Title: Visit Sheffield: Best of Sheffield Tourism | Expedia Travel Guide - 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) # Sheffield ## Travel Guide ![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=1040&h=580&q=mediumHigh) ![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=1040&h=580&q=mediumHigh) ![Sheffield Covered Bridge, rebuilt after 1994 fire.](https://images.trvl-media.com/place/157238/7a5e67d5-5a9a-41d6-9c25-f46a4b9b7289.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Sheffield Things to do - Sheffield Hotel Deals - Vacation Rentals in Sheffield ![Wilder House Berkshires](https://images.trvl-media.com/lodging/106000000/105820000/105813900/105813835/f0c223e5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wilder House Berkshires 48 S Main Street Sheffield MA CA $249 CA $279 total Feb 26 - Feb 27 includes taxes & fees Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ... 9.8/10 Exceptional! (43 reviews) Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. Reviewed on Jan 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=26%2F02%2F2026&endDate=27%2F02%2F2026&selected=105813835&PinnedHotelID=105813835&HadPinnedHotel=true®ionId=157238) ![Guesthouse Cabin vacation rentals in Berkshire County](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Guesthouse Cabin vacation rentals in Berkshire County Sheffield MA CA $537 CA $949 total Feb 9 - Feb 10 includes taxes & fees Stay at this cabin in Sheffield. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Mount Everett State Reservation and Plaintain Pond ... 10/10 Exceptional! (9 reviews) We were a group of moms who snuck away for the night and this cabin was the perfect retreat. Well stocked and very cozy on a winter night. We had to leave very early the next morning to beat a snowstorm and the very long driveway was already sanded and we felt very safe. Lisette was great to work ... Reviewed on Jan 29, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&selected=99962392&PinnedHotelID=99962392&HadPinnedHotel=true®ionId=157238) ![Antique Farmhouse Totally Restored ](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/46c8a41a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Antique Farmhouse Totally Restored Sheffield MA Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Mount Riga State Park ... 9.6/10 Exceptional! (62 reviews) We had a great stay. There is lots of room to spread out for a larger group. The furnishings and decorations are wonderful and eccentric, and the property has a rich history, very tastefully preserved. The kids loved the room with gymnastic rings and feeding the highland cattle across the road. Overall, ... Reviewed on Dec 27, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=27129515&PinnedHotelID=27129515&HadPinnedHotel=true®ionId=157238) [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=27129515&PinnedHotelID=27129515&HadPinnedHotel=true®ionId=157238) [See all 1,272 properties in Sheffield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026®ionId=157238) 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. ![Guesthouse Cabin vacation rentals in Berkshire County](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/9fa6f837_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Guesthouse Cabin vacation rentals in Berkshire County Sheffield MA Stay at this cabin in Sheffield. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Mount Everett State Reservation and Plaintain Pond ... 10/10 Exceptional! (9 reviews) We were a group of moms who snuck away for the night and this cabin was the perfect retreat. Well stocked and very cozy on a winter night. We had to leave very early the next morning to beat a snowstorm and the very long driveway was already sanded and we felt very safe. Lisette was great to work ... Reviewed on Jan 29, 2026 [](https://expedia.ca/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information) ![Antique Farmhouse Totally Restored ](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/46c8a41a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Antique Farmhouse Totally Restored Sheffield MA Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Mount Riga State Park ... 