Hotels in Cheshire, Connecticut

Search & Compare Cheshire Hotels

  • Pay now or later on most rooms
  • Free cancellation on most rooms
  • Price Guarantee

Best hotels in Cheshire

Cheshire overview

You can easily spend a relaxing day in Cheshire visiting Drazen Orchards and Bartlem Park. While you're here, stop by Maplecroft Plaza Shopping Center and Barker Museum. If you're looking for a new favorite getaway, look no further than Cheshire.

Where to stay in Cheshire

Whether you're planning to stay for a night or for the week, the area around Cheshire has accommodations to fit every need. Search for hotels in Cheshire with by checking our online map. Our maps display the areas and neighborhoods around all Cheshire hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Cheshire hotel deals are here with our lowest price guarantee.

How to get to Cheshire

Fly in to New Haven, CT (HVN-Tweed - New Haven Regional), 16.8 mi (27.1 km) from downtown Cheshire. Hartford, CT (HFD-Hartford - Brainard) is the next closest major airport, 20.6 mi (33.2 km) away.

What to see around Cheshire

Fun activities include attractions such as:
  • • Cromwell Meadows Wildlife Management Area
  • • Black Rock State Park
  • • Brownstone Exploration & Discovery Park
  • • Winding Trails
Family-friendly attractions include:
  • • Drazen Orchards
  • • Cheshire Hollow Farm
  • • CoCo Key Water Resort Hotel & Convention Center - Waterbury
  • • Lake Compounce
  • • Lyman Orchards
Distinguished for its historical sites, here are some top landmarks to visit:
  • • Andrews Homestead Museum
  • • Grove Street Cemetery
  • • Harts Corner Historic District
  • • Miss Porter's School
  • • Stanley-Whitman House
It's notable for its waterfalls, hiking trails, and top spots for nature lovers that include:
  • • Bartlem Park
  • • Quinnipiac Recreation Area
  • • Roaring Brook Park
  • • Habershon Field
  • • Panthorn Park
Some popular places in the area include:
  • • East Rock Park
  • • Yale University
  • • Yale Bowl

When to visit Cheshire

Wondering when's the best time to visit? Here are seasonal norms to help you plan your trip:

Seasonal temperature averages
  • January-March: 54°F day, 16°F night
  • April-June: 83°F day, 33°F night
  • July-September: 84°F day, 46°F night
  • October-December: 69°F day, 19°F night
Seasonal rainfall averages
  • January-March: 11.26 inches
  • April-June: 11.54 inches
  • July-September: 12.20 inches
  • October-December: 12.95 inches