Hotels in Sheffield

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Wilder House Berkshires
Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (42 reviews)
  • cleanliness
    Stay at a charming Sheffield B&B with a convenient weekend breakfast service.
The price is $182
$203 total
includes taxes & fees
Jan 19 - Jan 20
Wilder House Berkshires
Quality Inn Great Barrington
Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    Explore the serene setting of Great Barrington with hiking trails and ski slopes nearby.
The price is $70
$79 total
includes taxes & fees
Feb 5 - Feb 6
Quality Inn Great Barrington
Monument Mountain Motel
Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (816 reviews)
The price is $67
$74 total
includes taxes & fees
Jan 19 - Jan 20
Monument Mountain Motel
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
Great Barrington
9.4 out of 10, Exceptional, (761 reviews)
  • cleanliness
    Rest peacefully near Housatonic River with soundproof rooms and complimentary perks.
The price is $135
$151 total
includes taxes & fees
Jan 29 - Jan 30
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Locust Tree Bed and Breakfast LLC
Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413 reviews)
  • cleanliness
    Experience the charm of East Canaan at this bed and breakfast with countryside views.
The price is $105
$121 total
includes taxes & fees
Jan 16 - Jan 17
Locust Tree Bed and Breakfast LLC
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, (719 reviews)
  • cleanliness
    Located in Great Barrington with free breakfast, WiFi, and parking for easy explorations.
The price is $107
$120 total
includes taxes & fees
Jan 22 - Jan 23
Holiday Inn Express Hotel & Suites Great Barrington by IHG
East Rock Inn
East Rock Inn
2.0 star property
Great Barrington
9.6 out of 10, Exceptional, (37 reviews)
  • cleanliness
    Set in Great Barrington with hiking trails and river access just moments away.
The price is $139
$155 total
includes taxes & fees
Jan 19 - Jan 20
East Rock Inn
The Old Inn On The Green
The Old Inn On The Green
4.0 star property
Great Barrington
9.2 out of 10, Wonderful, (90 reviews)
  • cleanliness
    Seasonal escape in historic Great Barrington with outdoor pool and fine dining.
The price is $305
$368 total
includes taxes & fees
Jan 18 - Jan 19
The Old Inn On The Green
Gedney Farm
Gedney Farm
3.5 star property
Great Barrington
9.2 out of 10, Wonderful, (134 reviews)
  • cleanliness
    Rustic farm hotel in the Berkshires with on-site dining and peaceful gardens.
The price is $206
$226 total
includes taxes & fees
Jan 18 - Jan 19
Gedney Farm
Prospect Berkshires
Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18 reviews)
  • cleanliness
    Relax amid tranquil woods at a Great Barrington retreat with spa services and dining.
The price is $186
$241 total
includes taxes & fees
Jan 25 - Jan 26
Prospect Berkshires
Little Cat Lodge
Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (66 reviews)
  • cleanliness
    Rustic alpine charm by the Catskills with a Nordic-inspired restaurant and sauna.
The price is $189
$212 total
includes taxes & fees
Jan 19 - Jan 20
Little Cat Lodge
Granville House
Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (92 reviews)
  • cleanliness
    Relax in a cozy Housatonic B&B with complimentary breakfast and nearby attractions.
The price is $174
$194 total
includes taxes & fees
Jan 16 - Jan 17
Granville House
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (566 reviews)
The price is $75
$84 total
includes taxes & fees
Jan 19 - Jan 20
Travelodge by Wyndham Great Barrington Berkshires
The Little Lion
The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (548 reviews)
  • cleanliness
    Restful home base near Monument Mountain with easy access to outdoor adventures.
The price is $110
$123 total
includes taxes & fees
Jan 18 - Jan 19
The Little Lion
Blackberry River Inn
Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (166 reviews)
  • cleanliness
    Relax at this historic B&B in scenic Norfolk, surrounded by nature's tranquility.
The price is $164
$189 total
includes taxes & fees
Jan 19 - Jan 20
Blackberry River Inn
The Brooks Motel
The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (124 reviews)
  • cleanliness
    Ski lodge convenience near winter sports with comfy rooms and free amenities.
The price is $129
$144 total
includes taxes & fees
Jan 19 - Jan 20
The Brooks Motel
The White Hart
The White Hart
4.0 star property
Salisbury
9.6 out of 10, Exceptional, (145 reviews)
  • cleanliness
    Restored 17th-century inn with garden views, near Mount Frissell.
The price is $245
$281 total
includes taxes & fees
Jan 19 - Jan 20
The White Hart
the Alander
the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (197 reviews)
  • cleanliness
    Serene Copake lodge surrounded by natural beauty with American dining onsite.
The price is $140
$157 total
includes taxes & fees
Jan 19 - Jan 20
the Alander
9 Academy
9 Academy
4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10 reviews)
  • cleanliness
    Countryside retreat with snowboarding nearby and garden views to complement stay.
The price is $478
$550 total
includes taxes & fees
Jan 18 - Jan 19
9 Academy
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
3.5 star property
South Lee
9.0 out of 10, Wonderful, (818 reviews)
  • cleanliness
    Berkshire getaway offers indoor and outdoor pools with mountain scenery and cafe.
The price is $113
$145 total
includes taxes & fees
Jan 19 - Jan 20
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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.

Top landmarks in Sheffield

Learn more about Sheffield

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

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

Check out reviews of Sheffield hotels guests love

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 24 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.