Chestertown, MD

Travel Guide

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA
Aerial view of historic chestertown near annapolis situated on the chesapeake bay during an early november afternoon
Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA
boats on the river
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road Chestertown MD
The price is ￥17,532 per night from Jun 23 to Jun 24
￥17,532
￥19,461 total
Jun 23 - Jun 24
includes taxes & 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! (918 reviews)
"I stayed here for 5 days and 4 nights housekeeping did not check my room once I never got new towels trash was never collected even when there was 2 adults and 3 kids in one room. Also The water pressure was not the best"

Reviewed on Jun 1, 2026

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
The price is ￥11,466 per night from Jun 8 to Jun 9
￥11,466
￥12,727 total
Jun 8 - Jun 9
includes taxes & 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! (450 reviews)
"The price was very good. The room was clean and spacious. There were a few maintenance issues. Several light bulbs were burned out, the hair dryer did not work, the closet door was off its track, and the Satellite TV was not working. The staff were helpful but unsuccessful in programming the TV. ..."

Reviewed on Jun 1, 2026

Red Roof Inn & Suites Chestertown
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 out of 5
22170 Great Oak Landing Rd Chestertown MD
The price is ￥21,071 per night from Jun 4 to Jun 5
￥21,071
￥24,092 total
Jun 4 - Jun 5
includes taxes & fees
Book a stay at this beach lodge in Chestertown. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
7.8/10 Good! (83 reviews)
"There is a pool but no life guard. The restaurant is closed. No breakfast. You have to make your own coffee. The room was clean but a little damp. Nobody in the office after 5. The beds were comfortable, the view of the sunset over the bay was fabulous. We got carry-out and ate at the outdoor seating. ..."

Reviewed on May 28, 2026

The Lodge at Great Oak Landing
See all 1,091 properties in Chestertown
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.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

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! (22 reviews)
"Lovely cabin in the woods! Nice water access and quiet surrounding."

Reviewed on May 18, 2026

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

Pasadena MD
Stay at this apartment in Pasadena. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Fort Smallwood Park and Compass Pointe Golf Courses ...
9.8/10 Exceptional! (77 reviews)
"Beautiful property, so close to the water and the view is stunning."

Reviewed on May 21, 2026

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Chesapeake Houseboat Getaway on Kent Island, Maryland

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! (57 reviews)
"Such a cool experience"

Reviewed on May 24, 2026

Chesapeake Houseboat Getaway on Kent Island, Maryland
See all properties in Chestertown
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

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.

Washington College

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.

Chestertown Historic District

River Arts Chestertown

Explore the campus of River Arts Chestertown, during your travels in Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown

Rolphs Wharf Marina

Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.

Rolphs Wharf Marina

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.

Historical Society of Kent County Maryland

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.

Wilmer Park

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