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 RM463 per night from 7 Sept to 8 Sept
RM463
RM514 total
7 Sept - 8 Sept
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! (795 reviews)
"FEELS LIKE PEACEFULLY 👍 👌"

Reviewed on 14 Aug 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 RM303 per night from 25 Aug to 26 Aug
RM303
RM337 total
25 Aug - 26 Aug
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! (386 reviews)
"Great service"

Reviewed on 1 Aug 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 RM559 per night from 20 Aug to 21 Aug
RM559
RM620 total
20 Aug - 21 Aug
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! (61 reviews)
"Perfect place to unwind. Great views of the harbor and marina. You get access to a private beach and there is a cute area for kids to play. The private beach provides chairs and umbrellas. The lodge also has a bar/food on site."

Reviewed on 16 Aug 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. ...
6/10 (299 reviews)
"I reqlly enjoyed my stay!"

Reviewed on 16 Aug 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! (1,274 reviews)
"Only one issue and that was the water pressure in the shower was really bad. Sometimes it would completely shut off for a minutes then comeback on or it will just be real light. Other than had a great time we’ll definitely be going there at our next stay in ocean city"

Reviewed on 13 Aug 2025

Coconut Malorie Resort Hotel, Ascend Hotel Collection
Ocean Terrace Family Apartments

Ocean Terrace Family Apartments

3 out of 5
1211 Baltimore Avenue, Ocean City, MD
Stay at this 3-star apartment in Ocean City. Enjoy free WiFi, free parking, and cable TV channels. Popular attractions Ocean City Boardwalk and Ocean City Beach ...
8.2/10 Very Good! (28 reviews)
Great value
"Check in was easy, parking was available and the staff were very helpful!"

Reviewed on 19 May 2025

Ocean Terrace Family Apartments
See all 14,434 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