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Top Sheffield hotels deals

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
48 S Main Street Sheffield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $267 per night
CA $267
per night
Sep 13 - Sep 14
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
Antique Farmhouse Totally Restored

Antique Farmhouse Totally Restored

Sheffield MA
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Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Mount Riga State Park and Taconic Chapel Park are located nearby.
Hot tub
Kitchen
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Free cancellation
Reserve now, pay when you stay
The price is CA $110 per night
CA $110
per night
Oct 1 - Oct 2
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $144 per night
CA $144
per night
Sep 22 - Sep 23
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
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Free cancellation
Reserve now, pay when you stay
The price is CA $194 per night
CA $194
per night
Sep 28 - Sep 29
Stay at this 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
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

2.5 out of 5
1055 South Street Pittsfield MA
Free cancellation
The price is CA $175 per night
CA $175
per night
Sep 13 - Sep 14
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Tanglewood Music Center and Guido's Marketplace are located nearby.
Pool
Hot tub
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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.

Stay near popular Sheffield attractions

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.
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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

How much are vacation packages to Sheffield?
You'll be surprised — you can recharge your batteries in Sheffield for a paltry . Here at Travelocity, we save you money and time with our excellent vacation packages. With experiences, hotels and flights all available at our one-stop shop, what are you waiting for?
How long should my Sheffield vacation be?
Around 2 nights is the average time frame visitors vacation in Sheffield. But how long is right for you depends on how many treasured memories you want to create. Why not stay a bit longer and explore some hidden gems?
Where can I get the best vacation package deals for Sheffield?
Snapping up the perfect package deal to Sheffield is a cinch with Travelocity. With 400 air carriers and 1,000,000 properties across the globe, the choice is yours when selecting your hotels and flights.
Why should I book my Sheffield vacation bundle via Travelocity?
We offer round-the-clock support, exceptional service and a Price Match Guarantee. Life is all about the journey — and we have exciting destinations for you to journey to all across the world. Roam with us and your bank balance will thank you for it.
Can I save on my Sheffield car rental if I book it with hotels and flights?
You certainly can — bundle your flight, hotel and car into a Sheffield vacation package and you'll save a ton. With so much to discover in Sheffield, having your own set of wheels will make it easy to explore. Once you've buckled yourself in, hit the wide open road and make tracks to Times Square, a famous sight approximately 161 kilometers from Sheffield.
Which airport is best for Sheffield?
Bradley Intl. Airport (BDL) is one of the best airports for Sheffield. You'll find it 56 kilometers east of the buzzing city center. Your other choices are Albany Intl. Airport (ALB) (80 kilometers away from central Sheffield) and Stewart Intl. Airport (SWF) (88 kilometers away from central Sheffield).
What is there to do in Sheffield?
While hopping off the tourist trail can be rewarding, you shouldn't ignore the well-known sights that make a destination famous. Magnolia Bluffs Casino and Ashley House are a couple of them in Sheffield.
Where should I stay when visiting Sheffield?
The Built in 1739, near Appalachian Trail & River, 7 Min. From Great Barrington is popular with many travelers. Book as soon as possible before it's too late.

Photos of local treasures

Browse Sheffield vacation photos for more inspiration

A covered wooden structure with a sloped roof, surrounded by greenery and trees.
A wooden covered bridge with a gabled roof, surrounded by trees and a body of water.