Book Exclusive Sheffield Vacation Packages
Sheffield flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
The Clocktower Hotel at Century House, Ascend Hotel Collection
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
Book a stay at this business-friendly hotel in Cohoes. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Colonie Center Mall and Latham Farms are located nearby.
Hilton Garden Inn Albany Airport
per person
Jul 2 - Jul 7
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Latham. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Colonie Center Mall and Crossgates Mall are located nearby.
La Quinta Inn & Suites by Wyndham Clifton Park/Saratoga Area
per person
Jul 2 - Jul 7
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Clifton Park. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Regal Clifton Park and Clifton Common are located nearby.
La Quinta Inn & Suites by Wyndham Latham Albany Airport
per person
Jul 2 - Jul 7
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
Stay at this 3-star business-friendly hotel in Latham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the clean rooms in our reviews. Popular attractions Colonie Center Mall and Curtain Call Theater are located nearby.
Hampton Inn Schenectady Downtown
Seward Place
per person
Aug 22 - Aug 25
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
Stay at this hotel in Schenectady. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Rivers Casino & Resort and Proctors Theater are located nearby.
Top Sheffield hotels deals
Wilder House Berkshires
48 S Main Street, Sheffield, MA
The price is CA $211 per night
CA $211
CA $236 total
includes taxes & fees
Jun 10 - Jun 11
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary are located nearby.
Breakfast included
Parking included
Guesthouse Cabin vacation rentals in Berkshire County
The price is CA $726 per night
CA $726
CA $1,236 total
includes taxes & fees
Jun 29 - Jun 30
Stay at this cabin in Sheffield. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Mount Everett State Reservation and Plaintain Pond are located nearby.
Kitchen
Pet-friendly
Berkshires Untold
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $234 per night
CA $234
CA $262 total
includes taxes & fees
Jun 11 - Jun 12
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Kennedy Park are located nearby.
Pet-friendly
Parking included
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $178 per night
CA $178
CA $199 total
includes taxes & fees
Jun 2 - Jun 3
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $128 per night
CA $128
CA $143 total
includes taxes & fees
Jun 12 - Jun 13
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
Breakfast included
Parking included
The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $176 per night
CA $176
CA $197 total
includes taxes & fees
Jun 4 - Jun 5
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular attractions Tanglewood Music Center and Berkshire Mountain Country Store are located nearby.
Breakfast included
Pet-friendly
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.
Popular places to visit
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.
Ashley House
You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.
Lime Kiln Farm Wildlife Sanctuary
You can take time to visit Lime Kiln Farm Wildlife Sanctuary during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
Sheffield Vacations
A smooth, hassle-free escape starts with being aware of a thing or two about your destination. It's time to acquaint yourself with a few basic facts about Sheffield!
If you venture 20 miles (32 kilometers) southeast of Hudson, or 25 miles (40 kilometers) northwest of Torrington, you'll be in Sheffield.
Ready to meet some of the locals? 3,000 people call this part of The Berkshires home.
Hotels in Sheffield
Be the early bird that catches the worm when it comes to booking your accommodations in Sheffield. With 3 places to stay, your choice is limited. Start browsing and book a comfortable room today!The Windflower Inn and The Egremont Village Inn are some of Travelocity's top accommodation options in the Sheffield region.
Places to visit in Sheffield
If you've got an inquisitive mind, it's worth a trip to Ashley House. You never know what you could encounter here! Need more options? Love nature so much that you could hug a tree? Be sure to stop and throw your arms around one of the fine specimens at Questing. You'll have an abundance to pick from! And that's not all. Add some extravagance to your break with a side trip to Les Trois Emme Winery. Stop off at the winery, book a guided tour and try a taste of the finished product!Where do you fly into for Sheffield?
Prepare for some awesome adventures in Sheffield. Once you've left Bradley International Airport (BDL), the downtown area will be just 35 miles (56 kilometers) to the west.Photos of local treasures
Browse Sheffield vacation photos for more inspiration
