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.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
Price was CA $1,318, price is now CA $1,134 per person
CA $1,134
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
9/10 Wonderful! (579 reviews)
Enjoyed the room, towels and kitchen. I can recommend.

Reviewed on Aug. 18, 2025

Prospect Berkshires

Prospect Berkshires

3 out of 5
Price was CA $2,478, price is now CA $1,747 per person
CA $1,747
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
9/10 Wonderful! (2 reviews)
Prospect was a wonderful stay with very friendly staff. The property is very well maintained. We had a great time with the all the lake activities. Would definitely recommend for a quick getaway

Reviewed on Jun. 23, 2025

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

Secluded w/ Deck Views, Hot Tub, & Ping Pong Hudson in the Berks by Avantstay

3 out of 5
Price was CA $3,561, price is now CA $2,995 per person
CA $2,995
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
No reviews
Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
Price was CA $1,367, price is now CA $1,199 per person
CA $1,199
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
8.6/10 Excellent! (1,957 reviews)
If your hiking Mt Greylock this is a fantastic location. We arrived late and left early so we didn't get to use anything on the property but it did look at nice place for families to stay it. We did sit by the outdoor fire pit for a while which was cool.

Reviewed on Aug. 21, 2025

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
Price was CA $1,424, price is now CA $1,250 per person
CA $1,250
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
9/10 Wonderful! (697 reviews)
Handicap accessible

Reviewed on Aug. 22, 2025

Ready to book your vacation to Sheffield?

 

Choose your dates

Sheffield Hotel Deals

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! (583 reviews)
Satisfied customer
"as good as the last time we stayed there."

Reviewed on Aug. 21, 2025

Berkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Sep 1 to Sep 2
CA $222
CA $248 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (692 reviews)
"We needed a place to stay in the area Found the place cutely decorated and was happy there was a restaurant on premise"

Reviewed on Aug. 21, 2025

Berkshires Untold
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is CA $128 per night from Sep 7 to Sep 8
CA $128
CA $143 total
Sep 7 - Sep 8
includes taxes & fees
8.2/10 Very Good! (1,001 reviews)
"nice place"

Reviewed on Aug. 18, 2025

Quality Inn
See all 1,256 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 $1,134 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.