Title: Browse the Best Sheffield Resorts | 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 Resort Hotels 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=HOTEL_RESORT&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=HOTEL_RESORT&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=HOTEL_RESORT&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=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Sheffield Resorts ![Property grounds](https://images.trvl-media.com/lodging/108000000/107170000/107165100/107165016/07c04f3e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107170000/107165100/107165016/ffffd558.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107170000/107165100/107165016/1a00deb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool, outdoor pool](https://images.trvl-media.com/lodging/108000000/107170000/107165100/107165016/82887df2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more! Pittsfield 10/10 Exceptional (1) "We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!" [](https://www.expedia.ca/Pittsfield-Hotels-Charming-1-Bedroom-4-Star-Resort-W-Heated-Pool.h107165016.Hotel-Information) ![Room](https://images.trvl-media.com/lodging/14000000/13240000/13232400/13232379/beb021fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/14000000/13240000/13232400/13232379/ab32eed5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room](https://images.trvl-media.com/lodging/14000000/13240000/13232400/13232379/1d5f6f62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/14000000/13240000/13232400/13232379/e8d878d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak 'n Spruce Resort South Lee [](https://www.expedia.ca/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h13232379.Hotel-Information) ![Pool](https://images.trvl-media.com/lodging/107000000/106440000/106433900/106433877/bed449f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/107000000/106440000/106433900/106433877/b484a142.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/107000000/106440000/106433900/106433877/8277dfdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/107000000/106440000/106433900/106433877/8efe8a66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Terrific 2-bedroom resort in Lee with WiFi, fitness room, AC Lee [](https://www.expedia.ca/South-Lee-Hotels-Terrific-2-Bedroom-Resort-In-Lee-With-WiFi.h106433877.Hotel-Information) ![Private kitchen](https://images.trvl-media.com/lodging/101000000/100520000/100513900/100513826/w848h683x89y0-24a11365.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100520000/100513900/100513826/w849h683x87y0-5549676d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/101000000/100520000/100513900/100513826/w848h683x88y0-8da08738.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/101000000/100520000/100513900/100513826/w848h683x88y0-e3a39a10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Mountain Lodge Apt! Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Mountain-Lodge-Apt.h100513826.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/114000000/114000000/113999200/113999147/98b4b879.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/114000000/113999200/113999147/w1024h642x0y21-4ce7f12d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/114000000/113999200/113999147/bb538441.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/114000000/113999200/113999147/81c2cb78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Berkshire Mountain Lodge Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h113999147.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=2025-10-17&endDate=2025-10-18®ionId=157238&adults=2&lodging=HOTEL_RESORT&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-Resort-Hotels.d157238-aaResortHotels.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FSheffield-Resort-Hotels.d157238-aaResortHotels.Travel-Guide-Accommodation) ## Top Sheffield Hotel Reviews ![The Red Lion Inn](//images.trvl-media.com/lodging/6000000/5790000/5780800/5780784/d8bd26bd_y.jpg) ### The Red Lion Inn 10/10 Excellent "Great place! Food excellent ss well!" [](https://expedia.ca/Stockbridge-Hotels-The-Red-Lion-Inn.h5780784.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 "I honestly just spent the night as part of a longer road-trip, but I found it quiet and comfortable, and the room was very clean when I arrived. Slept well, but unfortunately had to leave before breakfast." [](https://expedia.ca/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information) ![The Black Swan Lee - Lenox, an Ascend Collection Hotel](//images.trvl-media.com/lodging/1000000/30000/20500/20447/588051f1_y.jpg) ### The Black Swan Lee - Lenox, an Ascend Collection Hotel 10/10 Excellent "The staff was helpful, friendly. Nice location. The room was very clean and quiet, but so much of the place is brown. Brown carpet, brown paneled walls, brown chair, brown furniture, brown lamps. A minor detraction, but I look at hotel decor with a discerning eye and I like things to be less bland/mundane." [](https://expedia.ca/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information) ![Quality Inn](//images.trvl-media.com/lodging/1000000/130000/128300/128208/62e9a326_y.jpg) ### Quality Inn 10/10 Excellent "Clean Room, good parking, conveniently located near down town." [](https://expedia.ca/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information) ![Berkshires Untold](//images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/c29ce633_y.jpg) ### Berkshires Untold 10/10 Excellent "Absolutely loved this place. It was quant, hip, affordable and just all around stunning! Worth it all! Would stay there again in a heartbeat. " [](https://expedia.ca/Lenox-Hotels-Berkshires-Untold.h76297618.Hotel-Information) ![Berkshire Mountain Lodge](//images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/a007f019_y.jpg) ### Berkshire Mountain Lodge 10/10 Excellent "A bit out dated but nice area for fireplace during winter overlooking the pool. Rugs need to go in the hallways, they are UGLY! Service was friendly, the rooms are equiped with utensils, fridge, microwave etc and spacious. Hot tub and grills. Recommend" [](https://expedia.ca/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.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 "Clean property with plenty to do!" [](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](//images.trvl-media.com/lodging/1000000/120000/119300/119210/6a7ad915_y.jpg) ### Holiday Inn Express & Suites Pittsfield - Berkshires by IHG 10/10 Excellent "Easy to find nice staff very clean facility" [](https://expedia.ca/Pittsfield-Hotels-Holiday-Inn-Express-Pittsfield-Berkshires.h119210.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 "Felt comfortable and safe. Nice pool and gym facility." [](https://expedia.ca/Lenox-Hotels-Hampton-Inn-Suites-Berkshires-Lenox.h1927087.Hotel-Information) ## Find out more about Sheffield ## Sheffield Resorts information | Number of reviews | 1 | | --- | --- | | Accommodation | 5 Resorts | | 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) - [Farmstay in Ashley Falls](https://www.expedia.ca/Ashley-Falls-Agritourism.d901768766462177280-aaAgritourism.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) - 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