Skip to main content.

Hotels in Cheshire, Connecticut

Search & Compare Cheshire Hotels

Save more with Secret Prices

Get instant savings with Secret Prices

  • 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

A welcoming city, Cheshire offers a variety of hotels and other lodging choices. There are 2 hotels in Cheshire and you can shop as many as 243 deals for rooms on, some with discounts of up to 35%. Our room prices start at 45 USD per night and here's a breakdown of hotels by star rating in Cheshire as well as in the surrounding area:
  • • 21 4-star hotels from 122 USD per night
  • • 86 3-star hotels from 79 USD per night
  • • 40 2-star hotels from 50 USD per night

How to get to Cheshire

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

What to see around Cheshire

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 recommended sights include:
  • • Maplecroft Plaza Shopping Center
  • • Barker Museum
  • • Cheshire Hollow Farm

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