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Check prices for these dates

Next weekend
Apr 3 - Apr 5
In two weeks
Apr 10 - Apr 12
In one month
Apr 24 - Apr 26
In two months
May 22 - May 24

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 ￥10,791
￥11,978 total
includes taxes & fees
Apr 9 - Apr 10
Driftwood Inn
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
7.0 out of 10, Good, (867 reviews)
"Breakfast could be better. "
United States
Joseph V
The price is ￥8,903
￥9,973 total
includes taxes & fees
Apr 2 - Apr 3
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, (938 reviews)
"Very good option, friendly staff and good price "
United States
Jose
The price is ￥9,855
￥11,039 total
includes taxes & fees
Mar 29 - Mar 30
Days Inn by Wyndham Aberdeen
Desk, iron/ironing board, free cribs/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, (439 reviews)
"Staff was very rude when trying to get a room "
United States
michael
The price is ￥11,743
￥13,563 total
includes taxes & fees
Mar 30 - Mar 31
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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Frindly staff. Slight noise but not bad. Rooms clean and comfortable. "
Matthew 1-night trip
Posted 13 hours ago
Comfort Inn & Suites Chestertown

Find out more about Chestertown

Chestertown Motels information

Number of reviews
1,552
Accommodation
11 Motels
Lowest Price
￥9,973
Highest Price
￥13,563

Frequently asked questions

What can I expect from a motel trip to Chestertown?
If you're having difficulty finding 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. Simply filter using our search tools by nightly room rate or cost-effective amenities such as free parking and free breakfast.
What's it like to stay in a motel?
At most motels, you're likely to find an outdoor pool and a free parking spot. When you stay at a motel, you'll often have access to your room from an outside corridor overlooking the parking lot. Motels began in the 1920s as a convenient place to stay for the weary traveler taking a road trip along America's major roadways.
What are the best motels in Chestertown?
Here you'll find some of our customers' favorite motels to choose from in the larger area. Driftwood Inn: Enjoy access to the 24-hour front desk, and freebies including WiFi and parking. Super 8 by Wyndham Baltimore/Essex Area: Room amenities like free WiFi are included, along with freebies like breakfast, parking, and a cruise ship terminal shuttle. Central Chestertown is 21.8 mi (35 km) away. Days Inn by Wyndham Aberdeen: Enjoy access to the seasonal outdoor pool, and freebies including breakfast, WiFi, and parking. Located 21.8 mi (35.1 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 like breakfast, WiFi, and parking are available during your stay. Village Inn Annapolis MD: 25.6 mi (41.1 km) from the heart of Chestertown. Enjoy access to the laundry facilities, and freebies including WiFi and 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 roadtrip, 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 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 are my options for getting around Chestertown when staying in a motel?
We've gathered some information about local transportation options in 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 heart of the city. Otherwise, look for flights into 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.