Search Motels in Chestertown from CA $88

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jun 12 - Jun 14
In two weeks
Jun 19 - Jun 21
In one month
Jul 3 - Jul 5
In two months
Jul 31 - Aug 2

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 CA $88
CA $98 total
includes taxes & fees
Jun 5 - Jun 6
Driftwood Inn
Exterior

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (874 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 CA $79
CA $88 total
includes taxes & fees
Jun 11 - Jun 12
Super 8 by Wyndham Aberdeen 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 CA $100
CA $115 total
includes taxes & fees
Jul 1 - Jul 2
White Marsh Motel
Lobby

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (969 reviews)
"It's better than Red Roof but definitely spend the money for better if with the Family"
United States
Christopher
The price is CA $96
CA $107 total
includes taxes & fees
Jun 7 - Jun 8
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, (467 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 CA $120
CA $139 total
includes taxes & fees
Jun 9 - Jun 10
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Hampton Inn Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

10/10 Excellent
"The room 135 is needing a modern refresh. Otherwise I enjoyed the stay"
Carl 4-night trip
Posted 2 hours ago
Hampton Inn Baltimore/White Marsh

Find out more about Chestertown

Chestertown Motels information

Number of reviews
2,487
Accommodation
11 Motels
Lowest Price
CA $88
Highest Price
CA $139

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. Super 8 by Wyndham Baltimore/Essex Area: Enjoy the in-room free WiFi, and freebies including breakfast, 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 like breakfast, WiFi, and 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 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.

Explore a world of travel with Expedia