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 Feb 18 to Feb 19
$208 total
Feb 18 - Feb 19
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
$621 nightly
The price is $694 total per night from Feb 9 to Feb 10
$694 total
Feb 9 - Feb 10
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! (9 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
Antique Farmhouse Totally Restored
Sheffield MA
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Mount Riga State Park ...
9.6/10 Exceptional! (62 reviews)
We had a great stay. There is lots of room to spread out for a larger group. The furnishings and decorations are wonderful and eccentric, and the property has a rich history, very tastefully preserved. The kids loved the room with gymnastic rings and feeding the highland cattle across the road. Overall, ...
Reviewed on Dec 27, 2025
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.
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! (9 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
Antique Farmhouse Totally Restored
Sheffield MA
Book a stay at this family-friendly vacation home in Sheffield. Enjoy free WiFi, a water park, and a fitness center. Popular attractions Mount Riga State Park ...
9.6/10 Exceptional! (62 reviews)
We had a great stay. There is lots of room to spread out for a larger group. The furnishings and decorations are wonderful and eccentric, and the property has a rich history, very tastefully preserved. The kids loved the room with gymnastic rings and feeding the highland cattle across the road. Overall, ...
Reviewed on Dec 27, 2025
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 ...
9.4/10 Exceptional! (6 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
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.
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.
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.
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.
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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- Naumkeag Museum
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- Housatonic River Walk
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- Lenox Library
