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Check availability on Chestertown Cheap Hotels

Our top choices for Chestertown cheap hotels

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Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (859)
"Everything was well!"
United States
Ahmed
The price is 2.678.842 ₫
2.973.514 ₫ total
includes taxes & fees
23 Dec - 24 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

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 1.894.104 ₫
2.102.455 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Red Roof Inn & Suites Chestertown
Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing

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 2.604.393 ₫
2.977.602 ₫ total
includes taxes & fees
14 Dec - 15 Dec
The Lodge at Great Oak Landing
Front of property – evening/night
Driftwood Inn

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 1.670.495 ₫
1.854.381 ₫ total
includes taxes & fees
24 Dec - 25 Dec
Driftwood Inn
Free daily self-service breakfast
Quality Inn Smyrna

Quality Inn Smyrna

Quality Inn Smyrna
2.5 star property
Smyrna
7.6 out of 10, Good, (1001)
"Everything was great"
United States
Diane
The price is 1.777.208 ₫
1.972.702 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Quality Inn Smyrna
Standard Room, 2 Queen Beds | In-room safe, desk, soundproofing, rollaway beds
Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
2.0 star property
Havre De Grace
6.6 out of 10, (967)
"It's was satisfactory "
United States
John
The price is 1.397.428 ₫
1.565.120 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Super 8 by Wyndham Havre De Grace Aberdeen Area
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (600)
"very pet friendly!!"
United States
larry
The price is 2.378.153 ₫
2.663.533 ₫ total
includes taxes & fees
19 Dec - 20 Dec
Hampton Inn & Suites Baltimore/Aberdeen
Exterior
Holiday Inn Express & Suites Middletown by IHG

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, (649)
"The room was great and the staff was even better!"
United States
STEVEN
The price is 2.446.551 ₫
2.715.672 ₫ total
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Inn Express & Suites Middletown by IHG
Reception
Hampton Inn Middletown

Hampton Inn Middletown

Hampton Inn Middletown
2.5 star property
Middletown
8.8 out of 10, Excellent, (861)
"The breakfast was was very good with lots of options depending on your dietary needs."
United States
Terry
The price is 2.441.290 ₫
2.709.621 ₫ total
includes taxes & fees
7 Jan - 8 Jan 2026
Hampton Inn Middletown
Terrace/patio
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (337)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
The price is 1.830.967 ₫
2.050.683 ₫ total
includes taxes & fees
10 Jan - 11 Jan 2026
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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.