Sheffield Vacation Packages

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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, Housatonic River Walk and Lake Buel, 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 Wiltwyck

The Wiltwyck

3.5 out of 5
per person
Oct 22 - Oct 26
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.4/10 Exceptional! (152 reviews)
Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

Relax in Style at Historic Modern on Main With Modern Amenities & Wooded Views

3 out of 5
per person
Oct 22 - Oct 26
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
No reviews
Kingston Carriage House

Kingston Carriage House

4 out of 5
Roundout
per person
Oct 22 - Oct 26
found 6 hours ago
Roundtrip flight included
Toronto (YYZ) to Albany (ALB)
9.2/10 Wonderful! (19 reviews)
I liked the record player and the room was clean and comfy. Coffee and pastries were waiting by the door in the morning. Checking in, the battery was dead in the room lock. Had to wait 30 mins for service to arrive. The shower floor was dangerously slippery! An accident waiting to happen. Was unable to connect to Wi-Fi after multiple tries.

Reviewed on Aug. 3, 2025

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Sheffield Hotel Deals

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street, Sheffield, MA
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Sep 9 to Sep 10
CA $221
CA $247 total
Sep 9 - Sep 10
includes taxes & fees
9.6/10 Exceptional! (28 reviews)
"My sister and I and her husband had a very nice stay. The rooms are very nice and very clean. We enjoyed an excellent breakfast every morning. I highly recommend Wilder House!"

Reviewed on Jul. 30, 2025

Wilder House Berkshires
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield
9.8/10 Exceptional! (56 reviews)
"It was a fun place for a lot of people to stay. The only negative was the owner not having the air conditioning units in the windows of the bedrooms especially since it was so hot."

Reviewed on Jul. 14, 2025

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Antique Farmhouse Totally Restored
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is CA $106 per night from Sep 7 to Sep 8
CA $106
CA $149 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (543 reviews)
"Very spacious room with full kitchen. Definitely worth the price. Would use again"

Reviewed on Aug. 5, 2025

Berkshire Mountain Lodge
See all 1,265 properties in Sheffield
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.
All Inclusive Vacations
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Frequently asked questions

How much does a Sheffield vacation package cost?
Offering great value package deals from CA $887 on Expedia, you'll be surprised at how little a vacation to Sheffield costs! Expedia's packages make travel planning easier and save you more.
What are the cheapest months to go to Sheffield?
The off-season is the best time to visit Sheffield if you're on a budget. Another tip for scoring cheap Sheffield vacation packages? Try to avoid visiting during public holidays and any major events.
How many days is enough for Sheffield?
Usually, a handful of days is enough to explore the major sights during your Sheffield vacation. But if you'd like to have some time to unwind or go on day tours, consider extending your itinerary.
How to find the best Sheffield package deals?
Begin your search for a Sheffield package deal by entering your preferred trip dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with unbeatable savings. If you don't find the perfect Sheffield package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Sheffield escape underway.
Is it cheaper to book a Sheffield vacation as a package?
You can enjoy significant savings on your Sheffield getaway by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to browse some great flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Sheffield?
Land incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Sheffield vacation.
How to plan a trip to Sheffield?

  1. Choose the right time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to travel to Sheffield.
  2. Work out your budget: Make sure you have enough money to pay for everything from food and transportation to activities and flights. Your accommodations will probably be the biggest expense during your trip to Sheffield.
  3. Decide your trip length: Think about how long you'd like to spend discovering Sheffield. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left is to pick a Sheffield vacation package that brings all your bookings together.

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