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 ฿3,689 per night from 10 Aug to 11 Aug
฿3,689
฿4,094 total
10 Aug - 11 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! (779 reviews)
"We have stayed with this Comfort Inn, Chestertown, MD location in the past. Breakfast is handy, nearby grocery store and eateries are convenient. Farmers Market on Saturday and trendy Mom & Pop shops are close by. The staff are efficient and ice machines are abundant along with a washer/dryer (coins ..."

Reviewed on 5 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 ฿2,228 per night from 23 Jul to 24 Jul
฿2,228
฿2,474 total
23 Jul - 24 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! (373 reviews)
"Pretty decent room size. AC didn't work very well, but we survived. Good experience overall."

Reviewed on 9 Jul 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 ฿4,296 per night from 17 Jul to 18 Jul
฿4,296
฿4,768 total
17 Jul - 18 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! (53 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 (236 reviews)
"I've stayed with the majestic several times in the past. It's a good apartment rental for me because I don't spend a lot of time inside. It's a little dated but they keep it clean. And I'm normally just looking for somewhere to sleep, shower, and charge my phone. The air conditioning was not very ..."

Reviewed on 9 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! (1,250 reviews)
"Nice place, everyone was nice, service was quick. You did have to pay $15 a day for parking which I think is very unnecessary. But the hotel was located in a nice place. Room was clean. Nice view. Over priced for the stay but it was also 4th July week & busy."

Reviewed on 6 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! (736 reviews)
"Great location and service."

Reviewed on 13 Jul 2025

WhyHotel by Placemakr Columbia
See all 14,419 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