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

Chestertown Cheap Hotels

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Check availability on Chestertown Cheap Hotels

Tonight
18 Oct - 19 Oct
Tomorrow
19 Oct - 20 Oct
Next weekend
23 Oct - 25 Oct
In two weeks
30 Oct - 1 Nov
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 brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
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
HK$766
HK$850 total
includes taxes & fees
8 Nov - 9 Nov
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 sign with a red background and white lettering, a parking lot, and a building with a brick facade.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Kate
HK$565
HK$627 total
includes taxes & fees
25 Oct - 26 Oct
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.
A two-story building with a brick facade, large windows, and a sloped roof.
A living room with two patterned armchairs, a wooden coffee table, and a standing fan.
A living room with a wooden cabinet, a television, a sofa, and a dining table.

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
HK$498
HK$553 total
includes taxes & fees
19 Oct - 20 Oct
Driftwood Inn
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
A campfire in a stone fire pit by a lakeside at sunset.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

4. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Steve allen
HK$848
HK$969 total
includes taxes & fees
19 Oct - 20 Oct
The Lodge at Great Oak Landing
A house with a swimming pool, surrounded by a fence, and two red umbrellas.
A bedroom with a bed, a ceiling fan, a painting, and a door leading to another room.
A closet with a wooden floor, a white door, and a blue bag on top.
A swimming pool with a curved edge, surrounded by a brick patio and a hedge.

5. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
United States
John R.
HK$777
HK$1,247 total
includes taxes & fees
19 Oct - 20 Oct
First Floor Studio Apartment in Historic Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.
A bedroom with a large bed, a nightstand, a lamp, a patterned rug, and a view through an open door to a hallway.
A modern kitchen with a large island, white cabinetry, and a view of the city.
A modern kitchen with white cabinets, a central island, and pendant lighting.

6. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
United States
Susan A.
HK$1,766
HK$2,772 total
includes taxes & fees
19 Oct - 20 Oct
Newly restored apartment in the heart of Chestertown
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.
A residential property with a wooden exterior, a visible front door, and a garden area with various plants.
A bedroom with a wooden bed, a nightstand, a dresser, and a rug.
A kitchen with wooden cabinets, a white dishwasher, a microwave, a coffee maker, and a clock on the wall.

7. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
United States
Amy D.
HK$1,441
HK$2,150 total
includes taxes & fees
25 Oct - 26 Oct
Secluded Cottage in Middle of Chestertown
A hallway with wooden flooring, a door on the right, and a window at the end.
A bedroom with a four-poster bed, wooden shelving with books and decorative items, and a fireplace.
A wooden door, a rug, a cabinet, and a lamp.
A two-story house with a covered patio and a lawn.

8. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
United States
Mandy D.
HK$2,458
HK$3,857 total
includes taxes & fees
16 Nov - 17 Nov
Wren Retweet- Country Estate in Center of C’Town
A deck with outdoor furniture, a potted plant, and a house in the background.
A bedroom with a bed, a ceiling fan, a door, and a view of the outdoors.
A compact kitchen with a built-in microwave, oven, and sink. There's a dining area with a wooden table and chairs.
A modern living room with a sofa, a coffee table, and a ceiling fan.

9. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
United States
Miriam G.
HK$1,727
HK$2,429 total
includes taxes & fees
26 Oct - 27 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A boat deck with a white bench and a view of a calm lake and distant trees.
A sunflower field with a white barn and a large house in the background.
A buffet with various food items including fruits, pastries, and salads.
A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.

10. Inn at Huntingfield Creek

Inn at Huntingfield Creek
Rock Hall
United States
Christine
HK$1,100
HK$1,221 total
includes taxes & fees
16 Nov - 17 Nov
Inn at Huntingfield Creek
View all properties

Top Chestertown Hotel Reviews

Country Inn & Suites by Radisson, Baltimore North, MD

Country Inn & Suites by Radisson, Baltimore North, MD

10/10 Excellent
"I stayed here for a mini staycation and was not disappointed. The parking situation was easy, the room was very nice, and the continental breakfast was great! The staff were very friendly and helpful, which is always a plus in my book. The close proximity to restaurants and some shops was another bonus. I have no complaints whatsoever and would definitely stay here again."
Cara 1-night trip
Posted 8 hours ago
Country Inn & Suites by Radisson, Baltimore North, MD
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

10/10 Excellent
"Good."
Dexter 1-night trip
Posted 9 hours ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Frequently asked questions

What is Chestertown like for travellers on a budget?
Chestertown has cheap accommodation options and a range of things to see and do, making it a great holiday choice for budget-conscious travellers. You can find ways to save money while getting to know this destination, which is home to attractions such as 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, but bear 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 temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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 fill your itinerary with 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?
Looking at these ways to get around Chestertown is a smart way to keep your trip affordable. The nearest airport is 20.3 mi (32.7 km) away from the centre in Baltimore, MD (MTN-Martin State). If that doesn't suit your budget, you can book a flight to Easton, MD (ESN-Easton - Newnam), located 28.2 mi (45.3 km) away. Chestertown may not have many public transport options to choose from so a car rental could be a reasonable alternative to explore more of the area.

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