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Check prices for these dates

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

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 HK$498
HK$553 total
includes taxes & fees
4 Sept - 5 Sept
Driftwood Inn
A Super 8 hotel with a prominent sign, a large building with multiple windows, and a well-lit entrance.

2. Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (899 reviews)
"Good"
United States
Piyush
The price is HK$440
HK$493 total
includes taxes & fees
9 Sept - 10 Sept
Super 8 by Wyndham Aberdeen MD
A spacious interior with a staircase, a chandelier, a stone wall, and a Day's Inn snack bar.

3. Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (1,000 reviews)
"It was a restful stay."
United States
Luis
The price is HK$514
HK$576 total
includes taxes & fees
6 Sept - 7 Sept
Days Inn by Wyndham Aberdeen

4. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (519 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 HK$651
HK$742 total
includes taxes & fees
15 Sept - 16 Sept
Village Inn Annapolis MD
A restaurant with wooden beams, stone walls, and a fireplace. Tables are set with red tablecloths and chairs.

5. 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 HK$565
HK$652 total
includes taxes & fees
25 Sept - 26 Sept
White Marsh Motel
A multi-story motel with a brick facade, multiple windows, and a parking lot.

6. 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 HK$619
HK$715 total
includes taxes & fees
3 Sept - 4 Sept
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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good
"Ok"
Joseph 5-night trip
Posted 11 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Find out more about Chestertown

Chestertown Motels information

Number of reviews
1,584
Accommodation
10 Motels
Lowest Price
HK$493
Highest Price
HK$742

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 44 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: If driving, you'll be within 21 minutes of Chesapeake Bay. Enjoy access to the 24-hour front desk, and freebies including WiFi and self-parking. Days Inn by Wyndham Aberdeen: A seasonal outdoor pool along with freebies such as breakfast, WiFi and self-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 self-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 such as free Wi-Fi are included, along with freebies such as breakfast, self-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 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: Chestertown Historic District, Historical Society of Kent County Maryland 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.

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