Visit Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
$178 nightly
The price is $199 total per night from Jan 28 to Jan 29
$199 total
Jan 28 - Jan 29
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! (42 reviews)
It was a very pleasant hybrid of a classic BnB with the privacy of an air BnB. Host was on point and communicative. We loved hanging out downstairs in the living room(s). Breakfast was fabulous
Reviewed on Jan 14, 2026
Guesthouse Cabin vacation rentals in Berkshire County
Sheffield MA
$621 nightly
The price is $694 total per night from Jan 21 to Jan 22
$694 total
Jan 21 - Jan 22
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)
This was exactly what we were looking for. The property was magnificent the cabin cozy, fully stocked. We plan on coming back soon.
Reviewed on Aug 27, 2025
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)
This was exactly what we were looking for. The property was magnificent the cabin cozy, fully stocked. We plan on coming back soon.
Reviewed on Aug 27, 2025
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 Ponds at Foxhollow
3 Foxhollow Drive Route 7 Lenox MA
Stay at this condo in Lenox. Enjoy free WiFi, free parking, and a fitness center. Popular attractions The Mount and Wyndhurst Golf & Club are located ...
8.4/10 Very Good! (139 reviews)
Condo was a great space. Bathroom walls should be repainted as stains are evident. There were also stains on the couch which I cleaned.
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.
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.
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.
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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