Title: Book The Best Hotels in Sheffield, MA for 2026 from CA $116 - Fully Refundable Options - Expedia.ca [Vacation Rentals in Sheffield](https://expedia.ca/Sheffield-Vacation-Rentals.d157238.Travel-Guide-VacationRentals)[Flights to Sheffield](https://expedia.ca/Cheap-Flights-To-Sheffield.d157238.Travel-Guide-Flights)[Sheffield Car Rentals](https://expedia.ca/Car-Rentals-In-Sheffield.d157238.Car-Rental-Guide)[Sheffield Vacation Packages](https://expedia.ca/Sheffield.d157238.Destination-Travel-Guides) ![FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Sheffield, MA from CA $116 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Go beyond your typical stay in Sheffield Pool [](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&amenities=POOL) Spa [](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&amenities=SPA_ON_SITE) Pet friendly [](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&amenities=PETS) Hot tub [](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&amenities=HOT_TUB) Cabin [](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&lodging=CABIN) Family friendly [](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&travelerType=family_friendly) Cottage [](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&lodging=COTTAGE) Apart­ment [](https://www.expedia.ca/Hotel-Search?destination=Sheffield%2C+Massachusetts%2C+United+States+of+America®ionId=157238&latLong=42.109989%2C-73.355141&adults=2&startDate=2026-01-16&d1=2026-01-16&endDate=2026-01-18&d2=2026-01-18&lodging=APARTMENT) ## Check prices for these dates Tonight [Jan 2 - Jan 3](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-01-02&endDate=2026-01-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 3 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-01-03&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sheffield hotels ![Wilder House Berkshires Room 3](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f0c223e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![45-inch flat-screen TV with digital channels, streaming services](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/683afd1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/7fea6163.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f8f74b93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wilder House Berkshires [](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) Sheffield 9.8/10 Exceptional (41) "The rooms are clean and comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Allison Traveling with family CA $235 CA $263 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/c9940794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pines Duplex Suite | View from room](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/7bcf94fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior entrance](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/0fed38f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/18000000/17100000/17094100/17094013/ca0080b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Silver Maple Farm [](https://www.expedia.ca/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.Hotel-Information) East Chatham 9.8/10 Exceptional (98) "Great stay, comfortable place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) barry CA $177 CA $198 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/East-Chatham-Hotels-Inn-At-Silver-Maple-Farm.h17094013.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) ![Egyptian cotton sheets, premium bedding, free WiFi, bed sheets](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/0a525567.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) ![Lounge](https://images.trvl-media.com/lodging/67000000/66250000/66244800/66244754/8337d62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Whitlock [](https://www.expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.Hotel-Information) Lenox 8.6/10 Excellent (282) "The bed was very comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah Traveling with partner CA $134 CA $150 total includes taxes & fees Jan 5 - Jan 6 [](https://www.expedia.ca/Lenox-Hotels-The-Whitlock.h66244754.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](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/d32c867e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/a02c1cad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cornell Inn, Lenox & The Berkshires [](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) Lenox 9.0/10 Wonderful (1001) "Cute property and our room was perfect." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dadri Traveling for leisure CA $197 CA $226 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/7b953453.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Porch](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/d4fc7cd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/21cb26fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Suite, 1 Bedroom, Private Bathroom, Lake View | Living area](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/b4a4e013.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lakehouse Inn [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.Hotel-Information) Lee 9.6/10 Exceptional (290) "Very clean and well presented rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Natalie CA $237 CA $279 total includes taxes & fees Jan 16 - Jan 17 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.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) ![Exterior](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/9b4c64ee.