Hotels in Chestertown, Maryland

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Best hotels in Chestertown

Chestertown overview

Chestertown is a budget-friendly place distinct for its rich culture and festivals, and known for its college atmosphere and shops. You'll find extensive seafood and coffee options. Take in some of the area's local culture at Garfield Center for the Arts at the Prince Theater and Historical Society of Kent County Maryland. Be sure stop by Wilmer Park and Washington College while you're here. A family- and business-friendly area, Chestertown also has something for everyone.

Where to stay in Chestertown

Whether you're planning to stay for a night or for the week, Chestertown has accommodations to fit every need. There are 55 hotels in the Chestertown area, some with discounts of up to 15%.
  • • 23 2-star hotels with an average price of $51 per night
  • • 28 3-star hotels with an average price of $80 per night
  • • 3 4-star hotels with an average price of $166 per night

Here are the top hotels based on 5878 user reviews of Chestertown hotels:
  • • John L Stam House (Chestertown)
  • • Holiday Inn Express Hotel & Suites Chestertown (Chestertown)
  • • Quality Suites (Chestertown)
  • • Driftwood Inn (Chestertown)
  • • Simply Bed & Bread (Chestertown)

How to get to Chestertown

Fly in to Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall), 30.8 mi (49.6 km) from downtown Chestertown.

What to see around Chestertown

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
Whether window-shopping or searching for a perfect souvenir, here are some favorite shopping areas:
  • • Queenstown Premium Outlets
  • • White Marsh Mall
Here are some top sights to see:
  • • Wilmer Park
  • • Washington College
  • • Rolphs Wharf Marina
  • • Cassinelli Winery and Vineyards
  • • Rock Hall Harbor

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: 54°F day, 21°F night
  • • April-June: 81°F day, 37°F night
  • • July-September: 83°F day, 51°F night
  • • October-December: 67°F day, 22°F night
Seasonal rainfall averages
  • • January-March: 10.0 inches
  • • April-June: 11.0 inches
  • • July-September: 11.5 inches
  • • October-December: 10.1 inches