Chestertown

Travel 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 P6,378 per night from Aug 17 to Aug 18
P6,378
P7,079 total
Aug 17 - Aug 18
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 ...
8.4/10 Very Good! (788 reviews)
"Service was great all the staff we came in contact with were kind and helpful from showing us how to work the TV to giving us bottled water when the drink vending machine was out. We enjoyed our stay and the location was very close to Chestertown and Rock Hall."

Reviewed on Jul 18, 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 P4,188 per night from Aug 10 to Aug 11
P4,188
P4,648 total
Aug 10 - Aug 11
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! (384 reviews)
"Great service"

Reviewed on Aug 1, 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 P7,695 per night from Aug 4 to Aug 5
P7,695
P8,542 total
Aug 4 - Aug 5
includes taxes & fees
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 ...
8/10 Very Good! (57 reviews)
Great staff
"Staff was very helpful in dealing with some confusion at check in. Every on went above and beyond to deal with the situation and was very welcoming during the process."

Reviewed on Jul 28, 2025

The Lodge at Great Oak Landing
See all 1,076 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 WiFi, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff in our reviews. ...
6.2/10 (269 reviews)
"Staff excellent. Room ready early. Loud at night until 11:45p.m. Older hotel w/ thin walls. Small parking lot. Tiny elevator. Many food options and shopping. On boardwalk. Easy beach access close by."

Reviewed on Aug 1, 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 WiFi, an outdoor pool, and a fitness center. Our guests praise the helpful staff in our reviews. Popular ...
7.4/10 Good! (1,261 reviews)
"This is a wonderful property. I will be going back and I recommend everybody check it out as well!"

Reviewed on Jul 30, 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 WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (749 reviews)
"Floyd at checkin was absolutely amazing. Clean rooms and it's a quick walk to the concert venue! Thanks for a great stay"

Reviewed on Jul 30, 2025

WhyHotel by Placemakr Columbia
See all 14,462 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

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

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

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

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

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