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Check prices for these dates

Next weekend
8 May - 10 May
In two weeks
15 May - 17 May
In one month
29 May - 31 May
In two months
26 Jun - 28 Jun

Our top choices for Chestertown motels

Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is 1.672.844 ₫
1.856.989 ₫ total
includes taxes & fees
23 May - 24 May
Driftwood Inn
Exterior

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
7.0 out of 10, Good, (868 reviews)
"Skipped the breakfast but there were several options. Friendly and helpful staff. Bathroom door didn’t shut properly and room table/wall surfaces could have used a little more cleaning focus. Beds were clean and nice. Bodywash in shower was empty. Room smelled VERY strong of Hawaiian air freshener. Parking was easy"
United States
Jordyn
The price is 1.478.162 ₫
1.655.542 ₫ total
includes taxes & fees
4 May - 5 May
Super 8 by Wyndham Aberdeen MD
Lobby

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (950 reviews)
"Very good option, friendly staff and good price "
United States
Jose
The price is 1.712.360 ₫
1.917.843 ₫ total
includes taxes & fees
3 May - 4 May
Days Inn by Wyndham Aberdeen
Exterior

Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (449 reviews)
"Staff was very rude when trying to get a room "
United States
michael
The price is 1.554.296 ₫
1.795.344 ₫ total
includes taxes & fees
4 May - 5 May
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

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Great location. Very cozy and clean."
Angela 1-night trip
Posted 2 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Motels information

Number of reviews
2,442
Accommodation
11 Motels
Lowest Price
1.655.542 ₫
Highest Price
1.917.843 ₫

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 42 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 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: Rolphs Wharf Marina, Historical Society of Kent County Maryland 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.