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) ![Lobby](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/967b0257.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshires Untold [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) Lenox 9.0/10 Wonderful (825) "The hotel room was comfortable and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Autumn Traveling solo CA $174 CA $194 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/bb8fdf64.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fire Spa Suite | Room amenity](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/af4baaa3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fire Spa Suite](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/de897732.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039621/3d2d74c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chambery Inn [](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.Hotel-Information) Lee 9.6/10 Exceptional (374) "The room was gorgeous, spacious, and very comfortable." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Samuel Traveling with partner CA $235 CA $262 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Lee-Hotels-Chambery-Inn.h1039621.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) ![Miscellaneous](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.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) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) Lee 9.0/10 Wonderful (1003) "Our room was as described and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dorothy Traveling with partner CA $142 CA $159 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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) ![Grand Villa, 3 Bedrooms](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/5aedd4f2.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) ![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) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) South Lee 9.0/10 Wonderful (813) "Nice spacious room, friendly and accommodating staff, great amenities" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Zina Traveling for leisure CA $131 CA $173 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/8e50ee57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, Private Bathroom (Rockwell - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/4d5a91f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Apartment, Private Bathroom (Greylock - No Pets)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/9aba043f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Garden - Pets Allowed) | Miscellaneous](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/c68ae4d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Shaker Mill Inn [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) West Stockbridge 9.6/10 Exceptional (440) "Very cute and clean room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen Traveling for leisure CA $139 CA $153 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) Lenox 7.6/10 Good (828) "Two very comfortable Queen Size Beds and a nice bathtub with great water pressure in shower!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Melissa Traveling for leisure CA $108 CA $121 total includes taxes & fees Jan 6 - Jan 7 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ebf28595.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/aaa7fba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/36b54e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Little Lion [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) Great Barrington 8.6/10 Excellent (548) "2- my wife and I had a nice big bed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David Traveling with family CA $151 CA $169 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) Great Barrington 9.0/10 Wonderful (811) "Rooms have been recently renovated and were clean and spotless" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hans Traveling solo [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/62ab3ea3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) Great Barrington 8.8/10 Excellent (714) "The hotel was decent overall — clean, comfortable, and well-kept." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sudhendu Traveling with family CA $134 CA $150 total includes taxes & fees Jan 25 - Jan 26 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Fireplace](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/4ea5ab50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![View from room](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3a8723ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1005) "Friendly staff, very clean room and super comfy bed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Linda Traveling with partner CA $139 CA $155 total includes taxes & fees Jan 11 - Jan 12 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Loft, Private Bathroom (Skylight Loft)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/48ea2807.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Private Bathroom (Tanglewood Suite)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/c348a91f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/86910798.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Victorian Room)](https://images.trvl-media.com/lodging/2000000/1200000/1196200/1196186/49947e81.