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Check availability on Chestertown Cheap Hotels

Our top choices for Chestertown cheap hotels

Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is 2.609.838 ₫
2.983.828 ₫ total
includes taxes & fees
11 Dec - 12 Dec
The Lodge at Great Oak Landing
Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (858)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
The price is 2.709.223 ₫
3.007.237 ₫ total
includes taxes & fees
28 Dec - 29 Dec
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (420)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is 1.898.064 ₫
2.106.851 ₫ total
includes taxes & fees
15 Dec - 16 Dec
Red Roof Inn & Suites Chestertown
Front of property – evening/night
Driftwood Inn

Driftwood Inn

2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
The price is 1.673.987 ₫
1.858.257 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Driftwood Inn
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (599)
"very pet friendly!!"
United States
larry
The price is 2.383.125 ₫
2.669.099 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Free daily self-service breakfast
Quality Inn Smyrna

Quality Inn Smyrna

2.5 star property
Smyrna
7.6 out of 10, Good, (1000)
"Everything was great!! Checked in with ease and staff was great!!"
United States
Tonya
The price is 1.779.435 ₫
1.975.173 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn Smyrna
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1007)
"Room was great staff friendly"
United States
Melissa
The price is 2.151.139 ₫
2.409.277 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
Middletown
9.2 out of 10, Wonderful, (648)
"The room was great and the staff was even better!"
United States
STEVEN
The price is 2.398.942 ₫
2.662.826 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Express & Suites Middletown by IHG
Lobby
Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

2.5 star property
Middletown
9.2 out of 10, Wonderful, (316)
"Great overall experience "
United States
Clement
The price is 2.847.096 ₫
3.160.277 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Fairfield Inn & Suites by Marriott Middletown
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1006)
"Clean, quiet, courteous staff."
United States
MARC A
The price is 2.375.216 ₫
2.660.242 ₫ total
includes taxes & fees
4 Jan - 5 Jan 2026
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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

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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.