Hotels in Sheffield

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Jul 10 - Jul 12
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Jul 17 - Jul 19

Where to stay in Sheffield?

Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (56 reviews)
Escape to the Berkshires in this inviting Sheffield accommodation with complimentary WiFi and parking. Start your day with cooked-to-order weekend breakfast before exploring nearby Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary.
The price is $174
$194 total
includes taxes & fees
Jul 7 - Jul 8
Wilder House Berkshires
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
Discover this Lenox retreat with stunning mountain views, year-round swimming options, and fireplaces in select rooms. Just minutes from Bousquet Ski Area and local attractions, enjoy free breakfast and helpful staff after a day exploring.
The price is $127
$142 total
includes taxes & fees
Jul 6 - Jul 7
The Yankee Inn
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (481 reviews)
The price is $75
$84 total
includes taxes & fees
Jul 6 - Jul 7
Berkshire Travel Lodge
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
Escape to the heart of the Berkshires in this well-maintained motel close to Tanglewood Music Center. Free WiFi and parking make exploring local attractions like Hoffman's Pottery and Charles H. Baldwin & Sons effortless. Clean rooms and daily housekeeping ensure a comfortable stay.
The price is $82
$90 total
includes taxes & fees
Jul 7 - Jul 8
Pleasant Valley Motel West Stockbridge
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
Experience tranquility at this West Stockbridge B&B where hiking, biking, and kayaking adventures await. Enjoy free breakfast, complimentary parking, and daily housekeeping while exploring Ebenezer II Gifts and nearby cultural attractions.
The price is $179
$196 total
includes taxes & fees
Jul 6 - Jul 7
Shaker Mill Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (576 reviews)
Experience comfort and convenience at this motel in Great Barrington, where free WiFi and parking await. Explore nearby Monument Mountain Reservation for hiking, then return to spotless rooms with daily housekeeping and notably helpful staff.
The price is $112
$125 total
includes taxes & fees
Jul 6 - Jul 7
The Little Lion
Free WiFi, bed sheets

Hitching Post Country Motel

Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.8 out of 10, (94 reviews)
This countryside motel offers free WiFi and parking with 24-hour front desk assistance. Located near Housatonic Meadows State Park and Clarke Outdoors, it's perfect for outdoor enthusiasts looking to explore hiking trails and snowboarding venues.
The price is $130
$150 total
includes taxes & fees
Jul 6 - Jul 7
Hitching Post Country Motel
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (190 reviews)
Unwind in this peaceful country retreat with a seasonal outdoor pool and complimentary gourmet breakfast. Located near Haystack Mountain State Park, the inn offers free WiFi and parking while helpful staff ensure a memorable stay in Norfolk's quiet surroundings.
The price is $156
$179 total
includes taxes & fees
Jul 6 - Jul 7
Blackberry River Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,002 reviews)
This peaceful Lee hotel offers free daily continental breakfast near local restaurants and shopping. Just minutes from Lee Library and Animagic Museum, guests praise the helpful staff. Enjoy convenient access to cultural attractions during your Berkshires stay.
The price is $135
$151 total
includes taxes & fees
Jul 27 - Jul 28
Quality Inn Lee - Lenox South
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (879 reviews)
Dive into Berkshires charm at this centrally located Lenox motel, where you'll enjoy the refreshing outdoor pool and free parking. Near Guido's Marketplace and Bousquet Ski Area, with clean rooms and exceptionally helpful staff to enhance your stay.
The price is $99
$111 total
includes taxes & fees
Jul 6 - Jul 7
Howard Johnson by Wyndham Lenox
BBQ/picnic area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very Good, (11 reviews)
The price is $167
$187 total
includes taxes & fees
Jul 6 - Jul 7
Hideaway Inn Lenox
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (91 reviews)
Escape to this mountain lodge near Catamount Ski Area, featuring a seasonal outdoor pool and relaxing sauna. After alpine adventures, savor complimentary breakfast before unwinding at the bar. Free WiFi and parking round out this Copake Falls retreat.
The price is $169
$189 total
includes taxes & fees
Jul 6 - Jul 7
Little Cat Lodge
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (876 reviews)
The price is $124
$138 total
includes taxes & fees
Jul 6 - Jul 7
Monument Mountain Motel
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (1,005 reviews)
Nestled in Lenox, this lodge offers easy access to Kennedy Park and Pleasant Valley Wilderness Sanctuary. The Club Room serves American cuisine, while the terrace provides a perfect spot to unwind after exploring local attractions.
The price is $149
$166 total
includes taxes & fees
Jul 7 - Jul 8
Berkshires Untold
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (429 reviews)
Wake up to a complimentary full breakfast at this cozy East Canaan B&B. Located near Land of Nod Vineyard and Winery, the inn offers free parking and daily housekeeping. Guests consistently praise the helpful staff for making stays memorable.
The price is $105
$121 total
includes taxes & fees
Jul 12 - Jul 13
Locust Tree Bed and Breakfast LLC
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,015 reviews)
The price is $135
$173 total
includes taxes & fees
Aug 4 - Aug 5
Berkshire Mountain Lodge
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,004 reviews)
The price is $167
$231 total
includes taxes & fees
Jul 6 - Jul 7
The Red Lion Inn
Exterior

