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

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Check prices for these dates

Next weekend
Aug 14 - Aug 16
In two weeks
Aug 21 - Aug 23
In one month
Sep 4 - Sep 6
In two months
Oct 2 - Oct 4

Our top choices for Chestertown motels

Front of property - evening/night

1. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (180 reviews)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is ￥10,018
￥11,121 total
includes taxes & fees
Aug 10 - Aug 11
Driftwood Inn
Exterior

2. Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (892 reviews)
"Good"
United States
Piyush
The price is ￥8,852
￥9,914 total
includes taxes & fees
Aug 16 - Aug 17
Super 8 by Wyndham Aberdeen MD
Lobby

3. Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (1,008 reviews)
"Brandi—she is the best person I've ever met; the vibe she radiates is incredible."
United States
Mariela
The price is ￥10,364
￥11,608 total
includes taxes & fees
Aug 31 - Sep 1
Days Inn by Wyndham Aberdeen
Exterior

4. Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (496 reviews)
"Enjoyed my stay"
United States
Brittany
The price is ￥13,410
￥15,489 total
includes taxes & fees
Aug 10 - Aug 11
Super 8 by Wyndham Baltimore/Essex Area
Fridge, microwave

5. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (516 reviews)
"Always clean staff friendly professional used to pretty much live here years ago always worked with me treated me right.Highly recommend 👌 👍"
United States
Stephen
The price is ￥13,094
￥14,927 total
includes taxes & fees
Aug 10 - Aug 11
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

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"For tall(6'2") men bathroom amenities were a tight fit. Decor very nice."
Jacob 1-night trip
Posted 6 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Motels information

Number of reviews
1,072
Accommodation
10 Motels
Lowest Price
￥9,914
Highest Price
￥15,489

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 43 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: If driving, you'll be within 21 minutes of Chesapeake Bay. 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. A business center along with freebies like WiFi, parking, and a cruise ship terminal shuttle are available during your stay. 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: 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 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.