Title: Book The Best Hotels in Sheffield, MA for 2026 from CA $105 - 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) ![](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 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=2026-02-16&d1=2026-02-16&endDate=2026-02-18&d2=2026-02-18&amenities=PETS) 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=2026-02-16&d1=2026-02-16&endDate=2026-02-18&d2=2026-02-18&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=2026-02-16&d1=2026-02-16&endDate=2026-02-18&d2=2026-02-18&amenities=SPA_ON_SITE) 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=2026-02-16&d1=2026-02-16&endDate=2026-02-18&d2=2026-02-18&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=2026-02-16&d1=2026-02-16&endDate=2026-02-18&d2=2026-02-18&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=2026-02-16&d1=2026-02-16&endDate=2026-02-18&d2=2026-02-18&travelerType=family_friendly) 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=2026-02-16&d1=2026-02-16&endDate=2026-02-18&d2=2026-02-18&lodging=AGRITOURISM) 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=2026-02-16&d1=2026-02-16&endDate=2026-02-18&d2=2026-02-18&lodging=APARTMENT) 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=2026-02-16&d1=2026-02-16&endDate=2026-02-18&d2=2026-02-18&lodging=COTTAGE) ## Check prices for these dates Tonight [Feb 2 - Feb 3](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-02-02&endDate=2026-02-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Feb 3 - Feb 4](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-02-03&endDate=2026-02-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-02-06&endDate=2026-02-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2026-02-13&endDate=2026-02-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Sheffield hotels ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/143186d3.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) ![Interior detail](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/0603c149.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f060dba9.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 (43 reviews) "Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kristinna [](https://www.expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, seasonal outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/3f4a1adf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/dbcc78d8.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 (1,004 reviews) "Very friendly staff comfy beds!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Giselle CA $126 CA $141 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.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) ![Premium bedding, pillowtop beds, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/dcdd836c.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/9ac40a95.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 (728 reviews) "Great property, very accommodating. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shanice CA $146 CA $163 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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) ![Superior Suite, Private Bathroom (Honeymoon - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/7ac0f2b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Private Bathroom (Clark - Pets Allowed)](https://images.trvl-media.com/lodging/2000000/1510000/1506600/1506594/04b1723e.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) ### Shaker Mill Inn [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) West Stockbridge 9.6/10 Exceptional (444 reviews) "The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carin CA $142 CA $156 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/West-Stockbridge-Hotels-Shaker-Mill-Inn.h1506594.Hotel-Information) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/e459ce18.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/53f3f179.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lake](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/00c971b9.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 (1,001 reviews) "Room was clean and the staff was super friendly and helpful!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ethan CA $133 CA $149 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8.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) ![Standard Room, 2 Queen Beds, Non Smoking | Bathroom](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/591bd0b6.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) ### 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 (1,000 reviews) "This was a perfect place to stay. Reasonably priced, very clean, and the young lady who worked the front desk in the evening was super friendly. We will definitely book here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jerome CA $103 CA $115 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.