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 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=2026-01-13&d1=2026-01-13&endDate=2026-01-15&d2=2026-01-15&amenities=SPA_ON_SITE) 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=2026-01-13&d1=2026-01-13&endDate=2026-01-15&d2=2026-01-15&amenities=POOL) 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=2026-01-13&d1=2026-01-13&endDate=2026-01-15&d2=2026-01-15&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=2026-01-13&d1=2026-01-13&endDate=2026-01-15&d2=2026-01-15&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=2026-01-13&d1=2026-01-13&endDate=2026-01-15&d2=2026-01-15&lodging=CABIN) Farm [](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=2026-01-13&d1=2026-01-13&endDate=2026-01-15&d2=2026-01-15&lodging=AGRITOURISM) 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=2026-01-13&d1=2026-01-13&endDate=2026-01-15&d2=2026-01-15&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=2026-01-13&d1=2026-01-13&endDate=2026-01-15&d2=2026-01-15&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=2026-01-13&d1=2026-01-13&endDate=2026-01-15&d2=2026-01-15&lodging=APARTMENT) ## Check prices for these dates Tonight [Dec 30 - Dec 31](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-12-30&endDate=2025-12-31&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 31 - Jan 1](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-12-31&endDate=2026-01-01&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) ![Garden](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f8f74b93.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) ### Wilder House Berkshires [](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) Sheffield 9.8/10 Exceptional (41) "Room was very cozy and beautiful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kiersten CA $243 CA $272 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/be126a14.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/e2e7e72f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/62ab3ea3.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) "Room was very clean and nice!!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $139 CA $156 total includes taxes & fees Jan 28 - Jan 29, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker, dining tables](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/5fd0e723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/b38994ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/754813dc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Element Lenox Berkshires [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) Lenox 9.6/10 Exceptional (14) "Rooms were very clean and spacious." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Morgan Traveling for leisure CA $185 CA $206 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/05418243.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 - Lenox South [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) Lee 8.4/10 Very good (1002) "The room was very clean and tidy!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Emily Traveling for leisure CA $115 CA $129 total includes taxes & fees Jan 18 - Jan 19, 2026 [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.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) ![Superior Room, 1 King Bed, Jetted Tub | Jetted tub](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/f3c92221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Yankee, Trademark Collection by Wyndham [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) Lenox 9.2/10 Wonderful (1003) "the room was extremely clean and beautiful" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Debra Traveling for leisure CA $138 CA $154 total includes taxes & fees Jan 7 - Jan 8, 2026 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7f86e411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Bedrooms, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/723a5f12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/fd39ba7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Travelodge by Wyndham Great Barrington Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) Great Barrington 7.6/10 Good (565) "the rooms are always clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah Traveling with family CA $103 CA $115 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ca1036e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/ba9d3ff8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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 (1002) "The coffee machine was available 24/7 and it made a pretty good mocha!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) terri Traveling for leisure and business CA $142 CA $159 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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) ![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) ### Hampton Inn & Suites Berkshires-Lenox [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) Lenox 9.2/10 Wonderful (1004) "Was looking forward to relaxing in the pool" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mark Traveling with partner CA $152 CA $170 total includes taxes & fees Jan 25 - Jan 26, 2026 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.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) ![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) ![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) ![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) ### Shaker Mill Inn [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) West Stockbridge 9.6/10 Exceptional (439) "Very cute and clean room." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen Traveling for leisure CA $148 CA $163 total includes taxes & fees Jan 6 - Jan 7, 2026 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.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/2000000/1080000/1076200/1076188/748b4faa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/a1ad800b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/83dd2b57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Monument Mountain Motel [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) Great Barrington 9.0/10 Wonderful (811) "It is also walking distance to several good restaurants." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rolland Traveling solo [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/1d50a551.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/f2aaf746.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/15c993a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/32c535e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) Great Barrington 9.4/10 Exceptional (759) "the room spacious and clean, and plenty of breakfast items to choose from" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Denise CA $185 CA $206 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/5fa17ca2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/b6081d93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Snack bar](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/1715f4d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/507a7437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Lenox Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) Pittsfield 9.2/10 Wonderful (659) "Lovely hotel, room was great along with the staff and the grounds where beautiful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vicki Traveling with family CA $175 CA $195 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/35c64b84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/69e559b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/7062b6be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio Suite, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/5a6f7f91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) Lenox 7.6/10 Good (828) "The room was surprisingly spacious and well appointed." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Henry CA $108 CA $121 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 King Bed, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/18ef112b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1650f935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/1d183ca9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Great Barrington [](https://www.expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) Great Barrington 8.4/10 Very good (1001) "The room were clean and comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Victoria Traveling for leisure CA $103 CA $116 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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) ![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) ![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) ### The Red Lion Inn [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) Stockbridge 8.8/10 Excellent (1002) "The room was very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joyce Traveling for leisure CA $187 CA $271 total includes taxes & fees Jan 14 - Jan 15, 2026 [](https://www.expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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) ![1 bedroom, in-room safe, desk, iron/ironing board](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/b1e93ecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/7ffdc0f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/6761ce21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) Pittsfield 9.0/10 Wonderful (798) "Great kitchen area and living room and good size bedroom and bathroom." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Traveling for leisure CA $135 CA $181 total includes taxes & fees Jan 20 - Jan 21, 2026 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/aaa7fba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/c97f0de6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/ebf28595.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) "the Berkshires provide plenty of opportunities for beauty, well designed gardens, places to walk and relax" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marcy Traveling for leisure CA $150 CA $168 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/9b821fe1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/2558ee66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/cdf64ef8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pleasant Valley Motel West Stockbridge [](https://www.expedia.ca/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) West Stockbridge 6.8/10 (1003) "Priced very reasonably and the room was clean and comfy!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne Traveling for leisure CA $71 CA $78 total includes taxes & fees Jan 16 - Jan 17, 2026 [](https://www.expedia.ca/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/fb8a0016.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/9fc87fbd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/fd1046f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/9c157bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Locust Tree Bed and Breakfast LLC [](https://www.expedia.ca/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.Hotel-Information) East Canaan 9.0/10 Wonderful (413) "Bed was very comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael Traveling solo CA $144 CA $165 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/119300/119210/2b026b4b.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/a89bc327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) Pittsfield 9.2/10 Wonderful (71) "Hotel in new condition and very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn Traveling with partner CA $168 CA $187 total includes taxes & fees Jan 4 - Jan 5, 2026 [](https://www.expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-13&endDate=2026-01-14®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=2026-01-13&endDate=2026-01-14&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 $103 CA $116 total Jan 14 - Jan 15, 2026 includes taxes & fees 8.4/10 Very Good! (1,000 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 4 - Jan 5, 2026 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 $115 CA $129 total Jan 18 - Jan 19, 2026 includes taxes & fees 8.2/10 Very Good! (1,002 reviews) [](https://expedia.ca/Lee-Hotels-Quality-Inn.h459706.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 $138 CA $154 total Jan 7 - Jan 8, 2026 includes taxes & fees 9/10 Wonderful! (1,000 reviews) [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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 $139 CA $156 total Jan 28 - Jan 29, 2026 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) ![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=13%2F01%2F2026&endDate=14%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 ![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 2 days ago [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.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 3 days ago [](https://expedia.ca/Lenox-Hotels-Courtyard-By-Marriott-Lenox-Berkshires.h18109146.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 5 days ago [](https://expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![Berkshires Untold](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 5/5 Excellent "The hotel is very nice and the employees are wonderful. Thank you!" A verified traveller stayed at Berkshires Untold Posted 5 days ago [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.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 bed was very comfortable. The staff was helpful and courteous" A verified traveller stayed at The Yankee, Trademark Collection by Wyndham Posted 6 days ago [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/e153ce9c_y.jpg) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG 5/5 Excellent "Perfect for a weekend away. Stagg was friendly. Room was clean and spacious. It was everything we needed and more." A verified traveller stayed at Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG Posted 6 days ago [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.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 "Extremely impressed by this hotel. The staff was very friendly and professional. The rooms were so comfortable and high quality everything! Check in and check out was easy. Highly recommend!" A verified traveller stayed at Holiday Inn Express & Suites Pittsfield - Berkshires by IHG Posted 8 days ago [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Wilder House Berkshires](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f0c223e5_y.jpg) ### Wilder House Berkshires 5/5 Excellent "The place is lovely, room is cozy, and the bed is comfy" A verified traveller stayed at Wilder House Berkshires Posted 8 days ago [](https://expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 5/5 Excellent "Very professional service. Great staff." A verified traveller stayed at Berkshire Mountain Lodge Posted 8 days ago [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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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