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Brook Farm Inn [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.Hotel-Information) Lenox 9.4/10 Exceptional (164) "Comfortable, quiet, convenient location, very friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan [](https://www.expedia.ca/Lenox-Hotels-Brook-Farm-Inn.h1196186.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) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/e55e7242.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 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) Lenox 9.2/10 Wonderful (1001) "Staff was great, they kept the place clean, the elevator broke and they had it fixed quickly!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) albert Traveling for leisure CA $150 CA $168 total includes taxes & fees Jan 4 - Jan 5 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.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) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/483e190d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/049cb490.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Blackout drapes, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/4000000/3030000/3025500/3025486/d1430bde.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) Lee 7.6/10 Good (411) "Great location convenient to everything in the Berkshires, not far from the highway." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Catherine CA $123 CA $138 total includes taxes & fees Jan 3 - Jan 4 [](https://www.expedia.ca/Lee-Hotels-Sunset-Inn.h3025486.Hotel-Information) ![Luxury Room, 1 King Bed, Bathtub](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/b3e61239.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Flat-screen TV](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/4037455f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/cfdb82a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20040000/20033800/20033760/c5994ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 33 Main [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information) Lenox 10/10 Exceptional (74) "Breakfast was delicious and served in beautiful rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patricia Traveling with partner CA $529 CA $591 total includes taxes & fees Jan 12 - Jan 13 [](https://www.expedia.ca/Lenox-Hotels-33-Main.h20033760.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/6897a130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/9b7b4cbf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Queen Beds (Main Inn)](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 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) Stockbridge 8.8/10 Excellent (1003) "Loved it right down to the soap in the bathroom!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela Traveling for leisure CA $193 CA $277 total includes taxes & fees Jan 14 - Jan 15 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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=2026-01-16&endDate=2026-01-17®ionId=157238&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Hotels.d157238.Travel-Guide-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Hotels.d157238.Travel-Guide-Hotels) ## Learn more about Sheffield Tucked in the Berkshires, this charming town offers scenic hikes at Bartholomew's Cobble and local art at the Sheffield Historical Society. Catch live performances at the Berkshire Theatre Festival in nearby Stockbridge or sample farm-fresh produce at the weekend farmers' market on the town green. [See all hotels in Sheffield](https://www.expedia.ca/Hotel-Search?startDate=2026-01-16&endDate=2026-01-17&adults=2®ionId=157238) ![FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=900&h=600&p=1&q=high) ### Stay near popular Sheffield attractions [](https://expedia.ca/Magnolia-Bluffs-Casino-Hotels.0-l553248621532644877-0.Travel-Guide-Filter-Hotels) #### Magnolia Bluffs Casino Why not roll the dice with a visit to Magnolia Bluffs Casino during your travels in Sheffield? Discover the area's breweries or seek out the hiking trails. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532644877) [](https://expedia.ca/Ashley-House-Hotels.0-l553248621532664810-0.Travel-Guide-Filter-Hotels) #### Ashley House You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532664810) ## More cheap stays in Sheffield ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Quality Inn 372 Main Street Great Barrington MA CA $104 CA $116 total Jan 27 - Jan 28 includes taxes & fees 8.4/10 Very Good! (1,001 reviews) [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Howard Johnson by Wyndham Lenox](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Howard Johnson by Wyndham Lenox 462 Pittsfield Rd Lenox MA CA $108 CA $121 total Jan 6 - Jan 7 includes taxes & fees 7.4/10 Good! (827 reviews) [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.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 CA $113 CA $126 total Feb 1 - Feb 2 includes taxes & fees 8.2/10 Very Good! (1,002 reviews) [](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 415 Stockbridge Rd Great Barrington MA CA $134 CA $150 total Jan 25 - Jan 26 includes taxes & fees 8.8/10 Excellent! (711 reviews) [](https://expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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 CA $139 CA $155 total Jan 11 - Jan 12 includes taxes & fees 9/10 Wonderful! (1,004 reviews) [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Monument Mountain Motel](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/fa93cb94_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Monument Mountain Motel 247 Stockbridge Rd Great Barrington MA [Get rates](https://expedia.ca/Hotel-Search?startDate=16%2F01%2F2026&endDate=17%2F01%2F2026&selected=1076188&PinnedHotelID=1076188&HadPinnedHotel=true®ionId=157238) 8.8/10 Excellent! (810 reviews) [](https://expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ## Hotels in Sheffield with star-rating ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 13 properties [](https://expedia.ca/4Star-Sheffield-Hotels.s40-0-d157238.