Hotels in Sheffield

Free cancellation options if plans change

Unlock travel rewards with One Key

Save more with Member Prices

Check prices for these dates

Tonight
Nov 23 - Nov 24
Tomorrow
Nov 24 - Nov 25
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Where to stay in Sheffield?

Wilder House Berkshires Room 3 | 1 bedroom, premium bedding, individually decorated
Wilder House Berkshires
Wilder House Berkshires
2.0 star property
9.8 out of 10, Exceptional, (38)
$144 nightly
The price is $161
Nov 24 - Nov 25
Total with taxes and fees
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.
See more propertiesforward arrow

The Black Friday Sale is now on

Get up to 50% off select hotels in our biggest sale of the year
Shop Black Friday deals

When is the best time to visit Sheffield?

Our prices for hotels in Sheffield are cheapest in October
Price trends for hotels in Sheffield
Pricing is based on two traveler single night rates
View properties in November
Currently viewing crowd sizes and weather for November.
Typical weather for Sheffield
November
Moderate crowds
High 46°F / low 31°F. Partly sunny.
View properties in November
46°
weather_partly_sunny
November, Moderate crowds, average high temperature 46 degrees Fahrenheit, average low temperature 31 degrees Fahrenheit. Partly sunny.
31°
36°
ac_unit
December, Moderate crowds, average high temperature 36 degrees Fahrenheit, average low temperature 24 degrees Fahrenheit. Snow likely.
24°
30°
ac_unit
January, Low crowds, average high temperature 30 degrees Fahrenheit, average low temperature 16 degrees Fahrenheit. Snow likely.
16°
33°
ac_unit
February, Low crowds, average high temperature 33 degrees Fahrenheit, average low temperature 17 degrees Fahrenheit. Snow likely.
17°
41°
ac_unit
March, Low crowds, average high temperature 41 degrees Fahrenheit, average low temperature 25 degrees Fahrenheit. Snow likely.
25°
54°
weather_cloudy
April, Low crowds, average high temperature 54 degrees Fahrenheit, average low temperature 35 degrees Fahrenheit. Cloudy most days.
35°
66°
weather_sun
May, Moderate crowds, average high temperature 66 degrees Fahrenheit, average low temperature 46 degrees Fahrenheit. Sunny most days.
46°
73°
weather_sun
June, High crowds, average high temperature 73 degrees Fahrenheit, average low temperature 54 degrees Fahrenheit. Sunny most days.
54°
80°
weather_sun
July, High crowds, average high temperature 80 degrees Fahrenheit, average low temperature 60 degrees Fahrenheit. Sunny most days.
60°
78°
weather_sun
August, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 59 degrees Fahrenheit. Sunny most days.
59°
71°
weather_sun
September, Moderate crowds, average high temperature 71 degrees Fahrenheit, average low temperature 52 degrees Fahrenheit. Sunny most days.
52°
58°
weather_sun
October, High crowds, average high temperature 58 degrees Fahrenheit, average low temperature 42 degrees Fahrenheit. Sunny most days.
42°
Monthly weather averages (˚F)

Top landmarks in Sheffield

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 Umpachene Falls Park and Eddy Field, both nearby.
See properties

Bartholomew's Cobble

Bartholomew's Cobble is 3.8 mi (6.1 km) from central Sheffield, why not stop by during your stay.
See properties

Learn more about Sheffield

Sheffield is well-known for its attractions such as Housatonic River and Magnolia Bluffs Casino.

