Hotels in Sheffield

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This weekend
May 22 - May 24
Next weekend
May 29 - May 31

Where to stay in Sheffield?

Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (49 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 $193
$215 total
includes taxes & fees
May 27 - May 28
Wilder House Berkshires
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,001 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 $85
$94 total
includes taxes & fees
May 25 - May 26
Quality Inn Great Barrington
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
The price is $247
$276 total
includes taxes & fees
May 25 - May 26
The Berkshire Mountain Inn
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (45 reviews)
This cozy motel offers complimentary WiFi and parking, making outdoor adventures hassle-free. Explore the nearby Housatonic River and River Walk, or try kayaking and mountain biking. Garden views provide a serene backdrop for your Berkshires escape.
The price is $149
$167 total
includes taxes & fees
Jun 21 - Jun 22
East Rock Inn
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, (856 reviews)
The price is $76
$85 total
includes taxes & fees
May 25 - May 26
Monument Mountain Motel
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 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
May 24 - May 25
Locust Tree Bed and Breakfast LLC
Exterior

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (780 reviews)
This tranquil hotel offers sound-insulated accommodations near Housatonic River and River Walk. Guests love the helpful staff, clean rooms, indoor pool, and 24-hour fitness center. Enjoy free breakfast, WiFi, and parking while exploring Great Barrington's nearby restaurants.
The price is $167
$186 total
includes taxes & fees
May 26 - May 27
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (766 reviews)
Refresh in the indoor pool at this welcoming Great Barrington hotel. The fitness center adds value to each stay, while free breakfast fuels adventures to nearby Lake Mansfield Park and Housatonic River. Guests rave about the clean rooms and helpful staff.
The price is $115
$128 total
includes taxes & fees
May 25 - May 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Front of property

Gedney Farm

Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (137 reviews)
Unwind at this charming Great Barrington retreat featuring complimentary breakfast, WiFi, and parking. The hotel offers a restaurant, welcoming bar, and tranquil outdoor spaces near Questing and New Marlborough Town Library.
The price is $175
$192 total
includes taxes & fees
May 25 - May 26
Gedney Farm
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (78 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
May 25 - May 26
Little Cat Lodge
Breakfast, lunch, dinner and brunch served

The Old Inn On The Green

The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (91 reviews)
Experience culinary delights at The Old Inn Fine Dining, featuring American cuisine for breakfast, lunch, and dinner. Cool off in the seasonal pool, then sip drinks at the bar. Nearby attractions Questing and New Marlborough Town Library await your exploration.
The price is $330
$398 total
includes taxes & fees
May 25 - May 26
The Old Inn On The Green
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (580 reviews)
The price is $75
$84 total
includes taxes & fees
May 25 - May 26
Travelodge by Wyndham Great Barrington Berkshires
Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.8 out of 10, Exceptional, (26 reviews)
Scenic Berkshires escape featuring an outdoor pool and rejuvenating sauna. Enjoy local flavors at The Cliff House restaurant after exploring nearby Catamount attractions. Free WiFi and parking make this wooded sanctuary even more appealing.
The price is $311
$380 total
includes taxes & fees
May 25 - May 26
Prospect Berkshires
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 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 $95
$106 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (101 reviews)
This charming business-friendly B&B offers free full breakfast, WiFi, and parking in scenic Housatonic. Explore nearby Monument Mountain and its reservation, with Pittsfield Municipal Airport just a 28-minute drive away.
The price is $275
$307 total
includes taxes & fees
Jun 1 - Jun 2
Granville House
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (181 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
May 24 - May 25
Blackberry River Inn
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, (136 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 $130
$145 total
includes taxes & fees
May 25 - May 26
The Brooks Motel
Exterior

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (222 reviews)
Experience tranquil moments at this countryside retreat near Undermountain Golf Course and Copake Town Park. North Star restaurant serves American cuisine for dinner, while free WiFi and parking add convenience. Guests consistently praise the attentive staff who enhance every stay.
The price is $170
$190 total
includes taxes & fees
May 25 - May 26
the Alander
Interior

Charming 6 Bdrm Countryside Stay

Charming 6 Bdrm Countryside Stay
3.0 star property
Great Barrington
The price is $748
$1,336 total
includes taxes & fees
Jun 1 - Jun 2
Charming 6 Bdrm Countryside Stay
John Harney Suite | Minibar, desk, iron/ironing board, free WiFi

The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (151 reviews)
A charming stay in Salisbury at this historic hotel with a welcoming bar and café. Unwind in the peaceful garden or relax on the terrace after exploring nearby Mount Frissell and Hanging Rock Park. Free breakfast, WiFi, and parking enhance your visit.
The price is $343
$395 total
includes taxes & fees
May 25 - May 26
The White Hart
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 May
Price trends for hotels in Sheffield
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for Sheffield
May
High 19°C / low 8°C. Sunny most days.
View properties in May
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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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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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Monthly weather averages (˚C)

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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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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"The front porch. The dining rooms. The staff. Everything was perfect from the time we entered until the time we departed."
Nicholas 1-night trip
Posted 3 hours ago
The Red Lion Inn

Frequently asked questions

What accommodations do travelers recommend in Sheffield?
Guests like Wilder House Berkshires, Quality Inn Great Barrington and The Little Lion.
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.