Hotels in Sheffield

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Tonight
Apr 11 - Apr 12
Tomorrow
Apr 12 - Apr 13
Next weekend
Apr 17 - Apr 19
In two weeks
Apr 24 - Apr 26

Where to stay in Sheffield?

Interior detail
Wilder House Berkshires
Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (44 reviews)
  • cleanliness
    Stay at a charming Sheffield B&B with a convenient weekend breakfast service.
The price is $161
$180 total
includes taxes & fees
Apr 14 - Apr 15
Wilder House Berkshires
Front of property
Becket Motel
Becket Motel
2.5 star property
Becket
6.8 out of 10, (60 reviews)
  • cleanliness
    Contemporary Berkshires retreat with natural surroundings and nearby trails.
The price is $105
$151 total
includes taxes & fees
Apr 13 - Apr 14
Becket Motel
Library
Blackberry River Inn
Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (173 reviews)
  • cleanliness
    Relax at this historic B&B in scenic Norfolk, surrounded by nature's tranquility.
The price is $156
$179 total
includes taxes & fees
Apr 13 - Apr 14
Blackberry River Inn
Front of property
Gedney Farm
Gedney Farm
3.5 star property
Great Barrington
9.4 out of 10, Exceptional, (136 reviews)
  • cleanliness
    Rustic farm hotel in the Berkshires with on-site dining and peaceful gardens.
The price is $206
$226 total
includes taxes & fees
Apr 13 - Apr 14
Gedney Farm
Breakfast, lunch, dinner served; American cuisine
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)
  • cleanliness
    Seasonal escape in historic Great Barrington with outdoor pool and fine dining.
The price is $305
$368 total
includes taxes & fees
Apr 13 - Apr 14
The Old Inn On The Green
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, (416 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
Apr 13 - Apr 14
Locust Tree Bed and Breakfast LLC
Free WiFi, bed sheets
Hitching Post Country Motel
Hitching Post Country Motel
2.5 star property
Cornwall Bridge
6.6 out of 10, (83 reviews)
  • cleanliness
    Wake up to New England charm in this quaint motel set near hiking trails and parks.
The price is $130
$150 total
includes taxes & fees
Apr 13 - Apr 14
Hitching Post Country Motel
Lobby
Quality Inn Lee - Lenox South
Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,000 reviews)
  • cleanliness
    A cozy retreat 15 minutes from Tanglewood Music Center with complimentary WiFi.
The price is $93
$104 total
includes taxes & fees
Apr 26 - Apr 27
Quality Inn Lee - Lenox South
Seasonal outdoor pool
Sunset Inn
Sunset Inn
2.0 star property
Lee
7.6 out of 10, Good, (412 reviews)
  • cleanliness
    Countryside lodging with a seasonal pool, steps away from Tanglewood Music Center.
The price is $100
$112 total
includes taxes & fees
Apr 13 - Apr 14
Sunset Inn
Front of property
Chambery Inn
Chambery Inn
3.0 star property
Lee
9.6 out of 10, Exceptional, (376 reviews)
  • cleanliness
    Peaceful countryside retreat with spa treatments just minutes from Tanglewood Music Center.
The price is $190
$212 total
includes taxes & fees
Apr 13 - Apr 14
Chambery Inn
In-room dining
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (661 reviews)
  • cleanliness
    Cozy retreat near Lee Premium Outlets with mini golf and continental breakfast.
The price is $67
$75 total
includes taxes & fees
Apr 26 - Apr 27
Econo Lodge Lee - Great Barrington
Free daily continental breakfast
Cornwall Inn and Lodge
Cornwall Inn and Lodge
3.0 star property
Cornwall Bridge
9.2 out of 10, Wonderful, (158 reviews)
  • cleanliness
    Cozy Connecticut inn with complimentary breakfast and a seasonal pool to enjoy.
The price is $212
$243 total
includes taxes & fees
Apr 13 - Apr 14
Cornwall Inn and Lodge
Front of property - evening/night
Devonfield Inn B&B
Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (137 reviews)
  • cleanliness
    Step back from the crowds with a relaxing Berkshires escape next to scenic fairways.
The price is $299
$334 total
includes taxes & fees
Apr 14 - Apr 15
Devonfield Inn B&B
Lake
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Tranquil lakefront escape with stunning sunset views and a 24-hour fitness center.
The price is $100
$112 total
includes taxes & fees
Apr 19 - Apr 20
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Property amenity
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, (864 reviews)
  • cleanliness
    Berkshire getaway offers indoor and outdoor pools with mountain scenery and cafe.
The price is $113
$145 total
includes taxes & fees
Apr 29 - Apr 30
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Front of property
The Inn at Stockbridge
The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
  • cleanliness
    Unwind in the Berkshires with massages and outdoor swimming in charming Lee.
The price is $251
$294 total
includes taxes & fees
Apr 24 - Apr 25
The Inn at Stockbridge
Indoor pool
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (88 reviews)
  • cleanliness
    Lakeside getaway in Berkshires with indoor pool and Tanglewood Music Center nearby.
The price is $118
$132 total
includes taxes & fees
Apr 16 - Apr 17
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Breakfast, lunch and dinner served
Hilton Garden Inn Lenox Pittsfield
Hilton Garden Inn Lenox Pittsfield
3.0 star property
Pittsfield
9.2 out of 10, Wonderful, (673 reviews)
  • cleanliness
    Modern hotel near Herman Melville's Arrowhead with indoor pool and Asian fusion dining.
The price is $137
$153 total
includes taxes & fees
Apr 16 - Apr 17
Hilton Garden Inn Lenox Pittsfield
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, (846 reviews)
  • cleanliness
    Experience Lenox from a central motel with a pool and friendly staff at your service.
The price is $79
$88 total
includes taxes & fees
Apr 13 - Apr 14
Howard Johnson by Wyndham Lenox
Lobby
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (901 reviews)
The price is $88
$120 total
includes taxes & fees
May 11 - May 12
Berkshire Mountain Lodge
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.
View all properties

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.
See properties

Drury Preserve

Drury Preserve is 2.5 mi (3.9 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

Quality Inn Great Barrington

Quality Inn Great Barrington

10/10 Excellent
"would come again to stay if around the area compared to Red Lion. "
Juliet 1-night trip
Posted 2 hours ago
Quality Inn Great Barrington

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 23 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.