Chestertown, MD

Travel Guide

Quaint Chestertown awaits: its sports, university life, boating, and more!

Venture to sights like Rolphs Wharf Marina and Historical Society of Kent County Maryland as you discover Chestertown—a city also notable for its college vibe.

Driftwood Inn
Driftwood Inn
2 out of 5
609 Washington Avenue, Chestertown, MD, 21620
The price is $80 per night from May 18 to May 19
Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the WiFi and the bathrooms in our reviews. Discover ...
2.3/5 (141 reviews)
Hunting weekend excursion
"Staff was courteous and responsive Rooms met expectations Our hunting party of 2 adults and 2 youths were comfortable Throughout our stay."

Reviewed on Nov 15, 2021

Driftwood Inn
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 out of 5
150 Scheeler Road, Chestertown, MD, 21620
The price is $127 per night from May 24 to May 25
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 rooms ...
4.2/5 Excellent! (531 reviews)
"Nice area lots of food options"

Reviewed on Apr 19, 2022

Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2 out of 5
160 Scheeler Rd, Chestertown, MD, 21620
Fully refundableReserve now, pay when you stay
The price is $129 per night from Jun 6 to Jun 7
Stay at this business-friendly hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Discover genuine guest reviews for Red Roof Inn ...
3.8/5 Good! (151 reviews)
Ok stay
"Place was as expected. Room was clean. Plenty of parking. Service was ok. I thought the price was a little high for the location and location of the place."

Reviewed on Dec 20, 2021

Red Roof Inn & Suites 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.
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic Chestertown
Chestertown, MD
The price is $110 per night from May 18 to May 19
Stay at this golf apartment in Chestertown. Enjoy free WiFi, an outdoor pool, and a fitness center. Discover genuine guest reviews for First Floor Studio Apartment ...
5/5 Exceptional! (2 reviews)
Lovely stay in Chestertown
"Only stayed for one night but would definitely enjoy more. Amazing family with hospitality that went above and beyond.. Close to town and a nice escape."

Reviewed on Apr 4, 2022

First Floor Studio Apartment in Historic Chestertown
Carriage House Hideaway in Middle of Chestertown
Carriage House Hideaway in Middle of Chestertown
Chestertown, MD
The price is $125 per night from Jun 13 to Jun 14
Stay at this family-friendly apartment in Chestertown. Enjoy free WiFi, onsite parking, and a garden. Discover genuine guest reviews for Carriage House Hideaway ...
4.9/5 Exceptional! (23 reviews)
YES
"Amazing. 10+ stars, if I could. Only drawback is it was kinda tough to locate first time, but it was all up from there. THANK YOU, Hosts, for a memorable weekend getaway! Will be back if possible! Ciaoooo!"

Reviewed on Apr 23, 2022

Carriage House Hideaway in Middle of Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Chestertown, MD
Stay at this family-friendly vacation home in Chestertown. Enjoy free WiFi, onsite parking, and a garden. Our guests praise the comfy beds in our reviews. Popular ...
4.8/5 Exceptional! (34 reviews)
Great place
"This house is amazing, comfy, great view"

Reviewed on Oct 4, 2021

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
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 in Chestertown