Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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Check prices for these dates

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16

Our top choices for Chestertown motels

Front of property - evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is NT$2,006
NT$2,226 total
includes taxes & fees
Jun 22 - Jun 23
Driftwood Inn
Restaurant

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 NT$2,274
NT$2,627 total
includes taxes & fees
Jul 1 - Jul 2
White Marsh Motel
Exterior

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (881 reviews)
"Room was dirty, housekeeping ignored the do not disturb sign and barged in when trying to get dressed and would not leave. Roaches in room."
United States
Farrah
The price is NT$1,876
NT$2,101 total
includes taxes & fees
Jun 22 - Jun 23
Super 8 by Wyndham Aberdeen MD
Fridge, microwave

Village Inn Annapolis MD

Village Inn Annapolis MD
2.0 star property
Annapolis
6.2 out of 10, (508 reviews)
"The room was very nice, clean and quiet. Great location"
United States
William
The price is NT$2,622
NT$2,989 total
includes taxes & fees
Jun 22 - Jun 23
Village Inn Annapolis MD
Lobby

Days Inn by Wyndham Aberdeen

Days Inn by Wyndham Aberdeen
2.0 star property
Aberdeen
7.0 out of 10, Good, (979 reviews)
"It's better than Red Roof but definitely spend the money for better if with the Family"
United States
Christopher
The price is NT$2,104
NT$2,356 total
includes taxes & fees
Jun 30 - Jul 1
Days Inn by Wyndham Aberdeen
Exterior

Super 8 by Wyndham Baltimore/Essex Area

Super 8 by Wyndham Baltimore/Essex Area
2.0 star property
Essex
5.6 out of 10, (474 reviews)
"SPOTLESSLY CLEAN ROOM BIG WORKING TV, EASY CHECK-IN & CHECK-OUT Premises Could Be Better Kept A bit Noisy"
United States
Jared
The price is NT$2,969
NT$3,429 total
includes taxes & fees
Jun 23 - Jun 24
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
"We stayed here a little over a year ago at one of the sister inns associated with this property and had such a positive experience that we decided to return. Overall, the hotel is reasonably priced, clean, and conveniently located close to everything, which made our stay enjoyable. While the property itself is a bit outdated, it has a charming and quaint feel that we appreciated. The front desk staff were friendly, welcoming, and helpful throughout our stay. The only disappointing part of our experience was the valet service. We arrived early and dropped off our bags, at which point our car was taken by valet. Unfortunately, there was no clear communication that valet was a paid service, and during our previous stay it had been complimentary. When we returned at check-in time, we were told the valet would drive us to our room with our bags, but when the cart was unavailable, we were simply told “sorry” and not offered the option to wait for assistance. Thankfully, we only had small bags and were able to walk. The following morning at checkout, we were surprised to find the valet charge was just under $65. For that price, we would have preferred the option to park ourselves, especially given the lack of service the day before. Transparency about valet pricing upfront would have made a big difference and allowed us to make an informed decision. Overall, the hotel itself was pleasant, but the valet experience left us disappointed."
Nicole 1-night trip
Posted less than an hour ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Motels information

Number of reviews
2,511
Accommodation
10 Motels
Lowest Price
NT$2,101
Highest Price
NT$3,429

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 42 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. Super 8 by Wyndham Aberdeen MD: Central Chestertown is 21.8 mi (35.1 km) away. A 24-hour front desk along with freebies like breakfast, WiFi, and parking are available during your stay. Village Inn Annapolis MD: 25.6 mi (41.1 km) from the heart of Chestertown. Enjoy access to the laundry facilities, and freebies including 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, Rolphs Wharf Marina, and Historical Society of Kent County Maryland.
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.