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Check prices for these dates

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

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 ￥10,034
￥11,138 total
includes taxes & fees
Nov 13 - Nov 14
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
7.2 out of 10, Good, (1,003 reviews)
"The value for price was exceptional. Friendly and helpful staff."
United States
Daniel
The price is ￥10,958
￥12,274 total
includes taxes & fees
Dec 6 - Dec 7
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, (916 reviews)
"I've stayed here a lot it has been a pleasant experience..."
United States
Richard
The price is ￥8,596
￥9,626 total
includes taxes & fees
Nov 17 - Nov 18
Super 8 by Wyndham Aberdeen MD
A restaurant with wooden beams, stone walls, and a fireplace. Tables are set with red tablecloths and chairs.

4. 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 ￥11,377
￥13,140 total
includes taxes & fees
Nov 23 - Nov 24
White Marsh Motel
A hotel room with a large bed, two bedside tables with lamps, a headboard with a cityscape picture, and a wooden parquet floor.

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, (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 ￥13,431
￥15,513 total
includes taxes & fees
Nov 11 - Nov 12
Super 8 by Wyndham Baltimore/Essex Area
Private kitchen

6. Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (535 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 ￥13,115
￥14,951 total
includes taxes & fees
Nov 12 - Nov 13
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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Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Great hotel"
Tyrese 1-night trip
Posted 10 hours ago
Pendry Baltimore

Find out more about Chestertown

Chestertown Motels information

Number of reviews
3,162
Accommodation
10 Motels
Lowest Price
￥9,626
Highest Price
￥15,513

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. 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. 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 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 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.