An aerial view of a town with a river, buildings, and surrounding greenery.

Find Cheap Hotels in Chestertown, MD

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Check availability on Chestertown Cheap Hotels

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
No exact matches found, but these alternatives could be just right

Recommended hotels in Chestertown

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
NT$3,162
NT$3,509 total
includes taxes & fees
Nov 8 - Nov 9
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A living room with a fireplace, a television, and a stone accent wall.
A multi-story brick building with a covered entrance and a parking lot.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Kate
NT$2,333
NT$2,589 total
includes taxes & fees
Nov 1 - Nov 2
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.
A two-story building with a brick facade, large windows, and a sloped roof.
A living room with a wooden cabinet, a television, a sofa, and a dining table.

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
NT$2,057
NT$2,284 total
includes taxes & fees
Oct 18 - Oct 19
Driftwood Inn
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
A campfire in a stone fire pit by a lakeside at sunset.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

4. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Steve allen
NT$3,499
NT$4,001 total
includes taxes & fees
Oct 19 - Oct 20
The Lodge at Great Oak Landing
Two Adirondack chairs facing a calm body of water with a clear sky above.
A modern food court with a central island, various food stations, and a yogurt display.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
A reception desk with a modern design, a digital display, and a check-in counter.

5. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
NT$3,208
NT$3,561 total
includes taxes & fees
Nov 15 - Nov 16
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

6. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
Thomas
NT$2,763
NT$3,095 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Edgewood/Aberdeen-South
A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.
A hotel room with a sofa, a bed, a desk, and a lamp.
A wedding ceremony in front of a large, classical building with steps leading up to the entrance.
A vending machine with snacks and a drink dispenser.

7. Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A
Edgewood
United States
Jose
NT$1,998
NT$2,237 total
includes taxes & fees
Oct 26 - Oct 27
Quality Inn & Suites Bel Air I-95 Exit 77A
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.
An outdoor patio with brick walls, green chairs, and a fire pit.
A hotel room with two beds, a bathroom, and a seating area.
A hotel with a modern facade, a covered entrance, and a red car parked outside.

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
Rashawna
NT$3,470
NT$4,008 total
includes taxes & fees
Nov 5 - Nov 6
SpringHill Suites Baltimore White Marsh/Middle River
A hotel room with a sofa, armchairs, a TV, a bed, and a large window.
A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.
A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.
A spacious lobby with a staircase, a reception desk, and a dining area.

9. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
United States
Crystal
NT$2,742
NT$3,043 total
includes taxes & fees
Nov 15 - Nov 16
Quality Inn Grasonville near Kent Island
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.
A gym with treadmills, elliptical machines, and a weight machine.

10. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
United States
Vanessa
NT$2,887
NT$3,233 total
includes taxes & fees
Nov 1 - Nov 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
View all properties

Top Chestertown Hotel Reviews

Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

8/10 Good
"Our stay was quite un eventful and very restful with the following exception; I had checked the wrong date on the arrival and called Expedia to correct it which they said they would do, then beyond that my brother in law passed away and we had to leave a day early, which the hotel was very understanding and only charged for the nights we stayed. BUT Expedia has not refunded any of the excessive charges for either of the two nights involved. They sent a letter saying the hotel would not accept refunding the two nights, which is completely not true as I have a copy of the bill from the hotel and it only covers the two nights we actually spent. At this time I can never trust Expedia again to book anything!"
Steve 3-night trip
Posted 5 days ago
Country Inn & Suites by Radisson, Baltimore North, MD

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 Historical Society of Kent County Maryland, Chestertown Historic District, and Rolphs Wharf Marina.
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 Northern Chesapeake Bay, Chesapeake Bay, or Chestertown Dog 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.

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