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Find Cheap Hotels in Chestertown, MD

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Compare Chestertown Cheap Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Red Roof Inn & Suites Chestertown
Exterior

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (322)
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. You have to go out for breakfast. Excuse was not since Covid. That adds another $20 per couple for breakfast to the room price."
The price is AED 251
AED 279 total
includes taxes & fees
7 Jan - 8 January 2025
Red Roof Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Exterior

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (736)
"Front desk staff was welcoming and friendly. We had a suite so I am guessing it was a bit larger than a regular room but it was really wonderful to have the extra space. The room was clean and the breakfast was decent (the coffee was good for hotel coffee). Would certainly stay here again when I am in the area. "
The price is AED 387
AED 430 total
includes taxes & fees
12 Jan - 13 January 2025
Comfort Inn & Suites Chestertown
Driftwood Inn
Front of property - evening/night

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 AED 233
AED 259 total
includes taxes & fees
7 Jan - 8 January 2025
Driftwood Inn
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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Frequently asked questions

What is Chestertown like for travelers on a budget?
Chestertown has a variety of cheap accommodations and places to visit, making it a great getaway spot for budget travelers. You can find ways to save money while getting to know this destination, which is home to attractions like Rolphs Wharf Marina, Historical Society of Kent County Maryland, and Garfield Center for the Arts at the Prince Theater.
When is the best time for a budget trip to Chestertown?
Weather will likely play an important role when you plan your trip to Chestertown, and keep in mind that cheaper options are usually available when the weather isn’t as good. 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 is there to see and do in Chestertown?
You don’t have to spend a fortune to find things to see and do in Chestertown. You can budget for the local attractions that interest you most, and then plan some activities that cost little or nothing at all. If you’re eager to get outdoors, you can enjoy the natural setting at Wilmer Park, Rolling Road Park, or Kings Town Park.
How can I get to Chestertown and get around on a budget?
Scoping out the transportation options in Chestertown is a smart way to keep your trip affordable. The nearest airport is Baltimore, MD (MTN-Martin State), 20.3 mi (32.7 km) away. However, if that doesn’t suit your budget, the next closest is 28.2 mi (45.3 km) away: Easton, MD (ESN-Easton - Newnam). Chestertown might not have very many public transportation choices so a car rental could be an economical alternative to see the area.