The Villager Motel Williamstown 8.8/10 Excellent (742) "Perfect location for our passing through vacay." £75 includes taxes & fees 28 Sept - 29 Sept [](https://www.expedia.co.uk/Williamstown-Hotels-The-Villager-Motel.h2832172.Hotel-Information) ![Suite, 2 Bedrooms | 2 bedrooms, Frette Italian sheets, premium bedding, down duvets](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room (Superior King Bed with a Porch) | 2 bedrooms, Frette Italian sheets, premium bedding, down duvets](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/aaec0515.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/ae684309.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/4417504a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Porches Inn at Mass MoCA North Adams 9.4/10 Exceptional (425) "Great hotel, lovely pool and hot tub. We got upgraded to a suite!" £174 includes taxes & fees 30 Sept - 1 Oct [](https://www.expedia.co.uk/North-Adams-Hotels-The-Porches-Inn.h7662392.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.co.uk/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12®ionId=6005398&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Hotels.d6005398.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FCheshire-Hotels.d6005398.Travel-Guide-Hotels) ## Learn more about Cheshire Get away to romantic Cheshire! Enjoy the skiing, hiking and lake views. [See all hotels in Cheshire](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12&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 ![Best Western Plus Berkshire Hills Inn & Suites](//images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg) ### Best Western Plus Berkshire Hills Inn & Suites 10/10 Excellent "Staff is friendly and accommodating " [](https://expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again. " [](https://expedia.co.uk/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "What a beautiful place. I wish I could have stayed longer. Top notch!" [](https://expedia.co.uk/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "It's just a nice place and the staff is very nice " [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Porches Inn at Mass MoCA](//images.trvl-media.com/lodging/8000000/7670000/7662400/7662392/dcf42e0d_y.jpg) ### The Porches Inn at Mass MoCA 10/10 Excellent "True to its historic character, the attention to detail was splendid! " [](https://expedia.co.uk/North-Adams-Hotels-The-Porches-Inn.h7662392.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Excellent hotel. Great staff. " [](https://expedia.co.uk/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Hotel On North](//images.trvl-media.com/lodging/11000000/10250000/10246200/10246103/bb876934_y.jpg) ### Hotel On North 10/10 Excellent "Great property! Very large clean room in a unique hotel! " [](https://expedia.co.uk/Pittsfield-Hotels-Hotel-On-North.h10246103.Hotel-Information) ![Hotel Downstreet, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/10000/3000/2943/73bb1216_y.jpg) ### Hotel Downstreet, an Ascend Collection Hotel 10/10 Excellent "Totally perfect for mass mocha" [](https://expedia.co.uk/North-Adams-Hotels-Holiday-Inn-Berkshires.h2943.Hotel-Information) ![The Williams Inn](//images.trvl-media.com/lodging/36000000/35660000/35658800/35658765/e381d7f2_y.jpg) ### The Williams Inn 10/10 Excellent "Great hotel. Food and drinks were very good. Not much to do in the town but a great place for walking." [](https://expedia.co.uk/Williamstown-Hotels-The-Williams-Inn.h35658765.Hotel-Information) ## More cheap stays in Cheshire ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Howard Johnson by Wyndham Lenox 462 Pittsfield Rd, Routes 7 and 20, Lenox, MA £66 2 Oct - 3 Oct includes taxes & fees 7.4/10 Good! (802 reviews) [](https://expedia.co.uk/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![FairBridge Inn Express](https://images.trvl-media.com/lodging/1000000/10000/1600/1543/abb5a87f_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### FairBridge Inn Express 16 Cheshire Road, Pittsfield, MA £67 11 Oct - 12 Oct includes taxes & fees 5.2/10 (782 reviews) [](https://expedia.co.uk/Pittsfield-Hotels-Econo-Lodge.h1543.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Yankee, Trademark Collection by Wyndham 461 Pittsfield Rd, Lenox, MA £97 1 Oct - 2 Oct includes taxes & fees 9/10 Wonderful! (1,012 reviews) [](https://expedia.co.uk/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/6acef387_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Best Western Plus Berkshire Hills Inn & Suites 1350 W Housatonic St, Pittsfield, MA £95 29 Sept - 30 Sept includes taxes & fees 8.4/10 Very Good! (1,012 reviews) [](https://expedia.co.uk/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 1055 South Street, Pittsfield, MA £106 2 Oct - 3 Oct includes taxes & fees 9.6/10 Exceptional! (40 reviews) [](https://expedia.co.uk/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/1d74d3f4_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn 170 Housatonic Street, Lee, MA £77 26 Oct - 27 Oct includes taxes & fees 8.2/10 Very Good! (1,006 reviews) [](https://expedia.co.uk/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Cheshire? > The most popular time to visit Cheshire is during the summer months, particularly July and August. At this time, the climate is pleasantly warm, with average temperatures ranging from 17 to 22°C, making it superb for exploring the stunning countryside and charming towns. > > > > During the peak season of June to August, Cheshire comes alive with a variety of outdoor activities and events. Attractions such as the beautiful Tatton Park and the historic Chester Zoo are bustling with families and nature enthusiasts alike. The delightful weather lends itself to leisurely walks along the picturesque canals or through the scenic gardens, allowing you to fully immerse yourself in the region's natural beauty. > > > > For couples seeking romance, these summer months offer vibrant festivals, open-air concerts, and various local events that showcase Cheshire's rich heritage. Imagine indulging in al fresco dining at one of the many quaint bistros, where you can enjoy seasonal dishes made from local produce while soaking up the lively atmosphere. > > > > If you're looking for a slightly quieter experience, consider visiting in September. This month often sees fewer crowds while still enjoying lovely weather and the beautiful autumn colours beginning to emerge. You'll be able to explore the area at a more leisurely pace and perhaps take advantage of some off-peak pricing on accommodations and activities. ### Can I cancel my hotel reservation on Expedia? > You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Cheshire. ### How can I save on a Cheshire hotel booking with Expedia? > Before booking your Cheshire hotel, remember to join Expedia's free travel rewards program. Just sign up and sign in to access our lowest Member Prices as well as members-only perks. You could also enjoy savings by bundling together your hotel and flights on Expedia. ### How much is the nightly rate at a Cheshire hotel? > Prices for hotels in Cheshire often vary, but you can find a great deal from £66 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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[Tanglewood Music Center](https://www.expedia.co.uk/Tanglewood-Music-Center-Lenox.d503292.Attraction) - [Ventfort Hall Mansion and Gilded Age Museum](https://www.expedia.co.uk/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Attraction) - [Williams College](https://www.expedia.co.uk/Williams-College-Williamstown.d6091833.Attraction) - [Visit Williamstown](https://www.expedia.co.uk/Williamstown.dx7859) - [Windsor Holidays](https://www.expedia.co.uk/Windsor.d6005427.Holidays-City-Breaks) - [Car hire Adams](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Adams.d6005393.Car-Hire-Guide) - [Car hire Lee](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lee.d8572.Car-Hire-Guide) - [Car hire Lenox](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Lenox.d8587.Car-Hire-Guide) - [Car hire near Pittsfield State Forest](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Pittsfield-State-Forest.d6339854.Car-Hire-Guide) - [Car hire Pittsfield](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Pittsfield.d9478.Car-Hire-Guide) - 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