Find Deals on
Inns in Chestertown

A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

Check Last Minute Chestertown Hotel Deals

Tonight Nov 12 - Nov 13 This weekend Nov 13 - Nov 15 Next weekend Nov 20 - Nov 22

You choose what matters — star rating, location, amenities.

We pick the perfect hotel, packed with all your must-haves.

Your hotel is revealed right after booking!

Cheap Inns in Chestertown

Historic Waterfront Kent Manor Inn

500 Kent Manor Dr Stevensville MD

Stay at this inn in Stevensville. Popular attractions Northern Chesapeake Bay and Paul Reed Smith Guitars are located nearby.

Get rates

See all 1,099 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.

Top Trending Hotels in Chestertown

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

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 Nov 8, 2026

Get rates

The Lodge at Great Oak Landing

22170 Great Oak Landing Rd Chestertown MD

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 Nov 8, 2026

Get rates

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

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 ...

Get rates

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.