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Chestertown Hotels

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Where to stay in Chestertown

Chestertown overview

You can take in the local culture of Chestertown at Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. While you're here, stop by Wilmer Park and Rolphs Wharf Marina. Chestertown is an inviting destination that has something for everyone.

Where to stay in Chestertown

Whether you're planning to stay for a night or a week, Chestertown has accommodations to fit your needs. There are 9 hotels in Chestertown and you can shop as many as 61 deals for rooms on, some with discounts of up to 35%. We have room prices as low as 51 USD per night and below are the number of hotels by star rating in Chestertown as well as in the surrounding area:
  • • 5 4-star hotels from 135 USD per night
  • • 37 3-star hotels from 89 USD per night
  • • 20 2-star hotels from 53 USD per night

How to get to Chestertown

Fly into Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), 30.8 mi (49.6 km) from the heart of Chestertown.

What to see around Chestertown

Fun activities such as boating, horseback riding, and sporting events are at hand, along with attractions such as:
  • • Rolphs Wharf Marina
  • • Rock Hall Harbor
  • • Essex Marina
  • • Freestate Gun Range
  • • Wye Landing
A top draw is the area's festivals, as well as places like:
  • • Garfield Center for the Arts at the Prince Theater
  • • Historical Society of Kent County Maryland
  • • The Mainstay
  • • Mount Harmon Plantation
  • • Cal Ripken Museum
Take some time to explore campus or the area surrounding:
  • • River Arts Chestertown
  • • Washington College
Some recommended sights include:
  • • Wilmer Park
  • • Rolphs Wharf Marina

When to visit Chestertown

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

Seasonal temperature averages
  • • January-March: 58°F day, 25°F night
  • • April-June: 85°F day, 39°F night
  • • July-September: 87°F day, 53°F night
  • • October-December: 73°F day, 28°F night
Seasonal rainfall averages
  • • January-March: 0.31 inches
  • • April-June: 0.35 inches
  • • July-September: 0.43 inches
  • • October-December: 0.31 inches