Sheffield, MA
Travel Guide
Visit Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
$218 nightly
The price is $244 total per night from Aug 13 to Aug 14
$244 total
Aug 13 - Aug 14
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
Fully refundableReserve now, pay when you stay
$158 nightly
The price is $176 total per night from Aug 10 to Aug 11
$176 total
Aug 10 - Aug 11
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! (1,016 reviews)
"The staff were friendly, helpful with finding restaurants and other local attractions. Our room was immaculate and nicely furnished with modern furnishings in great condition. The room was quiet--we never heard our neighbors. It was pleasant to sit on the balcony and read. The location is great, ..."
Reviewed on Aug 9, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$125 nightly
The price is $139 total per night from Aug 31 to Sep 1
$139 total
Aug 31 - Sep 1
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! (1,054 reviews)
"Some rooms could use “freshening”"
Reviewed on Aug 8, 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 ...
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
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! (1,054 reviews)
"Some rooms could use “freshening”"
Reviewed on Aug 8, 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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- Cottages in South Egremont
- Great Barrington Hotels
- Cottages in Ashley Falls
- Cabin Rentals in South Egremont
- Inns in Ashley Falls
- Resorts & Hotels with Spas in South Egremont
- Resorts in The Berkshires
- Hotels near Tanglewood Music Center
- Inns in Sheffield
- Lenox Hotels
- Stockbridge Hotels
- Resorts & Hotels with Spas in Great Barrington
- Springfield Hotels
- Mill River Hotels
- B&B in New Marlborough
- 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
- 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
