Sheffield Vacations from $464
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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.
The Equinox Golf Resort & Spa
Save 100% on your flight
Price was $826, price is now $549 per person
$549
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
7.4/10 Good! (567 reviews)
We feel that the resort fee to access the pool and hot tub as well as the other services covered are over priced. We stay at resorts and hotels all over the US and you are the ONlY place that charges for this.
Reviewed on Nov 21, 2025
Hotel Brookmere & Arbor Spa
Price was $881, price is now $589 per person
$589
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.2/10 Wonderful! (218 reviews)
The place was fantastic in every way, clean, great service, beautiful location and close to everything you want to do in and around Saratoga Springs. I will book this beautiful spot again!
Reviewed on Dec 1, 2025
Lodges At Cresthaven
Price was $896, price is now $668 per person
$668
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
9.4/10 Exceptional! (531 reviews)
Staff were awesome . The owners are the greatest people . Their son went above and beyond for us. Our view and room was unbelievable. The boathouse is so inviting, great opportunity to meet people, and food outstanding. John the bartender is the best!!! Highly recommend this place !!!
Reviewed on Nov 23, 2025
Aspen At Manchester
Save 100% on your flight
Price was $817, price is now $641 per person
$641
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
Miami (MIA) to Albany (ALB)
8.8/10 Excellent! (600 reviews)
Great location
Everything updated
Pleasant greeting in lobby
Reviewed on Nov 25, 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
Fully refundableReserve now, pay when you stay
$155 nightly
The price is $174 total per night from Dec 8 to Dec 9
$174 total
Dec 8 - Dec 9
Total with taxes and fees
9.6/10 Exceptional! (38 reviews)
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!
Reviewed on Nov 10, 2025
Antique Farmhouse Totally Restored
Sheffield MA
9.6/10 Exceptional! (60 reviews)
Our group of 8 had a delightful stay at the Antique Farmhouse! Robin was very friendly and responsive. It’s a large house, with plenty of room to spread out and explore. The kitchen is large, and very well equipped. We enjoyed cooking meals together as a group. The property itself is beautiful, and ...
Reviewed on Oct 16, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$120 nightly
The price is $135 total per night from Dec 7 to Dec 8
$135 total
Dec 7 - Dec 8
Total with taxes and fees
9/10 Wonderful! (768 reviews)
When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it.
Reviewed on Nov 26, 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.
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.