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Check prices for these dates

Next weekend
17 Apr - 19 Apr
In two weeks
24 Apr - 26 Apr
In one month
8 May - 10 May
In two months
5 Jun - 7 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 ₹5,905
₹6,555 total
includes taxes & fees
1 May - 2 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, (867 reviews)
"Breakfast could be better. "
United States
Joseph V
The price is ₹5,296
₹5,931 total
includes taxes & fees
21 Apr - 22 Apr
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, (943 reviews)
"Very good option, friendly staff and good price "
United States
Jose
The price is ₹6,025
₹6,748 total
includes taxes & fees
12 Apr - 13 Apr
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, (444 reviews)
"Staff was very rude when trying to get a room "
United States
michael
The price is ₹5,486
₹6,336 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

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

10/10 Excellent
"The lake was a big plus."
Ruth 2-night trip
Posted 2 hours ago
Hyatt Place Kent Narrows & Marina

Find out more about Chestertown

Chestertown Motels information

Number of reviews
1,562
Accommodation
11 Motels
Lowest Price
₹5,931
Highest Price
₹6,748

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 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. Super 8 by Wyndham Baltimore/Essex Area: Room amenities such as free Wi-Fi are included, along with freebies such as breakfast, self-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 self-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 such as breakfast, WiFi and self-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 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.