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) ![Exterior](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/748b4faa.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 (818 reviews) "Unbelieveably clean for the price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Micah [](https://www.expedia.ca/Great-Barrington-Hotels-Monument-Mountain-Motel.h1076188.Hotel-Information) ![In-room safe, desk, laptop workspace, iron/ironing board](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/17f29286.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) ![Gazebo](https://images.trvl-media.com/lodging/1000000/30000/27900/27880/20495b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Howard Johnson by Wyndham Lenox [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) Lenox 7.6/10 Good (830 reviews) "Staff was very friendly and helpful." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pamela CA $94 CA $105 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![In-room safe, desk, free cribs/infant beds, free rollaway beds](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/7c78ca51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom, Non Smoking](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/a393dfb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/e351f473.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1240000/1239700/1239604/c5a54031.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 (567 reviews) "Excellent location!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul Samad CA $102 CA $114 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Great-Barrington-Hotels-Travelodge-By-Wyndham-Great-Barrington-Berkshires.h1239604.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/6a569eff.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) ![Breakfast, dinner served; American cuisine, garden views ](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/4a1ad790.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 (848 reviews) "So charming, clean, thoughtful touches and a really special place!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juliana CA $120 CA $134 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Breakfast, lunch and dinner served](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/27ba18f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/59bbbbcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/bba60f2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/11000000/10250000/10246100/10246064/w696h390x1y0-dec65b39.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 (665 reviews) " Nice staff - beautiful hotel!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARY CA $187 CA $208 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Pittsfield-Hotels-Hilton-Garden-Inn-Lenox-Pittsfield.h10246064.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/251da7fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/3908437c.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) ![Exterior](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/06dae0ff.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 9.8/10 Exceptional (18 reviews) "Spotless rooms and the friendliest service at the front desk! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $189 CA $211 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.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) ![Restaurant](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/226579d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/ed360a9d.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 (828 reviews) "Great overnights stay, wish I was here longer " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $153 CA $198 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/9c157bdc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/b28516d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/04ff4b17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/8000000/7760000/7754000/7753947/30ceb892.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 (414 reviews) "Great breakfast! Had a wonderful stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $143 CA $164 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Torrington-Hotels-Locust-Tree-Bed-And-Breakfast-LLC.h7753947.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) ![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) ![Hallway](https://images.trvl-media.com/lodging/16000000/15790000/15783300/15783244/84c5ab19.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 (291 reviews) "A charming inn in the center of the Berkshires." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Danny CA $196 CA $230 total includes taxes & fees Feb 6 - Feb 7 [](https://www.expedia.ca/Lee-Hotels-Lakehouse-Inn.h15783244.