Book Exclusive Sheffield Vacation Packages
Sheffield flight + hotel packages
Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Schenectady Downtown
Seward Place
per person
May 16 - May 19
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Albany (ALB)
Stay at this 4-star eco-certified hotel in Schenectady. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Rivers Casino & Resort and Museum of Innovation and Science are located nearby.
Top Sheffield hotels deals
Wilder House Berkshires
48 S Main Street, Sheffield, MA
The price is CA $218 per night
CA $218
CA $243 total
includes taxes & fees
Apr 17 - Apr 18
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.
Guesthouse Cabin vacation rentals in Berkshire County
The price is CA $719 per night
CA $719
CA $1,223 total
includes taxes & fees
Apr 14 - Apr 15
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.
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.
Life House Berkshires
194 Pittsfield Rd, Lenox, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $138 per night
CA $138
CA $154 total
includes taxes & fees
Apr 22 - Apr 23
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 $126 per night
CA $126
CA $141 total
includes taxes & fees
Apr 16 - Apr 17
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.
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
190 Meadow Street, South Lee, MA
Free cancellation
Reserve now, pay when you stay
The price is CA $153 per night
CA $153
CA $190 total
includes taxes & fees
Apr 28 - Apr 29
Stay at this 3.5-star family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business center, and a snack bar/deli. Our guests praise the helpful staff in our reviews. Popular attractions Tanglewood Music Center and Berkshire Theatre Festival are located nearby.
Pool
Air conditioning
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.
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.
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