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 120 properties [](https://expedia.ca/3Star-Sheffield-Hotels.s30-0-d157238.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 103 properties [](https://expedia.ca/2Star-Sheffield-Hotels.s20-0-d157238.Travel-Guide-Filter-Hotels) ## Find out more about Sheffield ### Top reasons to visit Sheffield - **Outdoor Adventure:** Sheffield is a haven for outdoor enthusiasts, offering skiing, hiking, and eco-friendly experiences amidst stunning natural beauty. - **Picturesque Landscapes:** Nestled in the Berkshires, Sheffield boasts breathtaking scenery, ideal for relaxation and exploration. - **Charming Accommodations:** From quaint bed & breakfasts to unique agritourism stays, visitors can find a perfect place to rest. - **Historical Exploration:** The town's rich history invites visitors to discover its cultural heritage and charming architecture. - **Welcoming Atmosphere:** Sheffield offers a warm, friendly vibe, making it a peaceful getaway with low crowds. ### Find great hotels near Sheffield Sheffield, Massachusetts, offers a charming selection of accommodations perfect for every traveller. From inviting bed & breakfasts to unique agritourism properties, you’ll find options that cater to families, adventurers, and pet owners alike. Whether you're seeking luxury hotels or cozy lodgings, Sheffield's hospitality scene promises an unforgettable stay amidst its scenic beauty and vibrant community. - **[Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG: ](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)** Embrace the charm of the Berkshires at this inviting 3.5-star resort, perfect for families, business travellers, and those seeking an LGBTQIA-friendly atmosphere. Located 19.3km from Sheffield, the resort features a range of amenities tailored to both leisure and work. Families can enjoy the mini-golf, shared playground, and arcade game room, while business guests have access to a fully equipped business centre. With its welcoming environment and recreational activities, this resort is a delightful blend of relaxation and productivity. - **[Quality Inn: ](https://www.expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)** For the adventurous spirit, Quality Inn is the ideal choice, situated 9.7km from Sheffield. This hotel caters to those who appreciate both business convenience and outdoor thrills. Guests can easily access nearby skiing, hiking, and snowshoeing, making it perfect for action-packed getaways. The property offers essential business amenities, ensuring that work commitments are met while adventure awaits just outside the door. With its focus on recreation and comfort, Quality Inn is a fantastic option for active travellers. - **[Holiday Inn Express Hotel & Suites Great Barrington by IHG: ](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information)** Just 11.3km from Sheffield, this hotel welcomes guests with its modern, LGBTQIA-friendly environment and business-focused amenities. Ideal for corporate travellers, it features a 24-hour business centre, meeting rooms, and conference space. Guests appreciate the contemporary accommodations and thoughtful services, making it a convenient base for both work and leisure. With its friendly atmosphere and comfortable lodging, Holiday Inn Express is perfect for those who value both productivity and relaxation. ### Where to stay near Sheffield Sheffield, Massachusetts, offers a delightful blend of adventure and relaxation for Canadian travellers. Nestled in the picturesque Berkshires, this charming town is perfect for skiing and outdoor sports, while its historical vibes invite exploration. Nearby areas boast stunning scenery, family-friendly activities, and a warm, welcoming atmosphere. With low crowds and fresh air, Sheffield is an ideal destination for those seeking a peaceful getaway, complete with lovely campgrounds and friendly people to enhance your experience. - **[Great Barrington: ](https://www.expedia.ca/Great-Barrington-Hotels.d110336.Travel-Guide-Hotels)** Located 9.7km from Sheffield, Great Barrington is a vibrant city that attracts visitors year-round, with a notable peak from June to August. This area is a haven for outdoor enthusiasts, offering thrilling skiing and adventure sports. The local ski resorts provide excellent facilities for both beginners and seasoned skiers. Beyond winter sports, visitors can enjoy breathtaking views at nearby lakes and mountains, as well as explore the scenic landscapes of the national state park. Great Barrington’s charm lies in its rich mix of outdoor activities and tranquil nature. - **[The Berkshires: ](https://www.expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels)** Just 17.7km from Sheffield, The Berkshires is renowned for its stunning natural beauty and outdoor adventures. While visitor numbers peak during the summer months, the area remains a popular escape throughout the year. The Berkshires is famous for its ski fields and resorts, making it a hotspot for winter sports enthusiasts. The picturesque landscapes include serene lakes and majestic mountains, perfect for hiking, biking, or