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) ![Standard Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/a831aba7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/460000/459800/459706/47150b36.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/c24971a6.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 (1,000 reviews) "Safe, clean rooms, decent breakfast " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Neil CA $115 CA $128 total includes taxes & fees Feb 22 - Feb 23 [](https://www.expedia.ca/Lee-Hotels-Quality-Inn.h459706.Hotel-Information) ![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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/56630735.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/4000000/3210000/3201500/3201405/390a52f5.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 (1,002 reviews) "Priced very reasonably and the room was clean and comfy!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Wayne CA $80 CA $87 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/West-Stockbridge-Hotels-Pleasant-Valley-Motel-West-Stockbridge.h3201405.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a.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) ![Indoor pool](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/201806cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/77fe0507.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 (826 reviews) "Very comfortable and very close to ski slope and restaurants" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frederick CA $134 CA $180 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/d8fde5b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, blackout drapes, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/320c2d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Studio Sofabed Non Smoking | View from room](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/w3837h2559x0y0-777976aa.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 (1,002 reviews) "The room and amenities were amazing. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kathleen CA $162 CA $181 total includes taxes & fees Feb 8 - Feb 9 [](https://www.expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/f84b737e.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/8000000/7670000/7663800/7663779/6fb451ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 Queen Bed, Mobility Accessible](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/9c5d1ec8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/8000000/7670000/7663800/7663779/8dbc27a7.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 (553 reviews) "Great friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Pablo CA $147 CA $165 total includes taxes & fees Feb 10 - Feb 11 [](https://www.expedia.ca/Great-Barrington-Hotels-The-Briarcliff-Motel.h7663779.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=2026-02-16&endDate=2026-02-17®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) ## Stay near popular Sheffield attractions ### 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://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=553248621532664810) ### Drury Preserve You can take time to visit Drury Preserve during your travels to Sheffield. Make some time to visit the casinos while you're in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909393154894376960) ### Bartholomews Cobble Explore the great outdoors at Bartholomews Cobble, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909390447198502912) ### Lime Kiln Farm Wildlife Sanctuary You can take time to visit Lime Kiln Farm Wildlife Sanctuary during your travels to Sheffield. Make some time to visit the casinos while you're in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909392771425624064) ### Bartholomew's Cobble You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=909390908452102144) ### Thom Reed UFO Monument Park Explore the great outdoors at Thom Reed UFO Monument Park, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area. [See properties](https://www.expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=858298811991220224) ## 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=2026-02-16&endDate=2026-02-17&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) ## Top Sheffield Hotel Reviews ![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "We had a lovely extended family weekend here. The staff was outstanding, every staff member was helpful, friendly and courteous. The large room in back of the lobby was especially helpful for our large group to hang out in and be comfortable. Everyone enjoyed the pool and hot tub despite it being so cold out. The hotel is well maintained. The only small complaint I had was that the bathroom in our room needs to be refreshed. We have already started talking about coming back