Sheffield, MA
Travel Guide
Visit Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
$195 nightly
The price is $218 total per night from Aug 9 to Aug 10
$218 total
Aug 9 - Aug 10
Total with taxes and fees
Stay at this B&B in Sheffield. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife ...
The Yankee Inn
461 Pittsfield Rd Lenox MA
$158 nightly
The price is $176 total per night from Aug 5 to Aug 6
$176 total
Aug 5 - Aug 6
Total with taxes and fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9.2/10 Wonderful! (1,004 reviews)
"Nice quiet hotel and great room. Good pool and hot tub. Convenient location at reasonable price. Staff were helpful too."
Reviewed on Aug 4, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$138 nightly
The price is $155 total per night from Aug 30 to Aug 31
$155 total
Aug 30 - Aug 31
Total with taxes and fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,041 reviews)
"It would have been the perfect place if the concert at Tanglewood had not been postponed. The checkin went well, the rooms were spacious and clean, and the location was good. Plenty of parking and there are plenty of restaurants nearby for lunch or dinner. Overall I was quite pleased with the ..."
Reviewed on Aug 3, 2026
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.
The Race Mountain House
Sheffield MA
Stay at this vacation home in Sheffield. Enjoy laundry facilities, patios, and in-room fireplaces. Popular attractions Mount Everett State Reservation and Drury ...
9.6/10 Exceptional! (7 reviews)
"We had a wonderful 2-day stay at this charming house! The location is perfect, nestled near the mountains with breathtaking views. The house itself is clean and cozy, with comfortable bedrooms stocked with extra blankets and pillows. The spacious bathrooms (both upstairs and downstairs!) had plenty ..."
Reviewed on Jan 3, 2026
Antique Farmhouse Totally Restored
Sheffield MA
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Mount Riga State Park and ...
9.8/10 Exceptional! (99 reviews)
"Amazing home in an awesome location. Lots to do close by. Property is interesting, spacious, and convenient. Host is excellent. Our new go to in the Berkshires."
Reviewed on Jul 12, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,041 reviews)
"It would have been the perfect place if the concert at Tanglewood had not been postponed. The checkin went well, the rooms were spacious and clean, and the location was good. Plenty of parking and there are plenty of restaurants nearby for lunch or dinner. Overall I was quite pleased with the ..."
Reviewed on Aug 3, 2026
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.
Stay near popular Sheffield attractions
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- Visit Middlefield
- Visit Springfield
- Visit Dalton
- Visit Lenox
- Visit South Egremont
- Visit Chester
- Visit Hancock
- Visit Tyringham
- Visit The Berkshires
- Visit Otis
- Visit Lee
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- Umpachene Falls Park
- Visit Richmond
- Visit West Stockbridge
- Ski Butternut
- Les Trois Emme Winery
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- Visit Russell
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- Questing
- Visit Alford
- Visit Hinsdale
- Visit Mill River
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- Visit Southfield
- Visit South Lee
- Magnolia Bluffs Casino
- Visit Sandisfield
- Magnolia Bluffs Casino
- Tanglewood Music Center
- National Shrine of the Divine Mercy
- Lime Rock Park
- Norman Rockwell Museum
- Lee Premium Outlets
- Jacob's Pillow
- Taconic State Park
- Ski Butternut
- Kent Falls State Park
- Mohawk Mountain Ski Area
- Lake Taghkanic State Park
- The Mount
- Catamount Ski Area
- Bousquet Ski Area
- Harlem Valley Rail Trail
- Catamount Aerial Adventure Park
- Lenox Library
- Otis Reservoir
- Berkshire Botanical Garden
- Naumkeag Museum
- Infinity Music Hall and Bistro
- Mahaiwe Performing Arts Center
- Wyndhurst Golf & Club
- Burr Pond State Park