Sheffield, MA
Travel Guide
Visit Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
$128 nightly
The price is $143 total per night from Mar 29 to Mar 30
$143 total
Mar 29 - Mar 30
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! (43 reviews)
Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back.
Reviewed on Jan 23, 2026
Luxury Private Estate in the Berkshires | Whitney by AvantStay
Sheffield MA
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Thom Reed UFO Monument ...
8.6/10 Excellent! (14 reviews)
Great quiet house.
Reviewed on Oct 17, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$121 nightly
The price is $135 total per night from Mar 26 to Mar 27
$135 total
Mar 26 - Mar 27
Total with taxes and fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (885 reviews)
very clean and friendly staff
Reviewed on Mar 24, 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! (96 reviews)
Robin was a kind host! The house is a beautiful place to stay; the pantry and bookshelves were stocked, and the house has historic charm. The kids loved feeding the cows and looking at all of the decor.
Reviewed on Feb 16, 2026
Luxury Private Estate in the Berkshires | Whitney by AvantStay
Sheffield MA
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Thom Reed UFO Monument ...
8.6/10 Excellent! (14 reviews)
Great quiet house.
Reviewed on Oct 17, 2025
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield MA
Stay at this cabin in Sheffield. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Mount Everett State Reservation and Plaintain Pond ...
10/10 Exceptional! (10 reviews)
We were a group of moms who snuck away for the night and this cabin was the perfect retreat. Well stocked and very cozy on a winter night. We had to leave very early the next morning to beat a snowstorm and the very long driveway was already sanded and we felt very safe. Lisette was great to work ...
Reviewed on Jan 29, 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.
Popular places to visit
Magnolia Bluffs Casino
Why not roll the dice with a visit to Magnolia Bluffs Casino during your travels in Sheffield? Discover the area's breweries or seek out the hiking trails.
Lime Kiln Farm Wildlife Sanctuary
You can take time to visit Lime Kiln Farm Wildlife Sanctuary during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
Ashley House
You can learn about the history of Sheffield with a trip to Ashley House. Discover the area's breweries or seek out the hiking trails.
Bartholomew's Cobble
You can take time to visit Bartholomew's Cobble during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
Drury Preserve
You can take time to visit Drury Preserve during your travels to Sheffield. Make some time to visit the casinos while you're in the area.
Bartholomews Cobble
Explore the great outdoors at Bartholomews Cobble, a lovely green space in Sheffield. Make some time to visit the casinos while you're in the area.
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- Magnolia Bluffs Casino
- Tanglewood Music Center
- National Shrine of the Divine Mercy
- Norman Rockwell Museum
- Lime Rock Park
- Ski Butternut
- Mohawk Mountain Ski Area
- Catamount Ski Area
- The Mount
- Lee Premium Outlets
- Jacob's Pillow
- Bousquet Ski Area
- Catamount Aerial Adventure Park
- Kent Falls State Park
- Mohawk Mountain State Forest
- Mahaiwe Performing Arts Center
- Naumkeag Museum
- Taconic State Park
- Wyndhurst Golf & Club
- Berkshire Botanical Garden
- Shakespeare and Company
- Ventfort Hall Mansion and Gilded Age Museum
- Infinity Music Hall and Bistro
- Harlem Valley Rail Trail
