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Search Motels in Chestertown

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Compare 12 Motels in Chestertown with updated reviews, rates, and availability.

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (748)
"It was fine and served our needs."
The price is SAR 366
SAR 406 total
includes taxes & fees
1 Apr - 2 Apr
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (335)
"This property was def. Off season. It was very low key, the room was big and clean, hotel understaffed but I think it was just the time of year. Overall would for sure stay here again.Big value for the cost"
The price is SAR 209
SAR 232 total
includes taxes & fees
10 Mar - 11 Mar
Red Roof Inn & Suites Chestertown

Driftwood Inn

2.0 star property
5.0 out of 10, (167)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is SAR 238
SAR 264 total
includes taxes & fees
10 Mar - 11 Mar
Driftwood Inn

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (46)
"Generally okay, Clean but property could use some upgrade"
The price is SAR 405
SAR 450 total
includes taxes & fees
18 Mar - 19 Mar
The Lodge at Great Oak Landing
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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Other property types in Chestertown

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (79)
"This property is located in a excellent neighborhood overlooking a golf course and a short distance to the Chester river. The room was immaculate and ideal for all ages, especially Senior citizens. We booked this room for our 67th wedding anniversary in the first week in February with unfavorable weather, but the room was very cozy. We will defiently return later this year."
The price is SAR 368
SAR 592 total
includes taxes & fees
5 Mar - 6 Mar
First Floor Studio Apartment in Historic Chestertown

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (22)
"Decided to try something different, and luckily found the Dockside Doghouse. Very comfortable, incredibly relaxing."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (256)
"Such a hidden gem of a spot! Pictures were exactly like the house and the owners were super responsive!"
Captivating Chesapeake experience
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.

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 41 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: 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 Aberdeen MD: Enjoy access to the 24-hour front desk, and freebies including breakfast, WiFi, and parking. Located 21.8 mi (35.1 km) from the heart of Chestertown. Super 8 by Wyndham Baltimore/Essex Area: Central Chestertown is 21.8 mi (35 km) away. A business center along with freebies like WiFi, parking, and a cruise ship terminal shuttle are available during your stay. Village Inn: 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: Kings Town Park, Rolling Road Park, and Chestertown Dog Park. You’ll find these family-friendly attractions in the area: Crumpton Auction and Hazel Miner Monument. During your trip, here are some other places to visit: Rolphs Wharf Marina, 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 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.