Visit Sheffield
Wilder House Berkshires
48 S Main Street Sheffield MA
$151 nightly
The price is $169 total per night from Dec 30 to Dec 31
$169 total
Dec 30 - Dec 31
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! (41 reviews)
The place is lovely, room is cozy, and the bed is comfy
Reviewed on Dec 22, 2025
The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd Lenox MA
$93 nightly
The price is $103 total per night from Jan 4 to Jan 5
$103 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,000 reviews)
The bed was very comfortable. The staff was helpful and courteous
Reviewed on Dec 24, 2025
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$108 nightly
The price is $120 total per night from Jan 25 to Jan 26
$120 total
Jan 25 - Jan 26, 2026
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! (795 reviews)
Very professional service. Great staff.
Reviewed on Dec 22, 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.
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! (60 reviews)
Remarkable house! I'm still agape at the beauty of the spalted maple woodwork in the kitchen and front area of the place! Plenty of wood for the stoves kept us really warm. Feeding your Highland cows was a highlight for the little folks!
Reviewed on Dec 5, 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! (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
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 ...
8.6/10 Excellent! (136 reviews)
As others have said, it’s extremely well kept and clean. In the Condo and the common areas…immaculate actually. It’s very dated. It would have been nice to know we would have people above us, and the hot tub no longer exists and that was disappointing. It’s a great location and condo is well equipped. ...
Reviewed on Dec 7, 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.
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.
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.
Thom Reed UFO Monument Park
Explore the great outdoors at Thom Reed UFO Monument Park, a lovely green space in 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.
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.
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- Berkshire Botanical Garden
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- Goose Pond Reservation
