Visit Sheffield
Wilder House Berkshires
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!
Reviewed on 10 November 2025
Antique Farmhouse Totally Restored
Our group of 8 had a delightful stay at the Antique Farmhouse! Robin was very friendly and responsive. It’s a large house, with plenty of room to spread out and explore. The kitchen is large, and very well equipped. We enjoyed cooking meals together as a group. The property itself is beautiful, and ...
Reviewed on 16 October 2025
Berkshire Mountain Lodge
When we are out in Pittsfield we always stay at the BML. The rooms are spacious, clean, and comfortable. For the price of a hotel room, you get a small condo. The staff is always friendly and helpful. Stay there, you won't regret it.
Reviewed on 26 November 2025
Antique Farmhouse Totally Restored
Our group of 8 had a delightful stay at the Antique Farmhouse! Robin was very friendly and responsive. It’s a large house, with plenty of room to spread out and explore. The kitchen is large, and very well equipped. We enjoyed cooking meals together as a group. The property itself is beautiful, and ...
Reviewed on 16 October 2025
Guesthouse Cabin vacation rentals in Berkshire County
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 27 August 2025
The Ponds at Foxhollow
Very good value
Reviewed on 18 November 2025
Popular places to visit
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.
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.
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.
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.
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
- Magnolia Bluffs Casino
- Tanglewood Music Center
- Ski Butternut
- Catamount Ski Area
- Mohawk Mountain Ski Area
- National Shrine of the Divine Mercy
- Bousquet Ski Area
- Lee Premium Outlets
- Lime Rock Park
- Norman Rockwell Museum
- The Mount
- Jacob's Pillow
- Kent Falls State Park
- Mahaiwe Performing Arts Center
- Taconic State Park
- Catamount Aerial Adventure Park
- Naumkeag Museum
- Mohawk Mountain State Forest
- Goose Pond Reservation
- Infinity Music Hall and Bistro
- Berkshire Botanical Garden
- Highland Lake
- Housatonic River Walk
- Music Mountain
- Lenox Library
