Chestertown, MD

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
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd, Chestertown, MD
The price is NT$2,244 per night from Aug 3 to Aug 4
NT$2,244
NT$2,491 total
Aug 3 - Aug 4
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! (379 reviews)
SweetyPie The Explorer from Florida
"Our check-in quicl Staff was quick. The rooms have a very spacious area it was clean and the beds were comfortable just for a night to crash."

Reviewed on 2025/7/21

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 NT$3,371 per night from Aug 17 to Aug 18
NT$3,371
NT$3,742 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! (785 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 2025/7/18

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 NT$3,881 per night from Aug 24 to Aug 25
NT$3,881
NT$4,308 total
Aug 24 - Aug 25
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 ...
7.8/10 Good! (55 reviews)
Getaway
"We love this place….awesome pool,and free golf….couldn’t ask for more 😃"

Reviewed on 2025/7/15

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 WiFi, an outdoor pool, and parking (surcharge). Our guests praise the helpful staff in our reviews. ...
6.4/10 (250 reviews)
Great Stay!!!
"Really enjoyed my time at Majestic hotel in Ocean City MD The staff was so nice and they were very helpful."

Reviewed on 2025/7/16

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! (1,256 reviews)
"So nice and roomy! Loved this hotel!"

Reviewed on 2025/7/18

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! (743 reviews)
Great place to stay for concerts
"Really comfortable stay and perfect for Merriweather Pavilion. We will be back!"

Reviewed on 2025/7/20

WhyHotel by Placemakr Columbia
See all 14,442 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

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.

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