Title: Sheffield Vacation Packages & Trips 2025/2026 from CA $878 | 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) ![](https://images.trvl-media.com/place/157238/14d96789-8e82-406f-8456-70392b70b95e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Sheffield Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence ### Better together Save up to CA $1,096 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.ca/Ski-Butternut-Great-Barrington.d6182072.Vacation-Attraction), [Housatonic River Walk](https://www.expedia.ca/Housatonic-River-Walk-Great-Barrington.d553248621532665241.Vacation-Attraction) and [Lake Buel](https://www.expedia.ca/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. ## Top Sheffield Vacation Deals Price found within the past 48 hours. Click for updated prices. ![La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area](https://images.trvl-media.com/lodging/16000000/15910000/15903000/15902994/5610d306_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area CA $878 per person Nov 21 - Nov 23 found 21 hours ago Roundtrip non-stop flight included Montreal (YUL) to Albany (ALB) 8.8/10 Excellent! (1,011 reviews) Property not maintained but room was comfortable and large. Room was not cleaned thoroughly and smelled of previous occupants perfume Reviewed on Oct 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YUL&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=15902994&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O7siVe4iKn0HSDr4L-bBg8HIxO1DrXVRg--NP-znMZXI) ![Crowne Plaza Albany - The Desmond Hotel by IHG](https://images.trvl-media.com/lodging/1000000/40000/37100/37096/97171d33_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Crowne Plaza Albany - The Desmond Hotel by IHG CA $895 per person Nov 21 - Nov 23 found 21 hours ago Roundtrip non-stop flight included Montreal (YUL) to Albany (ALB) 9.2/10 Wonderful! (1,009 reviews) I dont have much to stay,i arrived later in the night and left at check out. Reviewed on Oct 9, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YUL&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37096&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O7siVe4iKn0HSDr4L-bBg8FqePzAuJVN_Hty_DljTfve) ![The Landing Hotel at Rivers Casino & Resort](https://images.trvl-media.com/lodging/20000000/19100000/19093300/19093277/146e5c0f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Landing Hotel at Rivers Casino & Resort Stockade Historic District CA $973 per person Nov 21 - Nov 23 found 21 hours ago Roundtrip non-stop flight included Montreal (YUL) to Albany (ALB) 9.2/10 Wonderful! (1,006 reviews) It was good. Parking was a little confusing. Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YUL&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19093277&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O7siVe4iKn0HSDr4L-bBg8EActYslNHqcz8BmG1rjZ3y) ![Hampton Inn Albany-Wolf Road (Airport)](https://images.trvl-media.com/lodging/1000000/10000/700/698/61f54404_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn Albany-Wolf Road (Airport) CA $915 per person Nov 21 - Nov 23 found 21 hours ago Roundtrip non-stop flight included Montreal (YUL) to Albany (ALB) 8.6/10 Excellent! (1,026 reviews) The is very friendly and greeted me like an old friend coming for a visit. The room was clean. Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YUL&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=698&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O7siVe4iKn0HSDr4L-bBg8F8qmH2RdbGWbIIXQQYL2lA) ![Marriott Albany](https://images.trvl-media.com/lodging/1000000/20000/11000/10979/1856b3b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Marriott Albany CA $909 per person Nov 21 - Nov 23 found 21 hours ago Roundtrip non-stop flight included Montreal (YUL) to Albany (ALB) 8.2/10 Very Good! (706 reviews) Easy and friendly check in and clean Reviewed on Oct 10, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2025-11-21/2025-11-23/?FromAirport=YUL&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=10979&paandie=true&dealMarker=6CuNs0vxu2uILjtBFDt_O7siVe4iKn0HSDr4L-bBg8FY3sCINifHzMSRpz3RT5YC) ## Ready to book your vacation to Sheffield? Choose your dates ## 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 Fully refundableReserve now, pay when you stay CA $225 CA $252 total Nov 10 - Nov 11 includes taxes & fees 9.6/10 Exceptional! (36 reviews) "Clean room comfortable bed" Reviewed on Oct 9, 2025 [](https://expedia.ca/Hotel-Search?startDate=10%2F11%2F2025&endDate=11%2F11%2F2025&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 CA $575 CA $1,002 total Oct 26 - Oct 27 includes taxes & fees 10/10 Exceptional! (9 reviews) "This was exactly what we were looking for. The property was magnificent the cabin cozy, fully stocked. We plan on coming back soon." Reviewed on Aug 27, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&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 9.8/10 Exceptional! (58 reviews) "The property was beautiful. Very spacious, inside and out." Reviewed on Aug 17, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=24%2F10%2F2025&endDate=25%2F10%2F2025&selected=27129515&PinnedHotelID=27129515&HadPinnedHotel=true®ionId=157238) [](https://expedia.ca/Hotel-Search?startDate=24%2F10%2F2025&endDate=25%2F10%2F2025&selected=27129515&PinnedHotelID=27129515&HadPinnedHotel=true®ionId=157238) [See all 1,256 properties in Sheffield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025®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. ![](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.ca/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.ca/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) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* 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 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 ![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAE/ElEQVR4Xu3cPXIbORBAYbAUMNwjzFHmaODReBQeYUMGKmPdP0BjQEqlLpc3IN9LTPUA+CZDUfZuaf9DZR38jUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSakI+y9Im00v5p/3ywbTq1Nq1r/o9qu1fXzOqcTIICAiItckUBARkQWr81Bxptn1vd/ljnKjI2RbEaHQ8CwQEBEQCidEIBMTXamdDnp/4pLFK840jkCUQkAIC4oEsgfja8vsrdnNEfvqQb92aXvut3eQzCEgBAfFACghI+TOk2Yl9uy+8dNdP1EA2mV4KiK9uICAgIAXkp0g0Ib2xSl9F73hPRqdpM0gBAQFZH4BYIAVkRY5t/cST3N5nc78eLdU4GeTJaKnGySBPRks1TgZ5MlqqcTLIk9FSjZNBnoyWapwM8mS0VOPkCfkq3a4Xuvw0v8rZFijyXSAgXwUSgYB8FUj0yoj+p0y/t8sf+rfJ8ets+aCI/wdPitxk1egu820aSCAgHogFAhKBgDQ50f82ed4+f5+e222PrpJXUbfIqxxdEG23PSAgFgiIB1LeHplvb22TUW1+7R87jW23abq3+/gsGz0QEJBpClIbyFgBAnJAzjLw2ztOHK7/0ttHbbrjzzIqP7vjQUBApkBAQOSP90W0u3zW5hPFjdHIX6XnZ1XbIYHMgYBIfla1HRLIHAiI5GdV2yG9LqLtgoy5/4Zb22J501cRVxG943eZyrqPwzoQDQQEpAcSgWhvjbSx1tu6e+qLrdr8jj9PG+e2MbdANBAQf2RtY26BaCAg/sjaxtx6VWTtU07Uv2DebXDr55zk2ndEX8Xf7jy9yggE5EkgIDYA+S6Qd0D0RP0+bU/6Wr3Qx7duPXFG9Ct2W659fzsPBAQERJ+AjLNGICBt+or9sF0R6WN8n97lYSlbf7uebCwgdgRIBALSQED0RBBZFB+bbe+3t2zXfLuO5mZ3fZUCAgKigVwKCAiIV+PYCfmUR8c7PtaqKyM/8eSbxip/lcg3SiAgILYK5DatBdFAQJrc8Yrs+qRs4s7bB6KpK6s83XiXVWsgDQTEAwFZAmlvj3zaSSff7qPafHuTE489IDp6DEQDAbFVILWBRCDauyM1furbL3bebiNtXPuKFLv2daR3/Fg1AtFAIpBeHSeB2AeQCKRXx0kvjMTaMddfZ1/7iZp+EVektZshmq/alhcGAQEBAQEB+RpZ+xh3/DH//1/KfjtxpO4ayNgPEoEsgYz9IBHI0ksiT/pcr/2buYpcp7Orrb8aoqumQBrIYyAgIBJIe3vkc9qkbR05yeO7DRXRdtt2k8++6mpPtjhUAykgtiICAWkgGkgBkbXRtPaXn+husTt+uIpojuirTIFoIBEICEgPRAPR79OlnKcT9V9cjxNj+9UGD7V2AwGRQBoIyBKIPAZpP0BqLAg3/n2XjJp869bRLq8yzop98RFEnoCAgPRAQECeIM22a7FdOvkdP3ZrV9uo1RiDgIBMgYCAgDwgkSPN3L2Pv0X0VUBAPBAQkEMgIDE8Isc2mV7s827bN1s1f8UeqXuO8yIQEJAeSAM5BgLy9wJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIqtdB/gM8vbwyW+epFgAAAABJRU5ErkJggg==)