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires
3.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
Wake up to free breakfast at this cozy Berkshires inn where a garden terrace offers peaceful moments. The coffee shop/cafe and bar provide refreshments after exploring nearby attractions like The Bookstore and Lenox Library.
The price is $131
$151 total
includes taxes & fees
Jul 6 - Jul 7
The Cornell Inn, Lenox & The Berkshires
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,007 reviews)
This peaceful hotel offers complimentary breakfast, WiFi, and parking, with Mahaiwe Performing Arts Center just moments away. Fitness enthusiasts will appreciate the on-site gym and outdoor activities, while the helpful staff ensures a comfortable stay.
The price is $101
$113 total
includes taxes & fees
Aug 2 - Aug 3
Quality Inn Great Barrington
Egyptian cotton sheets, premium bedding, memory foam beds, desk

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (141 reviews)
Tucked in Hillsdale, this cozy motel offers premium bedding for après-ski relaxation, plus free WiFi and parking. Adventure awaits at nearby Catamount Aerial Adventure Park, with cross-country and downhill skiing just moments away.
The price is $140
$156 total
includes taxes & fees
Jul 6 - Jul 7
The Brooks 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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When is the best time to visit Sheffield?

Our prices for hotels in Sheffield are cheapest in April
Price trends for hotels in Sheffield
Pricing is based on two traveler single night rates
View properties in July
Currently viewing crowd sizes and weather for July.
Typical weather for Sheffield
July
High 27°C / low 16°C. Sunny most days.
View properties in July
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July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 15 degrees Celsius, average low temperature 6 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 8 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 2 degrees Celsius, average low temperature -5 degrees Celsius. Snow likely.
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January, no crowd data, average high temperature -1 degrees Celsius, average low temperature -9 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 0 degrees Celsius, average low temperature -8 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 5 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
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April, no crowd data, average high temperature 12 degrees Celsius, average low temperature 2 degrees Celsius. Cloudy most days.
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May, no crowd data, average high temperature 19 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 23 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Sheffield

Bartholomew's Cobble

10.0/10 (1 review)
Bartholomew's Cobble is 3.8 mi (6.1 km) from central Sheffield, why not stop by during your stay.
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Learn more about Sheffield

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

See all hotels in Sheffield
A covered wooden structure with a sloped roof, surrounded by greenery and trees.

Check out reviews of Sheffield hotels guests love

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"The condo unit was a pleasant surprise for a weekend away. It was clean and well maintained. We enjoyed one if the onsite pools. Unfortunately, when we returned in the evening to swim inside, a group of 4 people ( yes, only 4) had rudely taken over the space and were so loud, that we left. We would definitely return for another stay."
Lori 2-night trip
Posted 4 hours ago
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Frequently asked questions

What accommodations do travelers recommend in Sheffield?
Guests like Wilder House Berkshires, Quality Inn Great Barrington and Holiday Inn Express Hotel & Suites Great Barrington by IHG.
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 21 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.