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Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Motels in Chestertown

In-room safe, desk, soundproofing, iron/ironing board
Days Inn by Wyndham Aberdeen
Days Inn by Wyndham Aberdeen
2.0 star property
7.0 out of 10, Good, (898)
"Was a great place to stay for 8 hours"
United States
David
The price is AED 268
AED 300 total
includes taxes & fees
10 Nov - 11 Nov
Days Inn by Wyndham Aberdeen
Exterior
Super 8 by Wyndham Aberdeen MD
Super 8 by Wyndham Aberdeen MD
2.0 star property
7.0 out of 10, Good, (852)
"Parking was easy. Bed was super comfy. "
United States
Martha J.
The price is AED 215
AED 241 total
includes taxes & fees
16 Nov - 17 Nov
Super 8 by Wyndham Aberdeen MD
Marina
Mariners Motel
Mariners Motel
2.0 star property
9.4 out of 10, Exceptional, (90)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
United States
Tim
The price is AED 528
AED 586 total
includes taxes & fees
2 Nov - 3 Nov
Mariners Motel
Restaurant
White Marsh Motel
White Marsh Motel
2.0 star property
6.6 out of 10, (27)
"Starting with the checking service was friendly and accommodating "
United States
William
White Marsh Motel
Exterior
Super 8 by Wyndham Baltimore/Essex Area
Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
5.4 out of 10, (398)
"Just a nice quiet cool place clean rooms and the bed is away from the door lol"
United States
Jamelle
The price is AED 309
AED 356 total
includes taxes & fees
26 Oct - 27 Oct
Super 8 by Wyndham Baltimore/Essex Area
Reception
Village Inn Annapolis MD
Village Inn Annapolis MD
2.0 star property
6.2 out of 10, (504)
"The room was very nice, clean and quiet. Great location"
United States
William
The price is AED 305
AED 348 total
includes taxes & fees
2 Nov - 3 Nov
Village Inn Annapolis MD
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

Garner Hotel Glen Burnie BWI Airport Area by IHG

Garner Hotel Glen Burnie BWI Airport Area by IHG

10/10 Excellent
"Perfect stay! from the light lavendar fresh painted walls to the fluffy white bed pillows, it was an excellent choice of hotels to stay. The breakfast room has plenty of room to enjoy the morning freshly grinded and brewed coffee and the variety of breakfast items! Loved the whole hotel experience!"
Dawn 1-night trip
Posted 2 days ago
Garner Hotel Glen Burnie BWI Airport Area by IHG

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 38 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. Days Inn by Wyndham Aberdeen: A seasonal outdoor pool along with freebies like breakfast, WiFi, and 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 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. Room amenities like free WiFi are included, along with freebies like breakfast, parking, and a cruise ship terminal shuttle. 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 parking.
What can I do in Chestertown?
These are some of the parks and outdoorsy places: Chesapeake Bay, Chestertown Dog Park, and Urieville Park. You'll find these family-friendly attractions in the area: Crumpton Auction and Hazel Miner Monument. 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.