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Check prices for these dates

Next weekend
18 Sep - 20 Sep
In two weeks
25 Sep - 27 Sep
In one month
9 Oct - 11 Oct
In two months
6 Nov - 8 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, (181 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is ฿2,099
฿2,330 total
includes taxes & fees
14 Sept - 15 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, (902 reviews)
"Good"
United States
Piyush
The price is ฿1,854
฿2,077 total
includes taxes & fees
20 Sept - 21 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, (1,002 reviews)
"It was a restful stay."
United States
Luis
The price is ฿2,166
฿2,426 total
includes taxes & fees
20 Sept - 21 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, (522 reviews)
"very clean room. All the basic items you need from a budget motel. I admit on the outside the motel looks a bit rough, but inside the rooms where it really matters, it was clean, well organized, and comfortable. I would stay here again, if I was looking for a cheap accommodation in the Annapolis area. Despite being right next to a busy state highway, it was very quiet and conveniently located to a couple of local restaurants and a convenience store."
United States
Keith
The price is ฿2,743
฿3,127 total
includes taxes & fees
14 Sept - 15 Sept
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, (507 reviews)
"Enjoyed my stay"
United States
Brittany
The price is ฿2,908
฿3,359 total
includes taxes & fees
17 Sept - 18 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

Historic Inns of Annapolis

Historic Inns of Annapolis

8/10 Good
"Property was a historical renovation which is very well done. Best part was location. A bit pricey and we didn’t need or use the complimentary bottle of wine. Bottled water would have been preferred. Staff and housekeeping was great. Coffee was available, but no food service for breakfast."
Charles 2-night trip
Posted 16 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Motels information

Number of reviews
2,607
Accommodation
10 Motels
Lowest Price
฿2,077
Highest Price
฿3,359

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 45 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: 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 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.