Sheffield
Travel Guide
Visit Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
The price is CA $280 per night from Aug 27 to Aug 28
CA $280
CA $313 total
Aug 27 - Aug 28
includes taxes & 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 ...
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 CA $178 per night from Sep 16 to Sep 17
CA $178
CA $198 total
Sep 16 - Sep 17
includes taxes & 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! (1,014 reviews)
"Free Breakfasts were excellent, but the room was tired, bathroom and shower very small"
Reviewed on Aug 20, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
The price is CA $131 per night from Aug 31 to Sep 1
CA $131
CA $178 total
Aug 31 - Sep 1
includes taxes & 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! (1,084 reviews)
"Pleasant place to stay. About 10 minutes from Tanglewood. Alpha centrally located to many things to do in the Berkshire area."
Reviewed on Aug 20, 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! (1,084 reviews)
"Pleasant place to stay. About 10 minutes from Tanglewood. Alpha centrally located to many things to do in the Berkshire area."
Reviewed on Aug 20, 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.
