Book Exclusive Sheffield Vacation Packages
Sheffield flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Albany Airport
per person
Feb. 7 - Feb. 9
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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 Albany County Hockey Facility are located nearby.
The Equinox Golf Resort & Spa
Save 100% on your flight
per person
Feb. 7 - Feb. 14
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
Stay at this 4.5-star luxury hotel in Manchester. Enjoy free parking, a full-service spa, and 4 restaurants. Our guests praise the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Aspen At Manchester
per person
Feb. 7 - Feb. 14
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
Stay at this hotel in Manchester Center. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Dana L. Thompson Memorial Park and Lye Brook Falls are located nearby.
La Quinta Inn & Suites by Wyndham Latham Albany Airport
per person
Feb. 7 - Feb. 9
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Albany (ALB)
Book a stay at this 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.
Kimpton Taconic Hotel, an IHG Hotel
per person
Feb. 7 - Feb. 14
found 8 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to Albany (ALB)
Stay at this 4-star golf hotel in Manchester. Enjoy an outdoor pool, breakfast (surcharge), and room service. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Golf Club at Equinox and American Museum of Fly Fishing are located nearby.
Top Sheffield hotels deals
Race Brook Lodge
864 S Undermountain Rd, Sheffield, MA
The price is CA $246 per night
CA $246
CA $275 total
includes taxes & fees
22 Dec - 23 Dec
Stay at this hotel in Sheffield. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Mount Everett State Reservation and Drury Preserve are located nearby.
Pool
Parking included
Antique Farmhouse Totally Restored
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Mount Riga State Park and Taconic Chapel Park are located nearby.
Hot tub
Kitchen
Cheerful 3-bedroom cottage with woodstove
The price is CA $341 per night
CA $341
CA $730 total
includes taxes & fees
5 Jan - 6 Jan 2025
Stay at this vacation home in Sheffield. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Drury Preserve and Lime Kiln Farm Wildlife Sanctuary are located nearby.
Kitchen
Washer
The Red Lion Inn
30 Main Street, Stockbridge, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $186 per night
CA $186
CA $272 total
includes taxes & fees
1 Jan - 2 Jan 2025
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Schantz Galleries and Mission House are located nearby.
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $140 per night
CA $140
CA $156 total
includes taxes & fees
1 Jan - 2 Jan 2025
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 Guido's Marketplace and Bousquet Ski Area are located nearby.
Pool
Hot tub
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $128 per night
CA $128
CA $143 total
includes taxes & fees
1 Jan - 2 Jan 2025
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 Kennedy Park and Pleasant Valley Wilderness Sanctuary are located nearby.
Pet-friendly
Parking included
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.
Drury Preserve
You can take time to visit Drury Preserve during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
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.
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.Frequently asked questions
Photos of local treasures
Browse Sheffield vacation photos for more inspiration
