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Check availability on Sheffield Luxury Hotels

Tonight
Mar 6 - Mar 7
Tomorrow
Mar 7 - Mar 8
This weekend
Mar 6 - Mar 8
Next weekend
Mar 13 - Mar 15

Our top choices for Sheffield luxury hotels

Terrace/patio

Troutbeck

Troutbeck
5.0 star property
Amenia
The price is ￥86,647
￥104,321 total
includes taxes & fees
Mar 12 - Mar 13
Troutbeck
Exterior

The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (147 reviews)
"Such a cozy, authentic New England hotel, with all its charm. "
United States
Maulik
The price is ￥37,822
￥43,495 total
includes taxes & fees
Mar 8 - Mar 9
The White Hart
The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

9 Academy

9 Academy
4.0 star property
Salisbury
9.2 out of 10, Wonderful, (11 reviews)
"Nice room. "
South Korea
JeongHoon
The price is ￥75,324
￥86,623 total
includes taxes & fees
Mar 23 - Mar 24
9 Academy
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, (90 reviews)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is ￥47,873
￥57,769 total
includes taxes & fees
Apr 6 - Apr 7
The Old Inn On The Green
Exterior

33 Main

33 Main
4.0 star property
Lenox
10.0 out of 10, Exceptional, (74 reviews)
"Beautiful place. Wonderful owner and staff. Our stay there was a total delight."
United States
James
The price is ￥70,822
￥79,108 total
includes taxes & fees
Mar 8 - Mar 9
33 Main
Room #10 Queen's Cottage | Living room | Flat-screen TV

Devonfield Inn B&B

Devonfield Inn B&B
4.0 star property
Lee
10.0 out of 10, Exceptional, (136 reviews)
"The inn has an excellent location and amenities."
United States
Christopher
Devonfield Inn B&B
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (294 reviews)
"A charming inn in the center of the Berkshires."
United States
Danny
The price is ￥21,326
￥25,012 total
includes taxes & fees
Mar 20 - Mar 21
Lakehouse Inn
Suite, Private Bathroom (RedBird Suite) | View from room

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is ￥48,754
￥58,979 total
includes taxes & fees
Mar 20 - Mar 21
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is ￥37,621
￥44,125 total
includes taxes & fees
Mar 29 - Mar 30
The Inn at Stockbridge
Exterior detail

Hampton Terrace Inn

Hampton Terrace Inn
4.0 star property
Lenox
9.0 out of 10, Wonderful, (44 reviews)
"Comfortable bed. Quiet location. Excellent breakfast. Friendly host."
United States
Kathleen
Hampton Terrace Inn
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 Sheffield Hotel Reviews

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Absolutely friendly staff. Recognized me from previous stays. "
Susan 2-night trip
Posted 17 hours ago
The Yankee, Trademark Collection by Wyndham

Frequently asked questions

Are you looking for a luxury hotel for your Sheffield vacation?
Use Expedia to arrange your flight to Pittsfield, MA (PSF-Pittsfield Municipal) airport or Hudson, NY (HCC-Columbia County) airport, and then select from a variety of places to stay that will deliver the luxury you want. Amenities are important when you plan a trip, so we make it easy to find what you need to make your stay relaxing and comfortable. If you want an upscale hotel with a spa, an indoor pool, or luxury bedding, Expedia can help you find the best luxury hotel experience that Sheffield offers. Sheffield has some interesting things to see and do including Housatonic River and Lime Kiln Farm Wildlife Sanctuary, so you might want to take in the local sights during your visit.
When can I expect good weather in Sheffield?
Planning for the weather is a good way to make your trip to Sheffield relaxing and enjoyable, especially when you're splurging. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 28°F. The snowiest months in Sheffield are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's there to see and do in Sheffield?
Enjoy all that Sheffield has to offer and visit Housatonic River, Lime Kiln Farm Wildlife Sanctuary, and Magnolia Bluffs Casino. If you have extra time while you're in the area, you might want to see Drury Preserve and Ashley House.