in the warmer weather to enjoy some of the outdoor activities in in the area." [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG 10/10 Excellent "Great clean room. Staff great. Breakfast and selection great! " [](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) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "Immaculately clean and friendly staff. Easy parking and great breakfast" [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Red Lion Inn](https://images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Great stay. The only thing I would say - and I’ve been staying at the hotel since the 80s - it might be time for a few updates here and there. It runs the risk of going from rustic charm to grandma’s house in the not tooooo distant future. " [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.Hotel-Information) ![Quality Inn](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "This was a perfect place to stay. Reasonably priced, very clean, and the young lady who worked the front desk in the evening was super friendly. We will definitely book here again. " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.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 10/10 Excellent "Clean room, kind and attentive staff" [](https://expedia.ca/Great-Barrington-Hotels-Fairfield-Inn-Suites-By-Marriott-Great-Barrington-LenoxBerkshires.h913175.Hotel-Information) ![Prospect Berkshires](https://images.trvl-media.com/lodging/117000000/116740000/116739800/116739795/b42c4262_y.jpg) ### Prospect Berkshires 10/10 Excellent "Excellent local stay - would recommend to all" [](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 10/10 Excellent "room was very nice " [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![Element Lenox Berkshires](https://images.trvl-media.com/lodging/117000000/116630000/116624600/116624515/c0933de7_y.jpg) ### Element Lenox Berkshires 10/10 Excellent "Awesome " [](https://expedia.ca/Lenox-Hotels-Element-Lenox-Berkshires.h116624515.Hotel-Information) ## More cheap stays in Sheffield ![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 $94 CA $105 total Feb 3 - Feb 4 includes taxes & fees 7.4/10 Good! (829 reviews) [](https://expedia.ca/Lenox-Hotels-Howard-Johnson-By-Wyndham-Lenox.h27880.Hotel-Information) ![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 $115 total Feb 22 - Feb 23 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) ![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 $128 total Feb 22 - Feb 23 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 $126 CA $141 total Feb 9 - Feb 10 includes taxes & fees 9/10 Wonderful! (1,002 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 $146 CA $163 total Feb 4 - Feb 5 includes taxes & fees 8.8/10 Excellent! (728 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=16%2F02%2F2026&endDate=17%2F02%2F2026&selected=1076188&PinnedHotelID=1076188&HadPinnedHotel=true®ionId=157238) 8.8/10 Excellent! (818 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. ## Frequently asked questions ### What is the best area to stay in Sheffield? > Sheffield's town centre is a pleasant and convenient base for exploring the Southern Berkshires. Main Street is where you'll find a selection of antique shops, local eateries, and a few small galleries. The town maintains a relaxed, rural character, making it easy to unwind. > > > Couples looking for a tranquil getaway will appreciate the quiet charm of Sheffield. Many accommodations here offer a peaceful setting, often with views of the surrounding hills, great for relaxing after a day of exploring the region's art and nature. It's also a great base for visiting nearby towns such as Great Barrington. > > > For those interested in outdoor activities and nature, staying in or just outside the town centre provides easy access to local hiking trails and scenic drives. ### What are the best hotels in Sheffield that travellers recommend? > The Wilder House Berkshires, with an outstanding 9.8 rating, is praised by guests for its comfortable and clean rooms. Travellers particularly enjoy the great and delicious complimentary cooked breakfast. The hotel also offers premium bedding, air conditioning, and free self-parking, ensuring a convenient and pleasant stay. ### What are the best family hotels in Sheffield? > This highly-rated accommodation, with an impressive 9.8 review score, offers a welcoming stay for families. Guests consistently praise the comfortable and clean rooms, ensuring a pleasant environment for everyone. A significant advantage for families is the complimentary breakfast, including cooked options, which guests describe as great and delicious. Free toiletries, free WiFi, and free self-parking add to the convenience and value. The availability of a free crib further highlights its family-friendly focus, making it easier for