Chestertown, MD

Travel Guide

An aerial view of a town with a river, buildings, and surrounding greenery.
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.
A riverside residential area with houses, docks, and a clear blue sky.
A riverside town with red brick buildings, a dock, and autumn foliage.
A calm lake with a sailboat, trees, and a house on the shore.
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$3,548 per night from Nov 11 to Nov 12
NT$3,548
NT$4,056 total
Nov 11 - Nov 12
includes taxes & fees
Book a stay at this 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! (129 reviews)
"Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area."

Reviewed on 2026/11/8

The Lodge at Great Oak Landing
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2 out of 5
160 Scheeler Rd Chestertown MD
The price is NT$2,363 per night from Nov 17 to Nov 18
NT$2,363
NT$2,623 total
Nov 17 - Nov 18
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 ...
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$3,171 per night from Dec 6 to Dec 7
NT$3,171
NT$3,520 total
Dec 6 - Dec 7
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 ...
8.6/10 Excellent! (1,000 reviews)
"Convenient location, friendly staff, clean"

Reviewed on 2026/11/8

Comfort 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.
Hudson house

Hudson house

4 out of 5
3037 Hudson St Baltimore MD
Stay at this vacation home in Baltimore. Enjoy free WiFi, free parking, and daily housekeeping. Popular attractions Baltimore Inner Harbor Marina and M&T Bank ...
7.6/10 Good! (5 reviews)
"Tried messaging multiple times prior to check in to confirm check in process and possibility of checking in early, no response. Finally called upon arrival, was told they had to confirm my reservation and would call back, after waiting an hour, called 3x no answer, eventually spoke to someone else ..."

Reviewed on 2026/9/3

Hudson house
Bohemia Manor Farm

Bohemia Manor Farm

3.5 out of 5
237 Bohemia Manor Farm Ln Chesapeake City MD
Book a stay at this beach vacation home in Chesapeake City. Enjoy free WiFi, free parking, and a private beach. Popular attractions Bohemia Anchorage and Hack's ...
Bohemia Manor Farm
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.

Stay near popular Chestertown attractions

Cities near Chestertown