Sheffield Vacations from $509
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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, 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.
Urban Cowboy Lodge
Save 100% on your flight
Price was $992, price is now $730 per person
$730
per person
May 28 - May 31
found 13 hours ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
9.2/10 Wonderful! (212 reviews)
Staff was super sweet. But there should be some sort of service to take you to your room/bring you up to the main lodge for dinner. Maybe a front desk person with a golf cart. Pretty dangerous to walk down that path alone at night in the dark after some drinks at dinner. Otherwise, very chic and comfortable.
Reviewed on Mar 22, 2026
Hotel Trilogy Albany Airport, Tapestry Collection by Hilton
Price was $894, price is now $772 per person
$772
per person
Jun 19 - Jun 21
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
8.6/10 Excellent! (1,002 reviews)
Great stay. Beautiful lobby, clean room, good price, and a solid location for those families of Siena students, I highly recommend it.
Reviewed on Mar 28, 2026
Hilton Albany
Downtown Albany
Price was $712, price is now $618 per person
$618
per person
Jun 19 - Jun 21
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to Albany (ALB)
7.2/10 Good! (1,020 reviews)
The hotel has a gorgeous location, modern renovation, relatively clean. But we noticed mice in the restaurant, there were not enough towels in the pool. But I liked the staff. In general, we are satisfied with the rest
Reviewed on Apr 5, 2026
Emerson Resort & Spa
Price was $589, price is now $520 per person
$520
per person
May 28 - May 31
found 13 hours ago
Roundtrip flight included
Raleigh (RDU) to Albany (ALB)
9.4/10 Exceptional! (53 reviews)
The room is always clean and tidy. The hot tub in the room was nice as well. The staff are always nice.
Hopefully they will add more items to their stores.
I feel that the breakfast should be open longer.
Reviewed on Mar 27, 2026
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
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $170 total per night from Apr 7 to Apr 8
$170 total
Apr 7 - Apr 8
Total with taxes and fees
9.8/10 Exceptional! (44 reviews)
Only discomfort was a hard rug on my barefeet. So I'll remember to bring slippers. Otherwise, the ambiance, service, friendliness, access was wonderful. What a lovely place!
Reviewed on Apr 3, 2026
Luxury Private Estate in the Berkshires | Whitney by AvantStay
Sheffield MA
8.6/10 Excellent! (14 reviews)
Great quiet house.
Reviewed on Oct 17, 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 May 5 to May 6
$120 total
May 5 - May 6
Total with taxes and fees
9/10 Wonderful! (895 reviews)
Love that place. Does need a little sprucing up. Staff great and accomodating
Reviewed on Apr 5, 2026
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.
Find the Best Sheffield Vacation Packages
Sheffield Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 3,400 |
Max Temp Winter | 30ºF |
Max Temp Summer | 80ºF |
Top Sights | Bash Bish Falls State Park, Umpachene Falls Park and Mount Everett State Reservation |
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
