5/5 - Excellent
Krista
Chestertown is a beautiful place.
Visit Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
$94 nightly
The price is $104 total per night from Feb 1 to Feb 2
$104 total
Feb 1 - Feb 2
Total with taxes and fees
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 ...
8.4/10 Very Good! (864 reviews)
Very nice
Reviewed on Dec 14, 2025
Red Roof Inn & Suites Chestertown
160 Scheeler Rd Chestertown MD
$72 nightly
The price is $80 total per night from Jan 19 to Jan 20
$80 total
Jan 19 - Jan 20
Total with taxes and fees
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 ...
7.2/10 Good! (426 reviews)
Clean and friendly staff. Good location.
Reviewed on Jan 2, 2026
Pendry Baltimore
1715 Thames St. Baltimore MD
$355 nightly
The price is $417 total per night from Jan 29 to Jan 30
$417 total
Jan 29 - Jan 30
Total with taxes and fees
Book a stay at this luxury hotel in Baltimore. Enjoy free WiFi, an outdoor pool, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. Popular ...
9.2/10 Wonderful! (1,000 reviews)
The hotel was beautiful, and the staff was courteous and friendly.
Reviewed on Jan 5, 2026
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.
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!
Chestertown MD
Stay at this vacation home in Chestertown. Enjoy laundry facilities and air conditioning. Popular attractions Garfield Center for the Arts at the Prince Theater ...
10/10 Exceptional! (2 reviews)
The house is beautiful and cozy. Great location. Short walk to restaurants and shops.
Reviewed on Nov 28, 2025
First Floor Studio Apartment in Historic Chestertown
Chestertown MD
Book a stay at this golf apartment in Chestertown. Enjoy free WiFi, private pools, and a fitness center. Popular attractions Wilmer Park and Sumner Hall are ...
9.6/10 Exceptional! (108 reviews)
Every thing was great
Reviewed on Dec 7, 2025
Hudson house
3037 Hudson St Baltimore MD
Stay at this residence in Baltimore. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Baltimore Inner Harbor Marina and Baltimore Cruise ...
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.
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.
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.
River Arts Chestertown
Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.
Chestertown Historic District
Find out about the history of Chestertown with a stop at Chestertown Historic District. Experience the area's festivals and art scene.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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.
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- Washington College
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- Washington College
- Wilmer Park
- Historical Society of Kent County Maryland
- River Arts Chestertown
- Rolphs Wharf Marina
- Garfield Center for the Arts at the Prince Theater
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- Ripken Stadium
- Chesapeake Bay Bridge
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