An aerial view of a town with a river, buildings, and surrounding greenery.

Find Beach Hotels in Chestertown, MD

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Beach Hotels

Next weekend
Nov 6 - Nov 8
In two weeks
Nov 13 - Nov 15

Our top choices for Chestertown beach hotels

A hotel lobby with a fireplace, seating area, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (997 reviews)
"Good hotel"
United States
Michael
The price is NT$3,201
NT$3,553 total
includes taxes & fees
Nov 29 - Nov 30
Comfort Inn & Suites Chestertown
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (511 reviews)
"Friendly staff, plenty of parking spaces,family friendly. The building is old but would do some renovation. Furniture needs replacement."
United States
Mary
The price is NT$2,343
NT$2,600 total
includes taxes & fees
Nov 12 - Nov 13
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

3. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is NT$2,066
NT$2,294 total
includes taxes & fees
Nov 4 - Nov 5
Driftwood Inn
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

4. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (124 reviews)
"Nice restairant and bar"
United States
Steve allen
The price is NT$3,515
NT$4,018 total
includes taxes & fees
Nov 5 - Nov 6
The Lodge at Great Oak Landing
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.
View all properties

Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

Frequently asked questions

What is Chestertown like for travelers who love the beach?
Known for its university life, Chestertown offers a lot for the traveler planning a getaway.
What's the best hotel for a beach vacation in Chestertown?
The Lodge at Great Oak Landing is a top lodge with 2 restaurants and a seasonal outdoor pool, and it's located near a private beach. Great Oak Manor is another good option to stay near the beach.
When's the best time for a beach vacation in Chestertown?
You can plan your beach trip with this snapshot of the seasons in Chestertown: The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
What is there to see and do around Chestertown?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. Beach lovers can head straight to Betterton Beach or Main Beach for some quality time by the water. Experience the area's university life, and make time for local attractions like Washington College and River Arts Chestertown. For more things to see and do, consider visiting Historical Society of Kent County Maryland or Chestertown Historic District.
What's the best way to get to my beach hotel in Chestertown?
Here's some information to help you get to and around your beach accommodation in Chestertown more easily: To get to Chestertown, book a flight to Baltimore, MD (MTN-Martin State), the closest major airport, which is located 20.3 mi (32.7 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.

Explore a world of travel with Expedia