9.6/10 Exceptional! (62 reviews) We had a great stay. There is lots of room to spread out for a larger group. The furnishings and decorations are wonderful and eccentric, and the property has a rich history, very tastefully preserved. The kids loved the room with gymnastic rings and feeding the highland cattle across the road. Overall, ... Reviewed on Dec 27, 2025 [](https://expedia.ca/Sheffield-Hotels-Antique-Farmhouse-Totally-Restored.h27129515.Hotel-Information) ![The Race Mountain House](https://images.trvl-media.com/lodging/109000000/108970000/108962900/108962866/b98061a9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Race Mountain House Sheffield MA Stay at this vacation home in Sheffield. Enjoy laundry facilities, patios, and in-room fireplaces. Popular attractions Mount Everett State Reservation and Drury ... 9.4/10 Exceptional! (6 reviews) We had a wonderful 2-day stay at this charming house! The location is perfect, nestled near the mountains with breathtaking views. The house itself is clean and cozy, with comfortable bedrooms stocked with extra blankets and pillows. The spacious bathrooms (both upstairs and downstairs!) had plenty ... Reviewed on Jan 3, 2026 [](https://expedia.ca/Sheffield-Hotels-The-Race-Mountain-House.h108962866.Hotel-Information) [See all properties in Sheffield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=157238&sort=VACATION_RENTAL) 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. ## Check Sheffield hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157238&startDate=2026-02-08&endDate=2026-02-09)[Feb 8 - Feb 9](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157238&startDate=2026-02-08&endDate=2026-02-09) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157238&startDate=2026-02-09&endDate=2026-02-10)[Feb 9 - Feb 10](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157238&startDate=2026-02-09&endDate=2026-02-10) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157238&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026)[Feb 13 - Feb 15](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=157238&startDate=13%2F02%2F2026&endDate=15%2F02%2F2026) ### Popular places to visit #### 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. [](https://expedia.ca/Magnolia-Bluffs-Casino-Sheffield.d553248621532644877.Vacation-Attraction) #### 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. [](https://expedia.ca/Ashley-House-Sheffield.d553248621532664810.Vacation-Attraction) #### 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. [](https://expedia.ca/Drury-Preserve-Sheffield.d909393154894376960.Vacation-Attraction) #### 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. [](https://expedia.ca/Bartholomews-Cobble-Sheffield.d909390447198502912.Vacation-Attraction) #### 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. [](https://expedia.ca/Lime-Kiln-Farm-Wildlife-Sanctuary-Sheffield.d909392771425624064.Vacation-Attraction) #### 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. [](https://expedia.ca/Bartholomews-Cobble-Sheffield.d909390908452102144.Vacation-Attraction) ## Cities near Sheffield ![Great Barrington](https://images.trvl-media.com/place/110336/0637a4e2-3fd9-47f4-811d-d18c1eac7d62.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Great Barrington ![Bear Mountain Salisbury Connecticut Landscape](https://images.trvl-media.com/place/154559/462f00fa-2a27-418e-a710-d8542c3383c3.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Salisbury ![Free Library, South Egremont, Massachusetts](https://images.trvl-media.com/place/183341/de405ed5-d4df-42fa-ada0-31aa80ee8b4b.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### South Egremont - Cities near Sheffield - Places of interest [Great Barrington](https://expedia.ca/Great-Barrington.dx110336)[Salisbury](https://expedia.ca/Salisbury.dx154559)[South Egremont](https://expedia.ca/South-Egremont.dx183341)[Ashley Falls](https://expedia.ca/Ashley-Falls.dx901768766462177280) - [National Shrine of the Divine Mercy ](https://expedia.ca/National-Shrine-Of-The-Divine-Mercy-Stockbridge.d553248621532665250.Vacation-Attraction) - [Catamount Ski Area ](https://expedia.ca/Catamount-Ski-Area-United-States-of-America.d6087211.Vacation-Attraction) - [Norman Rockwell Museum ](https://expedia.ca/Norman-Rockwell-Museum-Stockbridge.d6091839.Vacation-Attraction) - [Naumkeag Museum ](https://expedia.ca/Naumkeag-Museum-Stockbridge.d6091843.Vacation-Attraction) - [Lake Taghkanic State Park ](https://expedia.ca/Lake-Taghkanic-State-Park-Ancram.d553248634328801676.Vacation-Attraction) - [Ventfort Hall Mansion and Gilded Age Museum ](https://expedia.ca/Ventfort-Hall-Mansion-And-Gilded-Age-Museum-Lenox.d553248621532665270.Vacation-Attraction) - [Lenox Library ](https://expedia.ca/Lenox-Library-Lenox.d553248621532665268.Vacation-Attraction) ![](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. 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