Title: Sheffield Vacation Packages & Trips 2025/2026 from CA $1,007 | 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

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    Plan, book, travel with confidence
    

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Better together

Save up to CA $1,096 when you book a flight and hotel together\*

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Find the right fit

With over 300,000 hotels worldwide, it's easy to create a perfect package

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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.

![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/e8f22f38_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Cornell Inn, Lenox & The Berkshires

CA $1,007

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

9/10 Wonderful! (1,003 reviews)

Very nice place. Quiet. The breakfasts are included and are upscale with excellent staff service. Unless you are young and don't care, make sure you get a ground floor room - the upstairs rooms require a walk up a large staircase, and are inconvenient. Would definitely return.

Reviewed on Sep 5, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-16/?FromAirport=YYZ&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=1634230&paandie=true&dealMarker=ergcRkbvQ132oav0knEnnKGDj2YXJN-XLIfDCcgA8oHyIr_TXamLO18izx-KiGgS)

![The Equinox Golf Resort & Spa](https://images.trvl-media.com/lodging/3000000/2760000/2759100/2759006/0d30b96a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Equinox Golf Resort & Spa

CA $1,269

per person

Nov 20 - Nov 23

found 23 hours ago

Roundtrip flight included

Halifax (YHZ) to Albany (ALB)

7.4/10 Good! (529 reviews)

The staff was wonderful. I did request early check in but was informed that could not be guaranteed. When I arrived to check in, I was told that they didn’t see the request for early check in. I provided a copy of that very message saying it couldn’t be guaranteed.

Reviewed on Sep 30, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-20/2025-11-23/?FromAirport=YHZ&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2759006&paandie=true&dealMarker=tDrkEYJ_kO0Swe42O5f4xtO8w6pIRiMuBOkSCdCIrgBNFLG0JhZMVqEy3iiIl4FT)

![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 $1,124

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

9.2/10 Wonderful! (1,006 reviews)

We came to hotel after complicated driving for 7 hours tired and were met by friendly staff. Check in was fast and easy. After all we got excellent warm chocolate cookies. Love the hotel !!

Reviewed on Sep 13, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-20/2025-11-25/?FromAirport=YYZ&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19093277&paandie=true&dealMarker=quvvVXrBkDDtrS4cIWqVo37dhqyg72ULgos0vXu0bVbfyhrfq6CiQUp3px9iJhg4)

![Gedney Farm](https://images.trvl-media.com/lodging/42000000/41180000/41178000/41178000/6d6c1dc1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Gedney Farm

CA $1,044

per person

Nov 14 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

9.2/10 Wonderful! (129 reviews)

Gedney Farms is very quiet, peaceful and rustic. Your stay is in a converted barn with towering ceilings, hard wood floors, and rustic reused furniture with no TV phones or radios. Note some rooms require stair climbing on winding stairs with sections without rails or handholds. Some bathtubs are very high. It would be helpful to talk to the location about the room accommodations if mobility is an issue. The staff is very unobtrusive almost to the point of non existent. The breakfast was fresh and healthy with plain Greek yogurt, granola, fresh fruits, hard boiled eggs, muffins and bread to toast. The grounds are well tended but not fussy and offer beauty, peace and quiet. The location is an easy 30 minutes to Tanglewood and 15 minutes to Stockbridge. It is nearby Berkshire Botanical Gardens, Dr. Suess Museum, WEB DuBois statue and homestead, Norman Rockwell museum, Monument mountain, Housatonic river and many art stores, general stores, outdoor activities. This area is car dependent.

Reviewed on Aug 12, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-14/2025-11-16/?FromAirport=YYZ&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=41178000&paandie=true&dealMarker=ergcRkbvQ132oav0knEnnKGDj2YXJN-XLIfDCcgA8oEM1rWLBPbxOnuoe-EAhOLI)

![Hyatt Place Albany/Downtown](https://images.trvl-media.com/lodging/93000000/92790000/92787800/92787704/b91f3040_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hyatt Place Albany/Downtown

Downtown Albany

CA $1,066

per person

Nov 20 - Nov 25

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Albany (ALB)

9/10 Wonderful! (1,186 reviews)

nice new hotel in the heart of downtown Albany

Reviewed on Sep 30, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-20/2025-11-25/?FromAirport=YYZ&Destination=ALB&NumRoom=1&NumAdult=2&NumChild=0&hotelId=92787704&paandie=true&dealMarker=quvvVXrBkDDtrS4cIWqVo37dhqyg72ULgos0vXu0bVarpHwzKCFLdHfuIRmg9OZF)

## 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)

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Wilder House Berkshires

48 S Main Street, Sheffield, MA

CA $226

CA $253 total

Nov 2 - Nov 3

includes taxes & fees

9.6/10 Exceptional! (35 reviews)

"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."

Reviewed on Sep 25, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=105813835&PinnedHotelID=105813835&HadPinnedHotel=true&regionId=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)

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Guesthouse Cabin vacation rentals in Berkshire County

Sheffield

CA $514

CA $967 total

Oct 5 - Oct 6

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=05%2F10%2F2025&endDate=06%2F10%2F2025&selected=99962392&PinnedHotelID=99962392&HadPinnedHotel=true&regionId=157238)

![Antique Farmhouse Totally Restored ](https://images.trvl-media.com/lodging/28000000/27130000/27129600/27129515/46c8a41a_y.jpg?impolicy=resizecrop&rw=340&ch=150)

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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=16%2F10%2F2025&endDate=17%2F10%2F2025&selected=27129515&PinnedHotelID=27129515&HadPinnedHotel=true&regionId=157238)

[](https://expedia.ca/Hotel-Search?startDate=16%2F10%2F2025&endDate=17%2F10%2F2025&selected=27129515&PinnedHotelID=27129515&HadPinnedHotel=true&regionId=157238)

[See all 1,258 properties in Sheffield](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025&regionId=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)

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\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.

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![QR code to download the app](data:image/png;base64,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)