
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.


Prospect Berkshires
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


Vacation Village in the Berkshires
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
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
Sheffield Hotel Deals

Berkshire Mountain Lodge
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

Berkshires Untold
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

Quality Inn
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
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.
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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.