Find Luxury Hotels in Sheffield, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Sheffield Luxury Hotels

Our top choices for Sheffield luxury hotels

Exterior

Troutbeck

Troutbeck
5.0 star property
Amenia
The price is ￥79,067
￥95,833 total
includes taxes & fees
Mar 16 - Mar 17
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 ￥31,221
￥35,904 total
includes taxes & fees
Mar 18 - Mar 19
The White Hart
Porch

Lakehouse Inn

Lakehouse Inn
4.0 star property
Lee
9.6 out of 10, Exceptional, (294 reviews)
"Friendly staff, great location, beautiful views, cozy room."
United States
Elizabeth
The price is ￥22,081
￥25,897 total
includes taxes & fees
Mar 20 - Mar 21
Lakehouse Inn
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 ￥84,857
￥97,585 total
includes taxes & fees
Mar 23 - Mar 24
9 Academy
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 ￥67,861
￥75,800 total
includes taxes & fees
Mar 26 - Mar 27
33 Main
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)
"Beautiful Inn and outstanding chef"
United States
Catherine
The price is ￥48,718
￥58,789 total
includes taxes & fees
Mar 16 - Mar 17
The Old Inn On The Green
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
The price is ￥47,296
￥52,831 total
includes taxes & fees
Mar 18 - Mar 19
Devonfield Inn B&B
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 ￥49,432
￥59,800 total
includes taxes & fees
Mar 28 - Mar 29
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 ￥38,144
￥44,738 total
includes taxes & fees
Mar 27 - Mar 28
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
The price is ￥36,722
￥41,017 total
includes taxes & fees
Mar 22 - Mar 23
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
"Easy check-in; accommodating staff; clean room. Convenient but also quiet location."
Nathaniel 3-night trip
Posted 3 days 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 Three Mile Pond Wildlife Management Area and Ashley House.