parents travelling with infants. ### What hotels in Sheffield offer free breakfast? > This highly-rated property, with an impressive 9.8 review score, offers both free breakfast and free cooked breakfast, which guests consistently describe as great and delicious. The rooms are noted for being comfortable and clean, and the hotel also provides free WiFi, free self-parking, and premium bedding. Additionally, it is conveniently located just 10.2 km from the Housatonic River. ### What are the best budget hotels in Sheffield? > The Wilder House Berkshires has an exceptional review rating of 9.8\. Guests consistently mention the comfortable and clean rooms, along with the great and delicious breakfast. This hotel provides a range of complimentary amenities, including free cooked breakfast, free toiletries, free WiFi, and free self-parking. The rooms also feature premium bedding and air conditioning for added comfort. It is located approximately 10.2 km from the Housatonic River. View all [budget hotels in Sheffield](https://www.expedia.ca/Sheffield-Hotels-Cheap-Hotels.0-0-d157238-tCheapHotels.Travel-Guide-Filter-Hotels) ### When is the best time to go to Sheffield? > For those who enjoy warm weather and outdoor adventures, the summer months from June to August are ideal. The Berkshires are lush and green during this period, superb for hiking, cycling, and enjoying the numerous lakes and rivers. You'll find many local farms offering fresh produce, and outdoor events are plentiful. > > > If you're particularly interested in the stunning autumn foliage, late September through October is the most picturesque time to visit. The hillsides transform into a spectacular display of reds, oranges, and yellows, making it superb for scenic drives and photography. This period is very popular, so booking accommodation well in advance is recommended. > > > For winter sports enthusiasts, December through March offers opportunities for skiing, snowboarding, and snowshoeing at nearby resorts. The landscape is often covered in snow, creating a serene and beautiful setting, though some smaller shops and attractions might have reduced hours. > > > Spring, from April to May, sees the awakening of the landscape with blooming flowers and budding trees. ### 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 Rental - 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) - [B&B in Great Barrington ](https://www.expedia.ca/Great-Barrington-Bed-And-Breakfast.d110336-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Castles in Great Barrington ](https://www.expedia.ca/Great-Barrington-Castles.d110336-aaCastles.Travel-Guide-Accommodation) - [Guest Houses in Great Barrington ](https://www.expedia.ca/Great-Barrington-Guest-Houses.d110336-aaGuestHouses.Travel-Guide-Accommodation) - [Boutique Hotels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Boutique-Hotel.0-0-d110336-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Cheap-Hotels.0-0-d110336-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Hotel-With-Pool.0-0-d110336-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Hotels with Hot Tubs in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Hotels-With-Hot-Tubs.0-0-d110336-tHotelsWithHotTubs.Travel-Guide-Filter-Hotels) - [Hotels with an Indoor Pool in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Hotels-With-Indoor-Pool.0-0-d110336-tHotelswithIndoorPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Luxury-Hotel.0-0-d110336-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Pet-Friendly Hotels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Pet-Friendly-Hotel.0-0-d110336-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [Spa Hotels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Hotels-Spa-Hotel.0-0-d110336-tSpaHotel.Travel-Guide-Filter-Hotels) - [Great Barrington Hotels ](https://www.expedia.ca/Great-Barrington-Hotels.d110336.Travel-Guide-Hotels) - [Inns in Great Barrington ](https://www.expedia.ca/Great-Barrington-Inns.d110336-aaInns.Travel-Guide-Accommodation) - [Motels in Great Barrington ](https://www.expedia.ca/Great-Barrington-Motels.d110336-aaMotels.Travel-Guide-Accommodation) - [Resorts in Great Barrington ](https://www.expedia.ca/Great-Barrington-Resort-Hotels.d110336-aaResortHotels.Travel-Guide-Accommodation) - [Housatonic Hotels ](https://www.expedia.ca/Housatonic-Hotels.d3000441135.Travel-Guide-Hotels) - [Hotels near Jacob's Pillow ](https://www.expedia.ca/Jacobs-Pillow-Hotels.0-l553248621532666599-0.Travel-Guide-Filter-Hotels) - [Lee Hotels ](https://www.expedia.ca/Lee-Hotels.d8572.Travel-Guide-Hotels) - [Hotels near Lee Premium Outlets ](https://www.expedia.ca/Lee-Premium-Outlets-Hotels.0-l6127084-0.Travel-Guide-Filter-Hotels) - [Hotels near Mahaiwe Performing Arts Center ](https://www.expedia.ca/Mahaiwe-Performing-Arts-Center-Hotels.0-l553248621532665242-0.Travel-Guide-Filter-Hotels) - [Farmstay