Sheffield Vacations from $357
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Sheffield vacation packages
Price found within the past 48 hours. Click for updated prices.
Aspen At Manchester
Price was $436, price is now $357 per person
$357
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
8.8/10 Excellent! (580 reviews)
Quiet, clean rooms very convenient to town center and the green mountain bluegrass festival. Would definitely stay here again.
Reviewed on Aug 15, 2025
The Equinox Golf Resort & Spa
Save 100% on your flight
Price was $557, price is now $369 per person
$369
per person
Nov 7 - Nov 10
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
7.4/10 Good! (512 reviews)
When we arrived the front desk had 2 people working with numerous check ins as there was a convention checking in as well as other guests. They were understaffed in many departments. The elevator rug needed replacement as it was dirty and worn. The side entrances were full of large spider webs and debris all the time it appeared no one every cleaned them. It was the disabled entrance. Our bathroom had a serious outdated issue. The hand rails in the tub were rusty and full of soap scum. The outside was in need of a refresh as well most of the iconic green shutters were broken/falling off. It just felt off from the beautiful iconic Equinox Inn of old when the owners took extreme pride in the quality of their quests experiences and comforts.
Reviewed on Aug 21, 2025
Hotel Brookmere & Arbor Spa
Save 100% on your flight
Price was $1,543, price is now $1,113 per person
$1,113
per person
Oct 6 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
9/10 Wonderful! (93 reviews)
Brand new Hotel and Spa. Limited staff and also limited spa availability. The staff is very nice and attentive. They need more Spa staff or one needs to book the spa at the time you book your room. Fills up fast. There are no trash cans around the facility. The menu at the restaurant is very specific. Overall great rooms. Very elegant. Would book again.
Reviewed on Aug 22, 2025
Hilton Garden Inn Saratoga Springs
Price was $1,595, price is now $1,274 per person
$1,274
per person
Oct 6 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to Albany (ALB)
8/10 Very Good! (1,009 reviews)
Shower soap dish wasnt clean - Leftoever soap want cleaned
Reviewed on Aug 24, 2025
Discover the most popular places to visit in Sheffield
Magnolia Bluffs Casino
Why not roll the dice with a visit to Magnolia Bluffs Casino during your travels in Sheffield? Discover the area's breweries or seek out the hiking trails.
Sheffield Hotel Deals
Wilder House Berkshires
48 S Main Street, Sheffield, MA
$185 nightly
The price is $207 total per night from Sep 1 to Sep 2
$207 total
Sep 1 - Sep 2
Total with taxes and fees
9.6/10 Exceptional! (29 reviews)
"Brads and Lara both served a fabulous breakfast. So friendly and welcoming! The bed was very comfortable. Only complaint was that the cabinet, closet door needs to be greased with WD 40 please on the hinges! A terrible & loud screeching noise!"
Reviewed on Aug 12, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
$108 nightly
The price is $120 total per night from Sep 7 to Sep 8
$120 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (586 reviews)
"I stayed here for a work trip to a remote project site. This place was very impressive for the money. The rooms were large and had everything. The place was clean and staff very pleasant and accommodating. I didn’t expect a lot for what I paid but was pleasantly surprised."
Reviewed on Aug 23, 2025
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
$178 nightly
The price is $199 total per night from Sep 1 to Sep 2
$199 total
Sep 1 - Sep 2
Total with taxes and fees
9/10 Wonderful! (693 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
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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Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.