Sheffield, MA
Travel Guide
Visit Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
The price is $231 total per night from Sep 13 to Sep 14
$231 total
per night
Sep 13 - Sep 14
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 ...
9.8/10 Exceptional! (62 reviews)
"Breakfast was delicious and everyone was so nice there."
Reviewed on Aug 18, 2026
The Yankee Inn
461 Pittsfield Rd Lenox MA
The price is $170 total per night from Sep 27 to Sep 28
$170 total
per night
Sep 27 - Sep 28
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! (1,022 reviews)
"Charming hotel with a wonderful breakfast and two lovely pools, plus a nature walk to a lake. The staff were great, really nice and helpful."
Reviewed on Aug 26, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is $139 total per night from Aug 31 to Sep 1
$139 total
per night
Aug 31 - Sep 1
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! (1,094 reviews)
"We were very happy with how large the rooms were and it felt like you were in an apartment great location and very clean excellent customer service at the front desk"
Reviewed on Aug 26, 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.
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 ...
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
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! (1,094 reviews)
"We were very happy with how large the rooms were and it felt like you were in an apartment great location and very clean excellent customer service at the front desk"
Reviewed on Aug 26, 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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- Springfield Hotels
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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
- Visit New Marlborough
- Visit Monterey
- Visit Blandford
- Visit Granville
- Visit Housatonic
- Visit Great Barrington
- Umpachene Falls Park
- Visit Richmond
- Visit West Stockbridge
- Ski Butternut
- Les Trois Emme Winery
- Visit Becket
- Visit Berkshire County
- Visit Russell
- Visit Stockbridge
- Questing
- Visit Alford
- Visit Hinsdale
- Visit Mill River
- Visit Pittsfield
- Visit Southfield
- Visit South Lee
- Magnolia Bluffs Casino
- Visit Sandisfield
- Tanglewood Music Center
- Lime Rock Park
- National Shrine of the Divine Mercy
- Lee Premium Outlets
- Norman Rockwell Museum
- Ski Butternut
- Jacob's Pillow
- Taconic State Park
- The Mount
- Mohawk Mountain Ski Area
- Kent Falls State Park
- Lake Taghkanic State Park
- Bousquet Ski Area
- Catamount Ski Area
- Lenox Library
- Mahaiwe Performing Arts Center
- Naumkeag Museum
- Infinity Music Hall and Bistro
- Wyndhurst Golf & Club
- Otis Reservoir
- Shakespeare and Company
- Catamount Aerial Adventure Park
- Berkshire Botanical Garden
- Music Mountain
- Otis Ridge
