5/5 - Excellent
Krista
Chestertown is a beautiful place.
Chestertown, MD
Travel Guide
Visit Chestertown
Comfort Inn & Suites Chestertown
150 Scheeler Road Chestertown MD
$102 nightly
The price is $113 total per night from Mar 22 to Mar 23
$113 total
Mar 22 - Mar 23
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 ...
8.6/10 Excellent! (885 reviews)
Clean room, friendly staff, shops nearby Everything was good
Reviewed on Mar 10, 2026
Historic Inns of Annapolis
58 State Circle Annapolis MD
Fully refundableReserve now, pay when you stay
$157 nightly
The price is $179 total per night from Apr 2 to Apr 3
$179 total
Apr 2 - Apr 3
Total with taxes and fees
Book a stay at this historic hotel in Annapolis. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean ...
9/10 Wonderful! (1,879 reviews)
The elevator was not working the entire time.
Reviewed on Mar 13, 2026
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
4 Philadelphia Ct Rosedale MD
$71 nightly
The price is $82 total per night from Mar 19 to Mar 20
$82 total
Mar 19 - Mar 20
Total with taxes and fees
Book a stay at this business-friendly hotel in Rosedale. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
7/10 Good! (1,175 reviews)
Everything was clean and near
Reviewed on Mar 13, 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.
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
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Chestertown MD
Stay at this cabin in Chestertown. Enjoy a garden, laundry facilities, and patios. Popular attractions Chase Island and Crumpton Auction are located nearby.
10/10 Exceptional! (15 reviews)
We had a perfect stay.
Reviewed on Mar 9, 2026
Chesapeake Houseboat Getaway on Kent Island, Maryland
Stevensville MD
Stay at this houseboat in Stevensville. Enjoy patios, an in-room coffeemaker, and in-room fireplaces. Popular attractions Romancoke Wharf County Park and Matapeake ...
9.8/10 Exceptional! (49 reviews)
This was a terrific experience. The house boat was extremely clean and well taken care of. The host was proactive with terrific communication. She was upfront with the care and expectations of the stay. It was well stocked, perfect for cooking and enjoying the views from the boat. We are already ...
Reviewed on Mar 11, 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.
Popular places to visit
Washington College
4/5(13 reviews)
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.
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.
Rolphs Wharf Marina
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. 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.
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.
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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- Rolphs Wharf Marina
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- Historical Society of Kent County Maryland
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- Rolphs Wharf Marina
- Wilmer Park
- Garfield Center for the Arts at the Prince Theater
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- Baltimore Cruise Terminal
- Chesapeake Bay
- Annapolis City Dock
- Ripken Stadium
- Chesapeake Bay Bridge
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- White Marsh Mall
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- Navy-Marine Corps Memorial Stadium
- CopperPlex
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