5/5 - Excellent
Krista
Chestertown is a beautiful place.
Visit Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD
Book a stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Red Roof Inn & Suites Chestertown
160 Scheeler Rd, Chestertown, MD
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions ...
The Lodge at Great Oak Landing
22170 Great Oak Landing Rd, Chestertown, MD
Stay at this 3.5-star beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Washington College
Take a campus tour or just explore the area of Washington College, during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
Historical Society of Kent County Maryland
You can spend an afternoon exploring the galleries in Historical Society of Kent County Maryland during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Wilmer Park
Wilmer Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Amble around this family-friendly area's riverfront or experience its festivals.
River Arts Chestertown
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
Garfield Center for the Arts at the Prince Theater
You can get tickets for a performance at Garfield Center for the Arts at the Prince Theater on your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.
Reviews of Chestertown
4.1
Top Destination
5/5 - Excellent
Verified traveler
None of the choices Expedia gave me for places I went to were anywhere near Chestertown. Chestertown is a very nice community with wonderful Colonial Houses, a nice harbour, interesting history, and an amazing number of great restaurants.
4/5 - Good
Verified traveler
Definitely the Land of Pleasant Living!
3/5 - Okay
jana
We went to Washington College. Downtown Chestertown was cute.
4/5 - Good
WashDad23
Small attractive college town on the bay, good restaurants, nice period houses
5/5 - Excellent
Verified traveler
We were in Chestertown to visit Washington College. The town is so special and lovely! I would really love to visit when the weather is warmer to enjoy the water and all the offerings in the area.
- Washington College
- Rolphs Wharf Marina
- Historical Society of Kent County Maryland
- Wilmer Park
- River Arts Chestertown
- Garfield Center for the Arts at the Prince Theater
- Crumpton Auction
- Sumner Hall
- Baltimore Cruise Terminal
- U.S. Naval Academy
- Annapolis City Dock
- Chesapeake Bay Bridge
- Sandy Point State Park
- Ripken Stadium
- Navy-Marine Corps Memorial Stadium
- Susquehanna River
- White Marsh Mall
- Cedar Lane Regional Park
- Rock Hall Harbor
- Harford Community College
- Fort McHenry
- Havre de Grace Promenade
- Cal Ripken Museum
- Bohemia Vista Marina