Hotels in Chestertown

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Best Chestertown Hotels

Where to stay in Chestertown

Whether you're planning a longer holiday or a weekend getaway, Chestertown has the right hotel for you. There are 10 hotels in Chestertown and you can shop for as many as 92 deals for rooms on, some with discounts of up to 35%. We have room prices starting at GBP 37 per night. Below, you can find the number of hotels by star rating in Chestertown as well as in the surrounding area:
  • • 14 4-star hotels from GBP 71 per night
  • • 65 3-star hotels from GBP 51 per night
  • • 39 2-star hotels from GBP 41 per night

How to get to Chestertown

Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), 23.3 mi (37.5 km) from central Chestertown.

What to see around Chestertown

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

When to visit Chestertown

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

Seasonal temperatures
  • • January-March: 10°F day, -14°F night
  • • April-June: 27°F day, -3°F night
  • • July-September: 27°F day, 5°F night
  • • October-December: 18°F day, -12°F night
Seasonal average rainfall
  • • January-March: 201 inches
  • • April-June: 258 inches
  • • July-September: 283 inches
  • • October-December: 250 inches