Discover a selection of 149 vacation rentals in Cheshire that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and private pools. Prices start at $153 per night, and condos and houses are popular options for a stay in Cheshire. Either way, you'll find a rental for everyone's needs.
Top rated rentals — Cheshire
Destination guide

Take in the lakeside beauty of Cheshire

The lake and wildlife create a pretty picture of Cheshire. Well known for its skiing, hiking and restaurants, this romantic city won't disappoint. Many of our vacation rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.


Activities and attractions in Cheshire

Do you want to discover things to do while you're in town? Venture out of your cozy vacation rental and check out everything that makes Cheshire a fun place to get away. These are some of the top attractions to explore, all within 30 miles (48.2 km) of the city center:

  • Waubeeka Golf Links (7.9 mi / 12.7 km)
  • Bas Ridge Golf Course (8.6 mi / 13.8 km)
  • Bousquet Ski Area (11.7 mi / 18.9 km)
  • Clarksburg State Park (12.4 mi / 20 km)
  • Hawley Bog Preserve (13.9 mi / 22.3 km)
  • Kennedy Park (14 mi / 22.5 km)
Natural features

Exploring the natural landscape of Cheshire

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, you'll be sure to find the perfect setting for your vacation in Cheshire. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city center:

  • Mount Greylock State Reservation Visitor Center (3.2 mi / 5.1 km)
  • Mount Greylock (5.2 mi / 8.4 km)
  • Wahconah Falls State Park (5.4 mi / 8.7 km)
  • Savoy Mountain State Forest (7.5 mi / 12.1 km)
  • Windsor Lake Park (9.1 mi / 14.6 km)
  • Western Gateway Heritage State Park (9.4 mi / 15.1 km)
How to get there

Transportation to and around Cheshire

Fly into Pittsfield, MA (PSF-Pittsfield Municipal), the closest airport, located 11.9 mi (19.1 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Hudson, NY (HCC-Columbia County), which is 34.1 mi (54.8 km) away.

How many vacation rentals are available around Cheshire?

Our 2021 property listings offer a large selection of 149 vacation rentals around Cheshire. From 48 condo and apartment rentals to 82 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.