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 Sep 27 to Sep 28
$218 total
Sep 27 - Sep 28
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 ...
9.8/10 Exceptional! (66 reviews)
"Brad was very hospitable and helpful with advice on what to do. And the breakfasts were great."
Reviewed on Sep 15, 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 ...
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $121 total per night from Oct 1 to Oct 2
$121 total
Oct 1 - Oct 2
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! (1,152 reviews)
"Kudos to the welcoming and attentive staff. Fast check-in, clean suite, convenient laundry room, quiet area, and less than a 10 minute drive to Tanglewood and restaurants. Hot tub was unavailable but the beverage machine at the lobby was very much appreciated."
Reviewed on Sep 23, 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 ...
8.8/10 Excellent! (9 reviews)
"We had a lot of difficulty with communication with the property manager and until we were on the way, it was unclear we would be able to get in. There were issues with the plumbing and the AC did not work all weekend (in over 100 degree heat). Items throughout the house, such as cabinets and doors, ..."
Reviewed on Sep 4, 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! (1,152 reviews)
"Kudos to the welcoming and attentive staff. Fast check-in, clean suite, convenient laundry room, quiet area, and less than a 10 minute drive to Tanglewood and restaurants. Hot tub was unavailable but the beverage machine at the lobby was very much appreciated."
Reviewed on Sep 23, 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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- Tanglewood Music Center
- Ski Butternut
- Norman Rockwell Museum
- National Shrine of the Divine Mercy
- Lime Rock Park
- Taconic State Park
- Lee Premium Outlets
- Mohawk Mountain Ski Area
- Catamount Ski Area
- Bousquet Ski Area
- Kent Falls State Park
- The Mount
- Jacob's Pillow
- Lake Taghkanic State Park
- Shakespeare and Company
- Naumkeag Museum
- Mahaiwe Performing Arts Center
- Catamount Aerial Adventure Park
- Otis Reservoir
- Music Mountain
- Wyndhurst Golf & Club
- Ventfort Hall Mansion and Gilded Age Museum
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