Sheffield Vacations 2026

Top Sheffield hotels deals

Wilder House Berkshires

48 S Main Street Sheffield MA

Free cancellation

Reserve now, pay when you stay

CA $230

CA $257 total

Oct 28 - Oct 29

includes taxes & fees

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

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

8 Dan Fox Dr Pittsfield MA

Free cancellation

Reserve now, pay when you stay

CA $119

CA $165 total

Nov 10 - Nov 11

includes taxes & fees

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

461 Pittsfield Rd Lenox MA

Free cancellation

Reserve now, pay when you stay

CA $134

CA $149 total

Nov 1 - Nov 2

includes taxes & fees

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 Great Barrington

372 Main Street Great Barrington MA

Free cancellation

CA $105

CA $118 total

Nov 22 - Nov 23

includes taxes & fees

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

Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires

190 Meadow Street South Lee MA

Free cancellation

CA $175

CA $223 total

Nov 1 - Nov 2

includes taxes & fees

Book a stay at this ski 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

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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.