simply soaking in the scenery. Additionally, The Berkshires offers a lively cultural scene with various events and conferences, making it a versatile destination. - **[Ashley Falls: ](https://www.expedia.ca/Ashley-Falls-Hotels.d901768766462177280.Travel-Guide-Hotels)** Situated only 6.4km from Sheffield, Ashley Falls is a charming city that sees a moderate flow of visitors, particularly from July to August and in October. This area is ideal for those seeking adventure, with excellent skiing opportunities available at local resorts. The presence of beautiful lakes and parks enhances the outdoor experience, providing spaces for relaxation and recreation. Ashley Falls combines small-town charm with access to exhilarating sports, making it a delightful stop for any traveler looking for both action and tranquility. ### Things to do near Sheffield Sheffield, Massachusetts, offers a variety of activities for adventure and sports enthusiasts, making it ideal for a ski vacation. Visitors can enjoy skiing at local resorts, explore various attractions, and relax at wellness retreats. Additionally, Sheffield features a golf club and meeting rooms for those looking to combine recreation with business. With its picturesque landscapes and numerous outdoor options, Sheffield promises an exciting getaway for all. **Shopping** In Sheffield, enjoy unique finds at the local shops. If you're up for a drive, visit [Lee Premium Outlets](https://www.expedia.ca/Lee-Premium-Outlets-Hotels.0-l6127084-0.Travel-Guide-Filter-Hotels), located 22.5km away, for a variety of brand-name discounts. Also, check out the [Berkshire Mountain Country Store](https://www.expedia.ca/Berkshire-Mountain-Country-Store-Hotels.0-l553248621532665264-0.Travel-Guide-Filter-Hotels) and [Hoffman's Pottery](https://www.expedia.ca/Hoffmans-Pottery-Hotels.0-l553248621532665251-0.Travel-Guide-Filter-Hotels), both 24.1km away, for charming gifts. **Recreation** [Lake Mansfield Park](https://www.expedia.ca/Lake-Mansfield-Park-Hotels.0-l553248621560926695-0.Travel-Guide-Filter-Hotels) offers a tranquil setting for relaxation and leisurely strolls amidst nature. [Music Mountain](https://www.expedia.ca/Music-Mountain-Hotels.0-l553248621561735303-0.Travel-Guide-Filter-Hotels) provides an entertaining atmosphere with live concerts, perfect for enjoying vibrant performances. [Greenock Country Club](https://www.expedia.ca/Greenock-Country-Club-Hotels.0-l553248621560926703-0.Travel-Guide-Filter-Hotels) invites you to embrace the outdoors with golf, surrounded by beautiful landscapes and fresh air. **Adventure** Experience the thrill of skiing at [Ski Butternut](https://www.expedia.ca/Ski-Butternut-Hotels.0-l6182072-0.Travel-Guide-Filter-Hotels), located 8.0km from Sheffield, where the slopes cater to all skill levels. For a scenic hike, explore [Housatonic River Walk](https://www.expedia.ca/Housatonic-River-Walk-Hotels.0-l553248621532665241-0.Travel-Guide-Filter-Hotels), 9.7km away, offering captivating outdoor vistas. Don't miss the excitement of ziplining at [Catamount Aerial Adventure Park](https://www.expedia.ca/Catamount-Aerial-Adventure-Park-Hotels.0-l553248621532664791-0.Travel-Guide-Filter-Hotels), 12.9km from Sheffield. **Nightlife** Experience the vibrant nightlife in Sheffield by visiting the [Mahaiwe Performing Arts Center](https://www.expedia.ca/Mahaiwe-Performing-Arts-Center-Hotels.0-l553248621532665242-0.Travel-Guide-Filter-Hotels) for a captivating show, or enjoy a delightful evening at [Infinity Music Hall and Bistro](https://www.expedia.ca/Infinity-Music-Hall-And-Bistro-Hotels.0-l553248621532664806-0.Travel-Guide-Filter-Hotels), where culture and romance blend perfectly. Don't miss the [Berkshire Theatre Festival](https://www.expedia.ca/Berkshire-Theatre-Festival-Hotels.0-l553248621532665249-0.Travel-Guide-Filter-Hotels) for more entertaining performances, all within a short drive. \*Distances are measured in a straight line; actual driving distances may vary depending on the route. ### Booking tips and Expedia advantages for Sheffield To save money on your trip to Sheffield, Massachusetts, consider visiting during the off-peak months of January and March to April when accommodation prices are lower. Tuesdays are the most affordable days to stay, while Saturdays tend to be pricier. Use Expedia to find tailored deals by filtering for Eco-certified hotels and sorting prices from lowest to highest. Additionally, combining your hotel, flights, and activities into a package can lead to significant savings. Take advantage of free local attractions and consider walking for cost-effective transportation around the charming town. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay in Sheffield are January and March to April, where the prices are slightly lower. This is in comparison to July to August and October, where prices are slightly higher. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay in Sheffield is Tuesday. The most expensive day to stay in Sheffield is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia’s search tool to customize your travel preferences, such as your budget, desired location, and the type of accommodation you prefer. For instance, selecting the Eco-certified filter will showcase sustainable and environmentally-friendly hotels currently available. To find the best prices and offers, simply arrange the price filter from lowest to highest. - **Consider bundling your trip:** You can save money by combining your hotel stay in Sheffield with your flights and activities through an Expedia package. ### Find the best attractions near Sheffield Sheffield, Massachusetts, is an ideal destination for outdoor enthusiasts and adventure seekers, offering a range of activities from skiing to eco-friendly experiences. Visitors can explore beautiful state parks, nature reserves, and serene lakes, making it a perfect spot for sports vacations and connecting with nature. Whether you're looking for thrilling adventures or peaceful retreats, Sheffield provides a diverse array of attractions that cater to every type of traveler. - **[Taconic State Park: ](https://www.expedia.ca/Taconic-State-Park-Hotels.0-l553248621532664790-0.Travel-Guide-Filter-Hotels)** Located 12.9km from Sheffield, this park is a haven for adventure seekers and nature lovers. Explore scenic trails, enjoy hiking, and immerse yourself in the vibrant outdoor atmosphere. - **[Housatonic River: ](https://www.expedia.ca/Housatonic-River-Hotels.0-l682155708745285632-0.Travel-Guide-Filter-Hotels)** A mere 9.7km away, the Housatonic River offers stunning views and a serene environment. Perfect for canoeing and fishing, it invites visitors to relish the tranquility of nature. - **[Umpachene Falls Park: ](https://www.expedia.ca/Umpachene-Falls-Park-Hotels.0-l553248621560926710-0.Travel-Guide-Filter-Hotels)** Just 6.4km from Sheffield, this picturesque waterfall park is ideal for a romantic getaway or an adventurous day out. Enjoy hiking trails and breathtaking views of cascading water. ### Best time to go to Sheffield The best time to visit Sheffield is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly cloudy with light rain. | **![calendar](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | ---------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------- | ---------------------------------------------------------------------------------------------------------------------------- | -------------------------------------------------------------------------------------------------------------- | ------------------------------------------------------------------------------------------------------------- | | January | 23.2°F (-4.9°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | February | 24.8°F (-4.0°C) | Light Rain | Mostly Cloudy | Slightly Low | Average | | March | 32.5°F (0.3°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | April | 44.2°F (6.8°C) | Light Rain | Mostly Cloudy | Average | Slightly Low | | May | 55.9°F (13.3°C) | Light Rain | Mostly Sunny | Average | Average | | June | 63.7°F (17.6°C) | Light Rain | Mostly Sunny | Slightly High | Average | | July | 69.8°F (21.0°C) | Light Rain | Mostly Sunny | Slightly High | Slightly High | | August | 67.8°F (19.9°C) | Light Rain | Mostly Sunny | Average | Slightly High | | September | 60.8°F (16.0°C) | Light Rain | Mostly Sunny | Slightly High | Average | | October | 49.8°F (9.9°C) | Light Rain | Mostly Sunny | Average | Slightly High | | November | 37.8°F (3.2°C) | Light Rain | Mostly Sunny | Slightly Low | Average | | December | 29.7°F (-1.3°C) | Light Rain | Mostly Cloudy | Slightly Low | Average | ### The nearest major airports for your trip to Sheffield For your trip to Sheffield, Massachusetts, you can fly into several major airports. Hartford, CT ([BDL](https://www.expedia.ca/Bradley-Intl-Airport-Hotels.0-aBDL-0.Travel-Guide-Filter-Hotels)\-Bradley Intl.) is 59.5km away, with nearby hotel options like the [DoubleTree by Hilton Hartford - Bradley Airport](https://www.expedia.ca/Hartford-Hotels-DoubleTree-By-Hilton-Hartford-Bradley-Airport.h14480.Hotel-Information), just 1.6km from the airport. Albany, NY ([ALB](https://www.expedia.ca/Albany-Intl-Airport-Hotels.0-aALB-0.Travel-Guide-Filter-Hotels)\-Albany Intl.) is 80.5km away, offering hotels such as the [Park Manor Hotel](https://www.expedia.ca/Clifton-Park-Hotels-Park-Manor-Hotel.h895584.Hotel-Information), located 12.9km from the airport. Newburgh, NY ([SWF](https://www.expedia.ca/Stewart-Intl-Airport-Hotels.0-aSWF-0.Travel-Guide-Filter-Hotels)\-Stewart Intl.) is 91.7km from Sheffield, with options like [The Dutchess Inn and Spa at Beacon](https://www.expedia.ca/Newburgh-Hotels-The-Dutchess-Inn-And-Spa-At-Beacon.h18730652.Hotel-Information), 9.7km away. Each airport provides convenient access to these hotels, making your stay comfortable as you explore the region. ## Recent reviews of Sheffield hotels ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 5/5 Excellent "We chose this location for our family Christmas getaway because the amenities looked appealing and the price was affordable—and we were more than pleased with our three-night stay. The property is incredibly family-friendly. The pool and arcade had great hours, and while the arcade was small, it offered a fun selection of games. The pool and outdoor hot tub were kept at perfect temperatures, and even when busy, there was plenty of space for everyone. Relaxing in the hot tub during a snowstorm was one of the highlights of our trip. Each night, the common room hosted a movie night, which was wonderful to see families come together and enjoy time as a group. The front desk also offered DVD and game rentals, and it was refreshing to see families playing classic board games and laughing together—a pastime that seems rare these days. The lobby and common areas were spacious and cozy, especially with the warm fireplaces, where our family spent a few hours each evenings playing games. Our suite was roomy, comfortable, and felt like home. The well-stocked kitchen was a bonus. The staff was friendly and accommodating, and