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
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
The price is Rp1.251.698 per night from 11 Aug to 12 Aug
Rp1.251.698
Rp1.389.385 total
11 Aug - 12 Aug
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! (383 reviews)
"Did not like lack of vending services"

Reviewed on 28 Jul 2025

Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 out of 5
150 Scheeler Road, Chestertown, MD
The price is Rp1.802.693 per night from 3 Aug to 4 Aug
Rp1.802.693
Rp2.000.913 total
3 Aug - 4 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! (787 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 18 Jul 2025

Comfort 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 Rp2.170.911 per night from 3 Aug to 4 Aug
Rp2.170.911
Rp2.409.826 total
3 Aug - 4 Aug
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! (56 reviews)
Getaway
"We love this place….awesome pool,and free golf….couldn’t ask for more 😃"

Reviewed on 15 Jul 2025

The Lodge at Great Oak Landing
See all 1,078 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. ...
6.2/10 (256 reviews)
"Overall good experience thank you for having us!"

Reviewed on 26 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! (1,259 reviews)
"Food was okay not great from the local restaurants The bed was quite comfortable"

Reviewed on 28 Jul 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! (747 reviews)
Great place to stay for concerts
"Really comfortable stay and perfect for Merriweather Pavilion. We will be back!"

Reviewed on 20 Jul 2025

WhyHotel by Placemakr Columbia
See all 14,463 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

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

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

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