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Check prices for these dates

Next weekend
27 Feb - 1 Mar
In two weeks
6 Mar - 8 Mar
In one month
20 Mar - 22 Mar
In two months
17 Apr - 19 Apr

Our top choices for Chestertown motels

Lobby

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (931 reviews)
"Clean rooms, great staff"
United States
Patricia
The price is S$87
includes taxes & fees
1 Mar - 2 Mar
Days Inn by Wyndham Aberdeen
In-room safe, desk, iron/ironing board, free WiFi

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (866 reviews)
"Horrible. Not clean. Smelly. Old"
United States
LaTarsha
The price is S$77
includes taxes & fees
1 Mar - 2 Mar
Super 8 by Wyndham Aberdeen MD
Desk, iron/ironing board, free cots/infant beds, free WiFi

Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (428 reviews)
"Mice and all kind of bugs had to buy blankets to sleep on from the people staying there looked like a halfway house very disappointed coming from Expedia I trust your company on all my business trips I will start checking the reviews. Sorry to say but that was a waist of had money."
United States
Emanuel
The price is S$106
includes taxes & fees
22 Feb - 23 Feb
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.
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Top Chestertown Hotel Reviews

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

10/10 Excellent
"The service team and all the staff were awesome!! No complaints from me at all "
Michelle 1-night trip
Posted 3 days ago
Fairfield Inn & Suites by Marriott Middletown

Find out more about Chestertown

Chestertown Motels information

Number of reviews
2,221
Accommodation
11 Motels
Lowest Price
S$77
Highest Price
S$106

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 40 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: 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. Super 8 by Wyndham Baltimore/Essex Area: Enjoy the in-room free WiFi, and freebies including breakfast, self-parking and a cruise ship terminal shuttle. Located 21.8 mi (35 km) from the heart of Chestertown. Super 8 by Wyndham Aberdeen MD: Central Chestertown is 21.8 mi (35.1 km) away. A 24-hour front desk along with freebies such as breakfast, WiFi and self-parking are available during your stay. Mariners Motel: 11 mi (17.7 km) from the heart of Chestertown. Enjoy access to the seasonal outdoor pool, and freebies including 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: Historical Society of Kent County Maryland, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater.
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.

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