in Mill River ](https://www.expedia.ca/Mill-River-Agritourism.d3000748895-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Mill River ](https://www.expedia.ca/Mill-River-Apart-Hotels.d3000748895-aaApartHotels.Travel-Guide-Accommodation) - [Cabin Rentals in Mill River ](https://www.expedia.ca/Mill-River-Cabins.d3000748895-aaCabins.Travel-Guide-Accommodation) - [Chalets in Mill River ](https://www.expedia.ca/Mill-River-Chalets.d3000748895-aaChalets.Travel-Guide-Accommodation) - [Cottages in Mill River ](https://www.expedia.ca/Mill-River-Cottages.d3000748895-aaCottages.Travel-Guide-Accommodation) - [Guest Houses in Mill River ](https://www.expedia.ca/Mill-River-Guest-Houses.d3000748895-aaGuestHouses.Travel-Guide-Accommodation) - [Mill River Hotels ](https://www.expedia.ca/Mill-River-Hotels.d3000748895.Travel-Guide-Hotels) - [Inns in Mill River ](https://www.expedia.ca/Mill-River-Inns.d3000748895-aaInns.Travel-Guide-Accommodation) - [Motels in Mill River ](https://www.expedia.ca/Mill-River-Motels.d3000748895-aaMotels.Travel-Guide-Accommodation) - [Resorts in Mill River ](https://www.expedia.ca/Mill-River-Resort-Hotels.d3000748895-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Mill River ](https://www.expedia.ca/Mill-River-Townhomes.d3000748895-aaTownhomes.Travel-Guide-Accommodation) - [Monterey Hotels ](https://www.expedia.ca/Monterey-Hotels.d6005411.Travel-Guide-Hotels) - [Farmstay in Mount Washington ](https://www.expedia.ca/Mount-Washington-Agritourism.d553248634999242901-aaAgritourism.Travel-Guide-Accommodation) - [Aparthotels in Mount Washington ](https://www.expedia.ca/Mount-Washington-Apart-Hotels.d553248634999242901-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Mount Washington ](https://www.expedia.ca/Mount-Washington-Apartments.d553248634999242901-aaApartments.Travel-Guide-Accommodation) - [B&B in Mount Washington ](https://www.expedia.ca/Mount-Washington-Bed-And-Breakfast.d553248634999242901-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Chalets in Mount Washington ](https://www.expedia.ca/Mount-Washington-Chalets.d553248634999242901-aaChalets.Travel-Guide-Accommodation) - [Condo Resorts in Mount Washington ](https://www.expedia.ca/Mount-Washington-Condominium-Resort.d553248634999242901-aaCondominiumResort.Travel-Guide-Accommodation) - [Guest Houses in Mount Washington ](https://www.expedia.ca/Mount-Washington-Guest-Houses.d553248634999242901-aaGuestHouses.Travel-Guide-Accommodation) - [Holiday Park Resorts in Mount Washington ](https://www.expedia.ca/Mount-Washington-Holiday-Parks.d553248634999242901-aaHolidayParks.Travel-Guide-Accommodation) - [Cheap Hotels in Mount Washington ](https://www.expedia.ca/Mount-Washington-Hotels-Cheap-Hotels.0-0-d553248634999242901-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels with a Pool in Mount Washington ](https://www.expedia.ca/Mount-Washington-Hotels-Hotel-With-Pool.0-0-d553248634999242901-tHotelwithPool.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Mount Washington ](https://www.expedia.ca/Mount-Washington-Hotels-Luxury-Hotel.0-0-d553248634999242901-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Mount Washington Hotels ](https://www.expedia.ca/Mount-Washington-Hotels.d553248634999242901.Travel-Guide-Hotels) - [Inns in Mount Washington ](https://www.expedia.ca/Mount-Washington-Inns.d553248634999242901-aaInns.Travel-Guide-Accommodation) - [Lodges in Mount Washington ](https://www.expedia.ca/Mount-Washington-Lodges.d553248634999242901-aaLodges.Travel-Guide-Accommodation) - [Motels in Mount Washington ](https://www.expedia.ca/Mount-Washington-Motels.d553248634999242901-aaMotels.Travel-Guide-Accommodation) - [Resorts in Mount Washington ](https://www.expedia.ca/Mount-Washington-Resort-Hotels.d553248634999242901-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in Mount Washington ](https://www.expedia.ca/Mount-Washington-Townhomes.d553248634999242901-aaTownhomes.Travel-Guide-Accommodation) - [Hotels near National Shrine of the Divine Mercy ](https://www.expedia.ca/National-Shrine-Of-The-Divine-Mercy-Hotels.0-l553248621532665250-0.Travel-Guide-Filter-Hotels) - [B&B in New Marlborough ](https://www.expedia.ca/New-Marlborough-Bed-And-Breakfast.d137834-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in New Marlborough ](https://www.expedia.ca/New-Marlborough-Guest-Houses.d137834-aaGuestHouses.Travel-Guide-Accommodation) - [Boutique Hotels in New Marlborough ](https://www.expedia.ca/New-Marlborough-Hotels-Boutique-Hotel.0-0-d137834-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Luxury Hotels in New Marlborough ](https://www.expedia.ca/New-Marlborough-Hotels-Luxury-Hotel.0-0-d137834-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [New Marlborough Hotels ](https://www.expedia.ca/New-Marlborough-Hotels.d137834.Travel-Guide-Hotels) - [Resorts