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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

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
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is S$91
includes taxes & fees
16 Nov - 17 Nov
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, (1,003 reviews)
"The value for price was exceptional. Friendly and helpful staff."
United States
Daniel
The price is S$99
includes taxes & fees
29 Nov - 30 Nov
Days Inn by Wyndham Aberdeen
A hotel room with a large bed, a desk, a chair, a TV, and a window with curtains.

3. Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (918 reviews)
"I've stayed here a lot it has been a pleasant experience..."
United States
Richard
The price is S$78
includes taxes & fees
22 Nov - 23 Nov
Super 8 by Wyndham Aberdeen MD
A hotel room with a large bed, two bedside tables with lamps, a headboard with a cityscape picture, and a wooden parquet floor.

4. Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (525 reviews)
"This is the worst hotel to stay at—it’s dirty and has mice, cockroaches, and bed bugs. Try to avoid this hotel; it should be reported to the health department."
United States
Iven Jose
The price is S$128
includes taxes & fees
16 Nov - 17 Nov
Super 8 by Wyndham Baltimore/Essex Area
Private kitchen

5. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (536 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 S$122
includes taxes & fees
16 Nov - 17 Nov
Village Inn Annapolis MD
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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Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

See all hotels in Chestertown
A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

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. Super 8 by Wyndham Baltimore/Essex Area: Enjoy the in-room free WiFi, and freebies including breakfast, self-parking and a cruise ship terminal shuttle. Located 21.8 mi (35 km) from the heart of Chestertown. Village Inn Annapolis MD : Central Chestertown is 25.6 mi (41.1 km) away. Free WiFi, free parking and laundry facilities are available during your stay. 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.