Hotels in Chestertown, New York

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Best hotels in Chestertown

Chestertown overview

Whatever your interests are, Chestertown has something for you. Chestertown might not have many attractions within the city, but you won't need to venture far to find places to visit like Pack Demonstration Forest and Natural Stone Bridge and Caves. You can take some time to discover the surrounding area and sights like Tannery Pond Community Center and North Creek Ski Bowl Town Park.

Where to stay in Chestertown

Whether you're planning a longer vacation or a weekend getaway, Chestertown has the right accommodation for you. There are 8 hotels in Chestertown and you can shop as many as 127 deals for rooms on, some with discounts of up to 35%. We have room prices starting at 49 USD per night and below are the number of hotels by star rating in Chestertown as well as in the surrounding area:
  • • 14 4-star hotels from 93 USD per night
  • • 65 3-star hotels from 69 USD per night
  • • 39 2-star hotels from 51 USD per night

What to see around Chestertown

Here are some recommended places to see in the surrounding area:
  • • Pack Demonstration Forest (5.9 mi/9.4 km from the city center)
  • • Natural Stone Bridge and Caves (7.7 mi/12.3 km from the city center)
  • • Tannery Pond Community Center (9 mi/14.5 km from the city center)
  • • North Creek Ski Bowl Town Park (9 mi/14.6 km from the city center)
  • • Gore Mountain Ski Resort (9.3 mi/14.9 km from the city center)

When to visit Chestertown

If you're just starting to think about trip planning, you may be curious about the best time to visit. Here are the seasonal norms to help you decide when to go:

Seasonal temperature averages
  • • January-March: 49°F day, 6°F night
  • • April-June: 80°F day, 27°F night
  • • July-September: 81°F day, 40°F night
  • • October-December: 64°F day, 10°F night
Seasonal rainfall averages
  • • January-March: 7.99 inches
  • • April-June: 10.16 inches
  • • July-September: 11.14 inches
  • • October-December: 9.84 inches