having a Stop & Shop directly across the street was incredibly convenient. We are more than pleased with this establishment and would both recommend and return for another family getaway! " A verified traveller stayed at Berkshire Mountain Lodge Posted 3 days ago [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Prospect Berkshires](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/b42c4262_y.jpg) ### Prospect Berkshires 5/5 Excellent "Wonderful stay - the property becomes a beautiful winter wonderland in December! Cabin was warm and well-designed, sauna was amazing and easily accessible all day, the staff was friendly, super responsive and drove us around the property when needed. Would recommend and plan to comeback!" A verified traveller stayed at Prospect Berkshires Posted 3 days ago [](https://expedia.ca/Great-Barrington-Hotels-Prospect-Berkshires.h116739795.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 5/5 Excellent "The room was spotless, staff was friendly, and the facility was extremely clean. If in the area we will definately stay here again." A verified traveller stayed at Holiday Inn Express & Suites Pittsfield - Berkshires by IHG Posted 4 days ago [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 5/5 Excellent "The stay was wonderful! The hotel is VERY clean, comfortable, and the staff are so lovely! I really enjoyed staying here. You're treated like family (in a good way). It is well situated for restaurants and skiing. I will definitely return." A verified traveller stayed at The Yankee, Trademark Collection by Wyndham Posted 4 days ago [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 5/5 Excellent "This is the second time I’ve stayed at The Black Swan for the holidays while visiting my family. I like the fact that breakfast is included and they have everything from the traditional “continental” breakfast fare to hard-boiled eggs and microwave-able breakfast sandwiches. I also like the in-room Keurig coffee maker. The guest WiFi was great - no buffering. " A verified traveller from Rockland stayed at The Black Swan Lee - Lenox, an Ascend Collection Hotel Posted 5 days ago [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 5/5 Excellent "Staff were very friendly and flexible. The rooms were comfortable, spacious and clean. Easy checking and checking out. Plenty of parking. Would definitely stay there again and again. " A verified traveller stayed at Hampton Inn & Suites Berkshires-Lenox Posted 6 days ago [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Courtyard by Marriott Lenox Berkshires](https://images.trvl-media.com/lodging/19000000/18110000/18109200/18109146/b4c52f47_y.jpg) ### Courtyard by Marriott Lenox Berkshires 5/5 Excellent "Clean room, friendly staff" A verified traveller stayed at Courtyard by Marriott Lenox Berkshires Posted 6 days ago [](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 5/5 Excellent "Wonderful stay in a winter wonderland that evening especially with use of the heated pool and hot tub being maintained! Loved it. Shops inside were lovely as well, bars & restaurant on-site were fun with quirky decor. Whole hotel is quirky, which is fun!" A verified traveller stayed at The Red Lion Inn Posted 7 days ago [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551_y.jpg) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires 5/5 Excellent "Very friendly staff. Clean rooms. Great breakfast variety. Would definitely stay again." A verified traveller from Rockville stayed at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires Posted 8 days ago [](https://expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Sheffield? > During the peak season, from June to August, Sheffield experiences a vibrant atmosphere, drawing in visitors eager to enjoy the outdoors. As you wander through the city, you can take advantage of the many opportunities for sightseeing, including the iconic Winter Garden and the fascinating Kelham Island Museum, which highlight the city's rich industrial heritage. > > > For those who appreciate a lively cultural scene, July offers a multitude of events that showcase local music, art, and food. The city's welcoming ambiance is complemented by numerous outdoor dining options, where you can enjoy a meal while soaking in the summer sun. > > > If you are seeking a more budget-friendly experience, consider visiting Sheffield in late autumn, particularly in October. During this time, the crowds diminish, allowing for a more intimate exploration of the city. The autumn foliage adds a beautiful backdrop as you visit attractions like the Millennium Gallery or indulge in the local café culture. ### Can I cancel my hotel reservation on Expedia? ### How can I save on a Sheffield hotel booking with Expedia? ### How much is the nightly rate at a Sheffield hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - More ways to book - [Alford Hotels ](https://www.expedia.ca/Alford-Hotels.d3000421226.Travel-Guide-Hotels) - [Farmstay in Ashley Falls ](https://www.expedia.ca/Ashley-Falls-Agritourism.d901768766462177280-aaAgritourism.Travel-Guide-Accommodation) - [Hotels near Berkshire Botanical Garden ](https://www.expedia.ca/Berkshire-Botanical-Garden-Hotels.0-l553248621532665247-0.Travel-Guide-Filter-Hotels) - [Hotels near Chesterwood ](https://www.expedia.ca/Chesterwood-Hotels.0-l6091841-0.Travel-Guide-Filter-Hotels) - [Inns in Egremont ](https://www.expedia.ca/Egremont-Inns.d553248634998707560-aaInns.Travel-Guide-Accommodation) - 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