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

Find a Great Motel Chestertown

  • 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 prices for these dates

Next weekend
7 Aug - 9 Aug
In two weeks
14 Aug - 16 Aug
In one month
28 Aug - 30 Aug
In two months
25 Sept - 27 Sept

Our top choices for Chestertown motels

Front of property – evening/night

1. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (178 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is AU$100
includes taxes & fees
3 Aug - 4 Aug
Driftwood Inn
Exterior

2. Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (891 reviews)
"Good"
United States
Piyush
The price is AU$79
includes taxes & fees
1 Sept - 2 Sept
Super 8 by Wyndham Aberdeen MD
Lobby

3. Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (1,002 reviews)
"Brandi—she is the best person I've ever met; the vibe she radiates is incredible."
United States
Mariela
The price is AU$98
includes taxes & fees
1 Sept - 2 Sept
Days Inn by Wyndham Aberdeen
Fridge, microwave

4. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (514 reviews)
"Always clean staff friendly professional used to pretty much live here years ago always worked with me treated me right.Highly recommend 👌 👍"
United States
Stephen
The price is AU$135
includes taxes & fees
3 Aug - 4 Aug
Village Inn Annapolis MD
Exterior

5. Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (494 reviews)
"Enjoyed my stay"
United States
Brittany
The price is AU$140
includes taxes & fees
3 Aug - 4 Aug
Super 8 by Wyndham Baltimore/Essex Area
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Wonderful stay! Excellent location on the water. Had a room with a balcony. Staff and restaurants were all very nice."
Stacey 1-night trip
Posted 4 hours ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about Chestertown

Chestertown Motels information

Number of reviews
1,008
Accommodation
10 Motels
Lowest Price
AU$79
Highest Price
AU$140

Frequently asked questions

What can I expect from a motel trip to Chestertown?
If you can't find a motel in Chestertown, consider some of the motels we suggest around the area or let us help you find something similar from over 43 hotels and other lodging options. Just use our search tools to filter by nightly room rate or cost-saving amenities such as free breakfast and free airport transport.
What's it like to stay in a motel?
At most motels, you're likely to find a free parking spot and an outdoor pool. When you stay at a motel, you'll often have access to your room from an outside corridor overlooking the car park. Motels began in the 1920s as a place to stay for the weary traveller driving along America's major roadways.
What are the best motels in Chestertown?
Here are some of our customers' top motels to book in the larger area. Driftwood Inn: If driving, you'll be within 21 minutes of Chesapeake Bay. Enjoy access to the 24-hour front desk, and freebies including WiFi and self-parking. Days Inn by Wyndham Aberdeen: A seasonal outdoor pool along with freebies such as breakfast, WiFi and self-parking are available during your stay. Central Chestertown is 21.8 mi (35.1 km) away. Village Inn Annapolis MD: Enjoy access to the laundry facilities, and freebies including WiFi and self-parking. Located 25.6 mi (41.1 km) from the heart of Chestertown. Super 8 by Wyndham Baltimore/Essex Area: Central Chestertown is 21.8 mi (35 km) away. A business centre along with freebies such as WiFi, self-parking and a cruise ship terminal shuttle are available during your stay. Super 8 by Wyndham Aberdeen MD: 21.8 mi (35.1 km) from the heart of Chestertown. Enjoy access to the 24-hour front desk, and freebies including breakfast, WiFi and self-parking.
What can I do in Chestertown?
These are some of the parks and outdoorsy places: Northern Chesapeake Bay, Chesapeake Bay and Chestertown Dog Park. During your trip, here are some other places to visit: Chestertown Historic District, Rolphs Wharf Marina and Historical Society of Kent County Maryland.
What's the seasonal weather like in Chestertown?
Weather can make or break a road trip, so we've gathered some data about year-round temperatures in Chestertown to help you plan yours. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What are my options for getting around Chestertown while staying in a motel?
We've gathered some information about getting around Chestertown to help you navigate your stay: Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) away from the city centre. Otherwise, you can search for flights to Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.