Hotels in Sheffield

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Check prices for these dates

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Where to stay in Sheffield?

Wilder House Berkshires Room 3 | Premium bedding, individually decorated, individually furnished
Wilder House Berkshires
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (41)
  • cleanliness
    Stay at a charming Sheffield B&B with a convenient weekend breakfast service.
The price is $162
$181 total
includes taxes & fees
Dec 30 - Dec 31
Wilder House Berkshires
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.
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Budget hotels in Sheffield and vicinity

Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (810)
The price is $67
$74 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Monument Mountain Motel
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.
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Top landmarks in Sheffield

Ashley House

If you're planning a bit of sightseeing during your trip, head to Ashley House— just one of the landmarks located 3.5 mi (5.6 km) from central Sheffield.
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Bartholomews Cobble

Bartholomews Cobble is 4.2 mi (6.8 km) from central Sheffield, why not stop by during your stay. Want to stretch your legs some more? Head to Eddy Field and Lawrence Field, both nearby.
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Learn more about Sheffield

Sheffield is well-known for its attractions such as Housatonic River and Thom Reed UFO Monument Park.

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FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Check out reviews of Sheffield hotels guests love

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Our room was spotless and cozy. I was very pleased to be able to control the temperature as I like to sleep in a cool room. The shower and sink products are lovely -- especially the moisturizer for cold weather skin. I cannot speak highly enough about the restaurant -- beautiful decor, delicious cocktails, amazing food, everything we ordered was great!"
Joanna 4-night trip
Posted 4 days ago
Berkshires Untold

Frequently asked questions

What accommodations do travelers recommend in Sheffield?
Wilder House Berkshires is an accommodation that is popular with guests.
Can I book a refundable accommodation in Sheffield?
If you want the flexibility to change your travel plans to Sheffield, most accommodations offer refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Sheffield if I want a vacation rental instead of a traditional hotel?
If you want to find a good alternative to a hotel, browse our selection of 25 vacation homes.
What will the weather in Sheffield be like during my vacation?
The warmest months in Sheffield are usually July and August with an average temp of 66°F. January and February are the chilliest months when the average temp is 28°F. The rainiest months are July and August.
Why should I book my Sheffield accommodation with Hotels.com?
There are plenty of reasons to book your Sheffield travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.