Sheffield Vacations from $603
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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.
The Latest Sheffield vacation packages
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Price was $741, price is now $603 per person
$603
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
9/10 Wonderful! (858 reviews)
this has been absolutely amazing and incredible for incredibly difficult time for our family because of family medical emergency. everyone has been so amazing and beautiful and healing for our loved ones and we are grateful to be close to then
Reviewed on Apr 1, 2026
The Perch Hotel
Price was $1,069, price is now $712 per person
$712
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
9.6/10 Exceptional! (28 reviews)
Such an amazing stay at the Perch - beautiful place with spacious rooms and a super cozy vibe. We felt right at home upon arrival and can’t wait to venture back again in the near future. Definitely recommend staying here!!
Reviewed on Feb 21, 2026
Hotel Brookmere & Arbor Spa
Price was $780, price is now $625 per person
$625
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
9.2/10 Wonderful! (278 reviews)
Located by the elevator was a bit noisy. Other than that, wonderful stay!
Reviewed on Mar 11, 2026
Prospect Berkshires
Price was $1,383, price is now $1,112 per person
$1,112
per person
May 21 - May 24
found 1 day ago
Roundtrip non-stop flight included
Minneapolis (MSP) to Albany (ALB)
9.8/10 Exceptional! (23 reviews)
The cabins are brand new, the property is gorgeous, restaurant features local and quality product and the staff is very responsive via text message. The lakeside sauna is private and easy to reserve. Great place!
Reviewed on Feb 20, 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
$148 nightly
The price is $166 total per night from Apr 29 to Apr 30
$166 total
Apr 29 - Apr 30
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! (15 reviews)
We had a lovely stay. Wonderfully located and well provisioned! Would happily stay here again!
Reviewed on Mar 29, 2026
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 7 to May 8
$120 total
May 7 - May 8
Total with taxes and fees
9/10 Wonderful! (896 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 |
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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.
