Title: Sheffield Vacation Packages 2026 from $341 | Expedia.com [Sheffield Travel Guide](https://expedia.com/Sheffield.dx157238)[Hotels in Sheffield](https://expedia.com/Sheffield-Hotels.d157238.Travel-Guide-Hotels)[Vacation Rentals in Sheffield](https://expedia.com/Sheffield-Vacation-Rentals.d157238.Travel-Guide-VacationRentals)[Flights to Sheffield](https://expedia.com/Cheap-Flights-To-Sheffield.d157238.Travel-Guide-Flights)[Car Rentals in Sheffield](https://expedia.com/Car-Rentals-In-Sheffield.d157238.Car-Rental-Guide) ![](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Sheffield Vacations from $341 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place ## Your Sheffield Vacation The stress-free way to experience this unique city is with a custom-made Sheffield vacation package. Stay in the neighborhood of Canann Village Historic District, which is great for dining, culture and shopping or go someplace else — our package deals are all about you. Fill your free time with visits to [Ski Butternut](https://www.expedia.com/Ski-Butternut-Great-Barrington.d6182072.Vacation-Attraction), [Housatonic River Walk](https://www.expedia.com/Housatonic-River-Walk-Great-Barrington.d553248621532665241.Vacation-Attraction) and [Lake Buel](https://www.expedia.com/Lake-Buel-Great-Barrington.d553248635976196476.Vacation-Attraction), some of the things you really should see during a trip to Sheffield. Don't delay exploring this city any longer. Your ultimate Sheffield vacation is only a few clicks away with Expedia. ## The Latest Sheffield vacation packages Price found within the past 48 hours. Click for updated prices. ![Saratoga Casino Hotel](https://images.trvl-media.com/lodging/15000000/14720000/14710900/14710814/991e526b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Saratoga Casino Hotel $341 per person Apr 3 - Apr 5 found 13 hours ago Roundtrip flight included New York (NYC) to Albany (ALB) 9.2/10 Wonderful! (1,001 reviews) Clean room and facility. Friendly staff Reviewed on Feb 6, 2026 ![The Perch Hotel](https://images.trvl-media.com/lodging/114000000/113610000/113605400/113605320/3e266811_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Perch Hotel $766 per person Apr 9 - Apr 13 found 8 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Albany (ALB) 9.4/10 Exceptional! (22 reviews) This place is great!! Awesome view with a pool table and fireplace in the common area. Very home feeling with the decor, place was clean and tidy. Reviewed on Jan 3, 2026 ![The Old Catskill Game Farm Inn](https://images.trvl-media.com/lodging/41000000/40210000/40200900/40200828/71cf031c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Old Catskill Game Farm Inn $3,201 per person Apr 9 - Apr 13 found 8 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Albany (ALB) 9.6/10 Exceptional! (26 reviews) This Inn was amazing. We booked the Giraffe room for the weekend, and it was a great escape. Our room was super clean, a large jacuzzi tub, and very private. There was also a sauna room, gourmet kitchen, pantry with another stove, refrigerator, dish washer, fully stock with plates, and utensils. Additionally, there is a coffee bar and mini fridge stocked with bottled water. There is also a large common area with several leather sofa, and plenty of games. Another great feature is there is a bar area with a wine fridge. Shawn was amazing, he was very attentive and accommodating, he was right out front to greet us on arrival and gave a tour of the Inn. The decor was very nostalgic with decor from the original Catskill Game Farm. It was a great stay and looking forward to returning again. Reviewed on Jan 19, 2026 ![Hutton Brickyards Riverfront Hotel + Venue](https://images.trvl-media.com/lodging/67000000/66350000/66348200/66348162/w1300h849x0y2-4df25125_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hutton Brickyards Riverfront Hotel + Venue $998 per person Apr 9 - Apr 13 found 8 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Albany (ALB) 8.8/10 Excellent! (93 reviews) This was our 1st time at Hutton Brickyards, it was amazing! The staff was so nice and accommodating. The room and the amenities were amazing. We will definitely be back. Reviewed on Feb 2, 2026 ![Pocketbook Hotel and Bath](https://images.trvl-media.com/lodging/118000000/117880000/117877800/117877797/w4500h2996x0y0-b2a7729b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pocketbook Hotel and Bath $1,058 per person Apr 9 - Apr 13 found 8 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Albany (ALB) 8.8/10 Excellent! (3 reviews) The room was modern, clean, and perfect for two. I highly recommend the hotel if you are visiting Hudson. Unfortunately the Expedia picture and description did not match what was actually booked. This was not the fault of the hotel as their website accurately depicted the booking. Expedia needs to do better.... Reviewed on Feb 3, 2026 Don't see what you're looking for? See all available trips from Columbus to Sheffield [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-07/2026-03-14/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Sheffield #### 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.com/Magnolia-Bluffs-Casino-Sheffield.d553248621532644877.Vacation-Attraction) ## Sheffield Hotel Deals ![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 $186 nightly $207 total Feb 8 - Feb 9 Total with taxes and fees 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.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%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 $616 nightly $688 total Feb 8 - Feb 9 Total with taxes and fees 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.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%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 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.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=27129515&PinnedHotelID=27129515&HadPinnedHotel=true®ionId=157238) [](https://expedia.com/Hotel-Search?startDate=2%2F21%2F2026&endDate=2%2F22%2F2026&selected=27129515&PinnedHotelID=27129515&HadPinnedHotel=true®ionId=157238) [See all 1,272 properties in Sheffield](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F8%2F2026&endDate=2%2F9%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. ## Find the Best Sheffield Vacation Packages ## Sheffield Essential Information | Language | English | | --------------- | ---------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Population | 3,400 | | Max Temp Winter | 30ºF | | Max Temp Summer | 80ºF | | Top Sights | [Bash Bish Falls State Park](https://www.expedia.com/Bash-Bish-Falls-State-Park-South-Egremont.d637217608890609664.Vacation-Attraction), [Umpachene Falls Park](https://www.expedia.com/Umpachene-Falls-Park-Southfield.d553248621560926710.Vacation-Attraction) and [Mount Everett State Reservation](https://www.expedia.com/Mount-Everett-State-Reservation-South-Egremont.d637217493551992832.Vacation-Attraction) | ## More vacations you might like ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Sheffield vacation package cost? ### What are the cheapest months to go to Sheffield? ### How many days is enough for Sheffield? ### How to find the best Sheffield package deals? ### Is it cheaper to book a Sheffield vacation as a package? ### When to book a vacation package to Sheffield? ### Does Expedia offer Book Now, Pay Later Sheffield vacation packages? \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save even more - get up to 20% on select hotels 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