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

Search Motels in Chestertown from CA $86

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Check prices for these dates

Next weekend
Sep 11 - Sep 13
In two weeks
Sep 18 - Sep 20
In one month
Oct 2 - Oct 4
In two months
Oct 30 - Nov 1

Our top choices for Chestertown motels

A row of motel rooms with stone walls and red doors.

1. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (180 reviews)
"surprisingly, this place was nice, room was semi-clean. Man at counter was nice even though his tone seemed rough but overall he was just a nice man. Bed sheets were still dirty. the bed my daughter slept on had a small blood stain on it. There was little black stuff all over the bed but besides that it was quiet and thats what i needed"
United States
Vanesa
The price is CA $88
CA $98 total
includes taxes & fees
Sep 7 - Sep 8
Driftwood Inn
A spacious interior with a staircase, a chandelier, a stone wall, and a Day's Inn snack bar.

2. Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (1,002 reviews)
"It was a restful stay."
United States
Luis
The price is CA $97
CA $109 total
includes taxes & fees
Sep 13 - Sep 14
Days Inn by Wyndham Aberdeen
A Super 8 hotel with a prominent sign, a large building with multiple windows, and a well-lit entrance.

3. Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (900 reviews)
"Good"
United States
Piyush
The price is CA $77
CA $86 total
includes taxes & fees
Sep 27 - Sep 28
Super 8 by Wyndham Aberdeen MD

4. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (520 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 CA $113
CA $129 total
includes taxes & fees
Sep 27 - Sep 28
Village Inn Annapolis MD
A multi-story motel with a brick facade, multiple windows, and a parking lot.

5. Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (505 reviews)
"Enjoyed my stay"
United States
Brittany
The price is CA $110
CA $127 total
includes taxes & fees
Sep 7 - Sep 8
Super 8 by Wyndham Baltimore/Essex Area
A restaurant with wooden beams, stone walls, and a fireplace. Tables are set with red tablecloths and chairs.

6. 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
Sep 25 - Sep 26
White Marsh Motel
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
"Fantastic location. Clean room with comfortable beds and powerful AC. Liked the history of the building. We were able to consistently get parking on the street near the hotel, which was great. The only real con was that we discovered upon reaching our room that we didn't have an exterior window--our two "windows" looked over the covered event area, which had pretty lights but was nonetheless an interior hallway, so no outside view. There were also a couple hiccups with the bathroom, one being that the glass shelf was falling down, and the other being that we were consistently given two towels even though we had four people on the reservation. But overall we were happy with our stay and appreciated being in a historic building in such a great location."
Robyn 3-night trip
Posted 1 hour ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Motels information

Number of reviews
1,585
Accommodation
11 Motels
Lowest Price
CA $86
Highest Price
CA $129

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 45 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. Room amenities like free WiFi are included, along with freebies like breakfast, parking, and a cruise ship terminal shuttle. 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, Historical Society of Kent County Maryland, 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.

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