See all hotels in Sheffield
FTYTP1 The Upper Sheffield Covered Bridge, Sheffield, Massachusetts, USA

Check out reviews of Sheffield hotels guests love

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Like having a fully equipped small apartment "
Francis 7-night trip
Posted 4 days ago
Berkshire Mountain Lodge

Frequently asked questions

How much does a hotel room cost in Sheffield?
You can choose a great hotel in Sheffield with properties to suit all budgets and needs. To find an affordable hotel in Sheffield that meets all of your requirements, just apply filters on Hotels.com, and sort hotels by "Price: low to high". If you're a member, don't forget to sign in to your account to unlock more savings.
How can I find deals and earn rewards at Sheffield hotels?
Members can save up to 20% on select hotels in Sheffield. Plus, Silver, Gold and Platinum members earn extra rewards on VIP Access bookings, making each stay even more rewarding.

Can I book Sheffield hotels with free cancellation?
In order to book a refundable Sheffield hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some popular hotels in central Sheffield?
If you're looking for hotels in central Sheffield, check out The Egremont Village Inn. Travelers love The Egremont Village Inn for its location, as well as the restaurant, bar/lounge and coffee shop/cafe this inn offers.
Are all taxes and fees included in the Sheffield hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.
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.

Find out more about Sheffield

Sheffield: Where Urban Charm Meets Nature's Embrace

Nestled in the picturesque Berkshire Hills, Sheffield, Massachusetts, is a hidden gem perfect for nature lovers and history buffs alike. This quaint town boasts stunning landscapes, including rolling hills and lush farmlands, ideal for hiking and outdoor adventures. Explore the charming village center, where historic architecture meets local artisan shops and farm-to-table eateries. Don’t miss the nearby Bartholomew’s Cobble, a breathtaking nature preserve with diverse trails and wildlife. Sheffield's serene ambiance and rich cultural heritage make it an enchanting getaway for those seeking tranquility and inspiration in the heart of New England. For great hotel rates in Sheffield, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Top locations to stay in Sheffield

When visiting Sheffield, Massachusetts, great places to stay include Great Barrington, Lakeville, and Salisbury. Great Barrington offers vibrant nightlife and cultural attractions like the Norman Rockwell Museum. Lakeville is perfect for museum enthusiasts and outdoor adventures. Salisbury boasts stunning natural parks and scenic mountains. For first-time visitors, Great Barrington is the most appealing choice with its diverse activities and attractions.

  1. Great BarringtonOpens in a new window: Great Barrington is a charming town bursting with artistic flair and natural beauty. It's an ideal spot for travelers looking to explore local culture and stunning landscapes. You can immerse yourself in art at the Norman Rockwell Museum or unwind at The Mount, the historic home of writer Edith Wharton. For those who love the outdoors, the Housatonic River Walk offers a peaceful escape, while nearby Ski Butternut and Catamount Ski Area offer winter sports for the adventurous. Shopping enthusiasts will appreciate the unique offerings at Charles H. Baldwin & Sons and the Lee Premium Outlets, perfect for picking up local goods and popular brands alike.
  2. LakevilleOpens in a new window: Nestled in the picturesque Litchfield Hills, Lakeville is perfect for travelers seeking a blend of nature and culture. The area is rich in outdoor beauty, boasting scenic spots like Taconic State Park and Bash Bish Falls State Park, ideal for hiking and photography. Lakeville also houses various cultural attractions, including local museums that showcase regional history. For a fun outing, you can explore the Harlem Valley Rail Trail, perfect for biking and walking, or check out the nearby Lime Rock Park for motorsport events. The local shopping options, such as Ames Plaza Shopping Center, provide a quaint shopping experience.
  3. SalisburyOpens in a new window: Salisbury is a serene town that offers a perfect getaway for nature lovers and those looking to relax. The majestic views from Taconic State Park and Bash Bish Falls State Park are a must-see, providing stunning backdrops for outdoor activities. If you're interested in local arts, the town hosts cultural attractions that reflect its rich heritage. Adventurers can enjoy the Harlem Valley Rail Trail, which is great for hiking or cycling. For a unique shopping experience, visit the Bodhi Tree Gallery, where you can find handcrafted items that capture the essence of the area. Salisbury's tranquil atmosphere makes it a delightful place to unwind.

Keep exploring