Sheffield holiday rentals
Find spaces that suit your style
Find the best place to stay - Sheffield
The Playhouse: 7,000 Square Feet of Berkshires Modern Luxury and History
Top rated rentals - Sheffield
Photo gallery for Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly
Wonderful Family Gatherin
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value
The historical area of Sheffield awaits your stay
Enjoy the history and other features of Sheffield. This city is well-known for its casino gaming and local tours. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.
Activities and attractions in and around Sheffield
Are you looking for attractions to see in the area? Venture out of your cosy holiday rental and experience everything that makes Sheffield a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:
- Ski Butternut (5.3 mi / 8.6 km)
- Catamount Ski Area (7.4 mi / 12 km)
- Wyndhurst Golf & Club (16.7 mi / 26.9 km)
- Lake Taghkanic State Park (17.9 mi / 28.8 km)
- Mohawk Mountain Ski Area (19.1 mi / 30.8 km)
- Les Trois Emme Winery (4.9 mi / 8 km)
Exploring the natural landscape of Sheffield
Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Sheffield is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:
- Housatonic River Walk (6 mi / 9.7 km)
- Bash Bish Falls State Park (7 mi / 11.2 km)
- Taconic State Park (8.3 mi / 13.3 km)
- Mount Frissell (9.5 mi / 15.3 km)
- Naumkeag Museum (12.6 mi / 20.2 km)
- Berkshire Botanical Garden (13.2 mi / 21.3 km)
Transport to and around Sheffield
The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 22 mi (35.4 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Hudson, NY (HCC-Columbia County), which is 22.3 mi (35.9 km) away.