Title: Sheffield Chalets | Expedia.ca [Hotels in Sheffield](https://expedia.ca/Sheffield-Hotels.d157238.Travel-Guide-Hotels)[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) ![](https://mediaim.expedia.com/destination/1/0c91d6ccb27784bad8a181efd70e605a.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Chalets in Sheffield ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=157238&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=CHALET&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Sheffield Chalets ![Outdoor dining](https://images.trvl-media.com/lodging/83000000/82470000/82464100/82464081/2748140e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/83000000/82470000/82464100/82464081/2cc76c7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/83000000/82470000/82464100/82464081/8d48e384.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/83000000/82470000/82464100/82464081/27cee0e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Little Longbow Lakefront Chalet Becket 9.6/10 Exceptional (16) "Very pleasant place! Recommend!!! " [](https://www.expedia.ca/Becket-Hotels-Little-Longbow-Lakefront-Chalet.h82464081.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32410000/32404800/32404738/0c48dd95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/33000000/32410000/32404800/32404738/a5f944f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/33000000/32410000/32404800/32404738/648486e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, music library, stereo](https://images.trvl-media.com/lodging/33000000/32410000/32404800/32404738/466c6ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach Monterey 9.8/10 Exceptional (25) "Tastefully decorated, great view, and lots of peace and quiet. All the amenities worked, and the house was equipped with everything you need. A great place for families or a larger group of close friends. Would definitely recommend " [](https://www.expedia.ca/Monterey-Hotels-Private-Berkshires-Hilltop-Retreat-W-Magic-View.h32404738.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/105000000/104200000/104196300/104196277/w1024h583x0y51-2dd19611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/105000000/104200000/104196300/104196277/36628664.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104200000/104196300/104196277/w904h683x60y0-f2601166.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, books, stereo](https://images.trvl-media.com/lodging/105000000/104200000/104196300/104196277/w507h683x259y0-f49b9cfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SRC-Hudson Valley/Berkshires Cultural Corridor Canaan 10/10 Exceptional (1) "Property was beautiful, as described. Our group consisted of us, our 2 sons and 2 daughters in law. The property met all of our needs, was quite perfect actually. The location midway between the Berkshires and Hudson was ideal. Communication with owners was great, no concerns. " [](https://www.expedia.ca/Canaan-Hotels-SRC-Hudson-ValleyBerkshires-Cultural-Corridor.h104196277.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=2025-10-13&endDate=2025-10-14®ionId=157238&adults=2&lodging=CHALET&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-Chalets.d157238-aaChalets.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Chalets.d157238-aaChalets.Travel-Guide-Accommodation) ## Top Sheffield Hotel Reviews ![The Ponds at Foxhollow](//images.trvl-media.com/lodging/19000000/18110000/18110000/18109961/ebd04e74_y.jpg) ### The Ponds at Foxhollow 10/10 Excellent "Was a nice place to stay" [](https://expedia.ca/Lenox-Hotels-The-Ponds-At-Foxhollow-By-Capital-Vacations.h18109961.Hotel-Information) ![Wilder House Berkshires](//images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f0c223e5_y.jpg) ### Wilder House Berkshires 10/10 Excellent "Highly recommend this beautiful bed & breakfast! The room was wonderful and overlooked the property, the breakfast was delicious, and the hospitality was amazing. I had a fantastic stay, and will definitely stay at The Wilder House again when I'm in the area." [](https://expedia.ca/Sheffield-Hotels-Wilder-House-Berkshires.h105813835.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "Clean and spacious one bedroom suite with well stocked kitchen. Large indoor pool and outdoor year round Jacuzzi are wonderful. Also very affordable. Second time staying here and will stay here again. " [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "What a beautiful place. I wish I could have stayed longer. Top notch!" [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Holiday Inn Express & Suites Pittsfield - Berkshires by IHG](//images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "Very nice hotel" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.Hotel-Information) ![The Yankee, Trademark Collection by Wyndham](//images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg) ### The Yankee, Trademark Collection by Wyndham 10/10 Excellent "It's just a nice place and the staff is very nice " [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![Hampton Inn & Suites Berkshires-Lenox](//images.trvl-media.com/lodging/2000000/1930000/1927100/1927087/59f14822_y.jpg) ### Hampton Inn & Suites Berkshires-Lenox 10/10 Excellent "Excellent hotel. Great staff. " [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](//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 10/10 Excellent "The room was fantastic - lots of space and well laid out. Having a kitchen is always very helpful. The property was well kept and clean. I love the rustic vibe. The amenities were awesome - the kids spent all day in the large outdoor pool. We also enjoyed the arcade and mini-golf. The whole area is clean and comfortable. Staff were very responsive through text - which was handy. We had a little issue, but it was handled quickly. All-in-all, the whole family loved the room, had a great time at the resort, and felt welcomed by the staff. We look forward to coming back again next year. " [](https://expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Very good " [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ## Find out more about Sheffield ## Sheffield Chalets information | Number of reviews | 41 | | --- | --- | | Accommodation | 3 Chalets | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [3 Star Hotels in The Berkshires](https://www.expedia.ca/3Star-The-Berkshires-Hotels.s30-0-d6047665.Travel-Guide-Filter-Hotels) - [5 Star Hotels in The Berkshires](https://www.expedia.ca/5Star-The-Berkshires-Hotels.s50-0-d6047665.Travel-Guide-Filter-Hotels) - [Alford Hotels](https://www.expedia.ca/Alford-Hotels.d3000421226.Travel-Guide-Hotels) - 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