Search Motels in Chestertown

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Check prices for these dates

Next weekend
19 Dec - 21 Dec
In two weeks
26 Dec - 28 Dec
In one month
9 Jan - 11 Jan
In two months
6 Feb - 8 Feb

Our top choices for Chestertown motels

Front of property - evening/night
Driftwood Inn

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is AED 233
AED 259 total
includes taxes & fees
24 Dec - 25 Dec
Driftwood Inn
Exterior
Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
7.0 out of 10, Good, (859)
"Nice and clean. Staff was friendly. I had no problems whatsoever, and I would stay here again."
United States
Shelly
The price is AED 194
AED 217 total
includes taxes & fees
21 Dec - 22 Dec
Super 8 by Wyndham Aberdeen MD
Lobby
Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (914)
"Stayed here numerous time, friendly staff, easy check in, quick breakfast, clean room. "
United States
Brett
The price is AED 227
AED 254 total
includes taxes & fees
21 Dec - 22 Dec
Days Inn by Wyndham Aberdeen
Restaurant
White Marsh Motel

White Marsh Motel

White Marsh Motel
2.0 star property
White Marsh
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

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.4 out of 10, (412)
"The hotel was great the staff was great very clean "
United States
Sean
The price is AED 257
AED 297 total
includes taxes & fees
18 Dec - 19 Dec
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

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Really nice cozy room we had the terrace balcony would definitely stay again!"
Takema 1-night trip
Posted 2 days ago
Pendry Baltimore

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. Super 8 by Wyndham Aberdeen MD: Enjoy access to the 24-hour front desk, and freebies including breakfast, WiFi, and parking. Located 21.8 mi (35.1 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. 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. 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, Chestertown Historic District, and Rolphs Wharf Marina.
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.