Sheffield, MA
Travel Guide
Visit Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
$186 nightly
The price is $208 total per night from Mar 12 to Mar 13
$208 total
Mar 12 - Mar 13
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
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield MA
$616 nightly
The price is $688 total per night from Mar 8 to Mar 9
$688 total
Mar 8 - Mar 9
Total with taxes and fees
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
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
Fully refundable
$115 nightly
The price is $128 total per night from Apr 5 to Apr 6
$128 total
Apr 5 - Apr 6
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! (869 reviews)
The staff at the front desk was welcoming, the room was very nice. We enjoyed our stay. HOWEVER - on the day we were to arrive there was a major blizzard. There was no safe way to drive from the Boston area to Pittsfield. I called the hotel 2 days before to say that we would be arriving a day after ...
Reviewed on Mar 6, 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
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
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
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
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.
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.
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.
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.
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.
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.
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- Magnolia Bluffs Casino
- Tanglewood Music Center
- National Shrine of the Divine Mercy
- Norman Rockwell Museum
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- Mohawk Mountain Ski Area
- Lime Rock Park
- Catamount Ski Area
- Bousquet Ski Area
- Jacob's Pillow
- The Mount
- Lee Premium Outlets
- Catamount Aerial Adventure Park
- Naumkeag Museum
- Kent Falls State Park
- Mohawk Mountain State Forest
- Housatonic River Walk
- Lenox Library
- Ventfort Hall Mansion and Gilded Age Museum
- Macedonia Brook State Park
- Wyndhurst Golf & Club
- Berkshire Botanical Garden
- Mahaiwe Performing Arts Center
