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

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Check prices for these dates

Next weekend
3 Jul - 5 Jul
In two weeks
10 Jul - 12 Jul
In one month
24 Jul - 26 Jul
In two months
21 Aug - 23 Aug

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, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is NZ$125
includes taxes & fees
12 July - 13 July
Driftwood Inn
Fridge, microwave

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (508 reviews)
"The room was very nice, clean and quiet. Great location"
United States
William
The price is NZ$168
includes taxes & fees
12 July - 13 July
Village Inn Annapolis MD
Restaurant

White Marsh Motel

White Marsh Motel
2.0 star property
White Marsh
6.6 out of 10, (27 reviews)
"Starting with the checking service was friendly and accommodating "
United States
William
The price is NZ$147
includes taxes & fees
13 July - 14 July
White Marsh Motel
Exterior

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (883 reviews)
"Room was dirty, housekeeping ignored the do not disturb sign and barged in when trying to get dressed and would not leave. Roaches in room."
United States
Farrah
The price is NZ$118
includes taxes & fees
28 June - 29 June
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, (986 reviews)
"It's better than Red Roof but definitely spend the money for better if with the Family"
United States
Christopher
The price is NZ$132
includes taxes & fees
30 June - 1 July
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, (479 reviews)
"SPOTLESSLY CLEAN ROOM BIG WORKING TV, EASY CHECK-IN & CHECK-OUT Premises Could Be Better Kept A bit Noisy"
United States
Jared
The price is NZ$184
includes taxes & fees
12 July - 13 July
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

10/10 Excellent
"The Johnson House was very well maintained, was welcoming with a historic flair. The access to downtown was easy, and felt very safe."
Cassady 4-night trip
Posted 4 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Motels information

Number of reviews
2,525
Accommodation
10 Motels
Lowest Price
NZ$118
Highest Price
NZ$184

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 44 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. 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. White Marsh Motel: 22 mi (35.3 km) from the heart of Chestertown. Enjoy access to the 24-hour front desk, 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: 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.