in New Marlborough ](https://www.expedia.ca/New-Marlborough-Resort-Hotels.d137834-aaResortHotels.Travel-Guide-Accommodation) - [Townhomes in New Marlborough ](https://www.expedia.ca/New-Marlborough-Townhomes.d137834-aaTownhomes.Travel-Guide-Accommodation) - [Hotels near Norman Rockwell Museum ](https://www.expedia.ca/Norman-Rockwell-Museum-Hotels.0-l6091839-0.Travel-Guide-Filter-Hotels) - [Townhomes in North Egremont ](https://www.expedia.ca/North-Egremont-Townhomes.d553248635976384751-aaTownhomes.Travel-Guide-Accommodation) - [Otis Hotels ](https://www.expedia.ca/Otis-Hotels.d6005412.Travel-Guide-Hotels) - [Hotels near Otis Reservoir ](https://www.expedia.ca/Otis-Reservoir-Hotels.0-l553248621532666595-0.Travel-Guide-Filter-Hotels) - [Hotels near Otis Ridge ](https://www.expedia.ca/Otis-Ridge-Hotels.0-l553248621532666596-0.Travel-Guide-Filter-Hotels) - [Sandisfield Hotels ](https://www.expedia.ca/Sandisfield-Hotels.d6005416.Travel-Guide-Hotels) - [Hotels near Ski Butternut ](https://www.expedia.ca/Ski-Butternut-Hotels.0-l6182072-0.Travel-Guide-Filter-Hotels) - [B&B in South Egremont ](https://www.expedia.ca/South-Egremont-Bed-And-Breakfast.d183341-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Pet-Friendly Hotels in South Egremont ](https://www.expedia.ca/South-Egremont-Hotels-Pet-Friendly-Hotel.0-0-d183341-tPetfriendlyHotel.Travel-Guide-Filter-Hotels) - [South Egremont Hotels ](https://www.expedia.ca/South-Egremont-Hotels.d183341.Travel-Guide-Hotels) - [Inns in South Egremont ](https://www.expedia.ca/South-Egremont-Inns.d183341-aaInns.Travel-Guide-Accommodation) - [South Lee Hotels ](https://www.expedia.ca/South-Lee-Hotels.d183343.Travel-Guide-Hotels) - [Luxury Hotels in Southfield ](https://www.expedia.ca/Southfield-Hotels-Luxury-Hotel.0-0-d6339785-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Southfield Hotels ](https://www.expedia.ca/Southfield-Hotels.d6339785.Travel-Guide-Hotels) - [Townhomes in Southfield ](https://www.expedia.ca/Southfield-Townhomes.d6339785-aaTownhomes.Travel-Guide-Accommodation) - [Stockbridge Hotels ](https://www.expedia.ca/Stockbridge-Hotels.d162575.Travel-Guide-Hotels) - [Hotels near Tanglewood Music Center ](https://www.expedia.ca/Tanglewood-Music-Center-Hotels.0-l503292-0.Travel-Guide-Filter-Hotels) - [The Berkshires Hotels ](https://www.expedia.ca/The-Berkshires-Hotels.d6047665.Travel-Guide-Hotels) - [Hotels near The Mount ](https://www.expedia.ca/The-Mount-Hotels.0-l553248621532665265-0.Travel-Guide-Filter-Hotels) - [Hotels near Tyringham Cobble ](https://www.expedia.ca/Tyringham-Cobble-Hotels.0-l553248621532665261-0.Travel-Guide-Filter-Hotels) - [Tyringham Hotels ](https://www.expedia.ca/Tyringham-Hotels.d183347.Travel-Guide-Hotels) - [West Stockbridge Hotels ](https://www.expedia.ca/West-Stockbridge-Hotels.d173346.Travel-Guide-Hotels) - [Flights to Great Barrington ](https://www.expedia.ca/Cheap-Flights-To-Great-Barrington.d110336.Travel-Guide-Flights) - [Flights from Monterey ](https://www.expedia.ca/lp/flights/6005411/flights-from-monterey) - [Visit Ashley Falls ](https://www.expedia.ca/Ashley-Falls.dx901768766462177280) - [Great Barrington Vacations ](https://www.expedia.ca/Great-Barrington.d110336.Destination-Travel-Guides) - [Visit Great Barrington ](https://www.expedia.ca/Great-Barrington.dx110336) - [Lake Buel ](https://www.expedia.ca/Lake-Buel-Great-Barrington.d553248635976196476.Vacation-Attraction) - [Lake Mansfield Park ](https://www.expedia.ca/Lake-Mansfield-Park-Great-Barrington.d553248621560926695.Vacation-Attraction) - [Visit North Egremont ](https://www.expedia.ca/North-Egremont.dx553248635976384751) - [South Egremont Vacations ](https://www.expedia.ca/South-Egremont.d183341.Destination-Travel-Guides) - [Visit South Egremont ](https://www.expedia.ca/South-Egremont.dx183341) - [Car rental Great Barrington ](https://www.expedia.ca/Car-Rentals-In-Great-Barrington.d110336.Car-Rental-Guide) - [Enterprise Rental Cars in Great Barrington ](https://www.expedia.ca/Enterprise-Car-Rentals-In-Great-Barrington.d110336-c15.Car-Rental-Guide-Suppliers) - [Enterprise Rental Cars in New Marlborough ](https://www.expedia.ca/Enterprise-Car-Rentals-In-New-Marlborough.d137834-c15.Car-Rental-Guide-Suppliers) - [Mex Rent A Car Rental Cars in Mount Washington ](https://www.expedia.ca/Mex-Rent-A-Car-Car-Rentals-In-Mount-Washington.d553248634999242901-c1084.Car-Rental-Guide-Suppliers) - [Great Barrington Vacation Rentals ](https://www.expedia.ca/Great-Barrington-Vacation-Rentals.d110336.Travel-Guide-VacationRentals) - [Mount Washington Vacation Rentals ](https://www.expedia.ca/Mount-Washington-Vacation-Rentals.d553248634999242901.Travel-Guide-VacationRentals) - [Book Hotels in Sheffield on Expedia.com ](https://www.expedia.com/Sheffield-Hotels.d157238.Travel-Guide-Hotels) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app