Chestertown Travel Guide

Tourist Guide

Photo by Assya A
Photo by Assya A
Photo by Patricia Knorr
Photo by Patricia Knorr
Photo by Patricia Knorr
Photo by Patricia Knorr
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is ฿3,704 per night from 4 Aug to 5 Aug
฿3,704
฿4,112 total
4 Aug - 5 Aug
includes taxes & fees
Stay at this business-friendly hotel in Chestertown. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (775 reviews)
"Smokers smoking at parking lot entry."

Reviewed on 1 Jul 2025

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 ฿2,213 per night from 16 Jul to 17 Jul
฿2,213
฿2,456 total
16 Jul - 17 Jul
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff in their reviews. Popular attractions ...
7.2/10 Good! (369 reviews)
"Great"

Reviewed on 24 Jun 2025

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 ฿4,280 per night from 8 Jul to 9 Jul
฿4,280
฿4,751 total
8 Jul - 9 Jul
includes taxes & fees
Stay at this 3.5-star beach lodge in Chestertown. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Pooles Island Light and Kinnairds Point ...
7.8/10 Good! (52 reviews)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"

Reviewed on 22 Jun 2025

The Lodge at Great Oak Landing
See all 1,079 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.
Majestic Hotel & Apartments
Majestic Hotel & Apartments
3 out of 5
7th St & Boardwalk, Ocean City, MD
Stay at this 3-star beach aparthotel in Ocean City. Enjoy free Wi-Fi, an outdoor pool and parking (surcharge). Our guests praise the helpful staff in their reviews. ...
6.4/10 (222 reviews)
"Ocean front & boardwalk"

Reviewed on 2 Jul 2025

Majestic Hotel & Apartments
Coconut Malorie Resort Hotel, Ascend Hotel Collection
Coconut Malorie Resort Hotel, Ascend Hotel Collection
3 out of 5
200 59th Street on the Bay, Ocean City, MD
Stay at this 3-star aparthotel in Ocean City. Enjoy free Wi-Fi, an outdoor pool and a fitness centre. Our guests praise the helpful staff in their reviews. Popular ...
7.4/10 Good! (1,246 reviews)
"loved saying here at this lovely location!"

Reviewed on 24 Jun 2025

Coconut Malorie Resort Hotel, Ascend Hotel Collection
WhyHotel by Placemakr Columbia
WhyHotel by Placemakr Columbia
4 out of 5
6200 Valencia Ln, Columbia, MD
Stay at this 4-star aparthotel in Columbia. Enjoy free Wi-Fi, a fitness centre and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (730 reviews)
"Great place to stay"

Reviewed on 25 Jun 2025

WhyHotel by Placemakr Columbia
See all 14,401 properties in Maryland
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

Enjoy the student vibe when you visit Washington College during your travels in Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Washington College

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 browsing the exhibits at Historical Society of Kent County Maryland during your trip to Chestertown. Amble around this family-friendly area's riverfront or experience its festivals.

Historical Society of Kent County Maryland

River Arts Chestertown

Enjoy the student vibe when you visit River Arts Chestertown during your trip to Chestertown. Take in the festivals in this family-friendly area.

River Arts Chestertown

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

Chestertown Dog Park

Chestertown Dog Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.

Chestertown Dog Park