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

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Check availability on Chestertown Beach Hotels

Tonight
Sep 2 - Sep 3
Tomorrow
Sep 3 - Sep 4
This weekend
Sep 4 - Sep 6
Next weekend
Sep 11 - Sep 13

Our top choices for Chestertown beach hotels

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
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'.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.

1. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
  • Escape to waterfront tranquility with a private beach just 0.25 miles away, where sandy shores, volleyball courts, and loungers await.
NT$3,419
NT$3,908 total
includes taxes & fees
Sep 9 - Sep 10
The Lodge at Great Oak Landing
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.
A hotel room with a desk, office chair, sofa, and a dining table with chairs. There is a window with blinds, a painting on the wall, and a door leading to another room.
A multi-story hotel with a modern facade, featuring a prominent 'HOME 2' sign. The entrance is accessible via a covered walkway, and the building is equipped with large windows and a flagpole.

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
NT$3,218
NT$3,605 total
includes taxes & fees
Sep 9 - Sep 10
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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 gym with treadmills, elliptical machines, and a weight machine.
A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
NT$2,835
NT$3,175 total
includes taxes & fees
Sep 9 - Sep 10
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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 reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
NT$2,673
NT$2,994 total
includes taxes & fees
Sep 9 - Sep 10
Hampton Inn & Suites Edgewood/Aberdeen-South
An aerial view of a sports complex with multiple soccer fields, parking areas, and buildings.
A hotel room with two beds, a nightstand with a lamp, and a wooden headboard.
A hotel entrance with a covered driveway, flag, and a parking lot.
A modern office with a desk, two chairs, a computer, and a lamp. Large windows provide a view of the outdoors.

5. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
NT$2,754
NT$3,084 total
includes taxes & fees
Sep 30 - Oct 1
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A breakfast counter with a black-and-white photo of a historic building, a bowl of apples, a container of bread, and a coffee machine.
A reception area with a wooden counter, a potted plant, a refrigerator, and a table.
A Super 8 hotel with a two-story building, a parking lot, and a grassy area with shrubs.
A hotel room with a bed, a desk, a chair, a lamp, and a large cityscape painting on the wall.

6. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
NT$1,769
NT$1,981 total
includes taxes & fees
Sep 7 - Sep 8
Super 8 by Wyndham Havre De Grace Aberdeen Area
A large, two-story barn-style building with a covered front porch and a garage.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.
A modern bathroom with a glass shower enclosure, a white toilet, and a vanity with a mirror.
A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

7. Kent Island Resort

Kent Island Resort
Stevensville
NT$5,170
NT$6,817 total
includes taxes & fees
Sep 30 - Oct 1
Kent Island Resort
A hotel lobby with a reception desk, seating area, and a fireplace.
A modern living room with a gray sofa, a wooden coffee table, and framed pictures on the wall.
A hotel lobby with two blue armchairs, a round mirror, a framed picture of a building, and a table with a lamp.
A spacious dining area with multiple tables and chairs, large windows, and a modern ceiling design.

8. Comfort Inn & Suites Aberdeen near APG

Comfort Inn & Suites Aberdeen near APG
Aberdeen
NT$2,131
NT$2,387 total
includes taxes & fees
Sep 24 - Sep 25
Comfort Inn & Suites Aberdeen near APG
A bathroom with a shower, toilet, and sink.
A hotel dining area with a kitchen in the background, featuring a bar and seating arrangements.
A hotel room with a large bed, a desk, and a chair.
A Ramada hotel with a two-story structure, multiple balconies, and a parking lot.

9. Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
Edgewood
NT$2,664
NT$2,983 total
includes taxes & fees
Sep 26 - Sep 27
Ramada Hotel & Conference Center by Wyndham Edgewood
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Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included
4 stars
5 stars
All-inclusive

Top Chestertown Hotel Reviews

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

10/10 Excellent
"Close to the bay"
Joshua 1-night trip
Posted 1 day ago
Best Western Kent Narrows Inn

Frequently asked questions

What is Chestertown like for travelers who love the beach?
Known for its university life, Chestertown offers a lot for the traveler planning a getaway.
What's the best hotel for a beach vacation in Chestertown?
The Lodge at Great Oak Landing is a top lodge with 2 restaurants and a seasonal outdoor pool, and it's located near a private beach. Great Oak Manor is another good option to stay near the beach.
When's the best time for a beach vacation in Chestertown?
You can plan your beach trip with this snapshot of the seasons in Chestertown: 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 around Chestertown?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. Beach lovers can head straight to Betterton Beach or Main Beach for some quality time by the water. Experience the area's university life, and make time for local attractions like Washington College and Chestertown Historic District. For more things to see and do, consider visiting Northern Chesapeake Bay or Chesapeake Bay.
What's the best way to get to my beach hotel in Chestertown?
Here's some information to help you get to and around your beach accommodation in Chestertown more easily: To get to Chestertown, book a flight to Baltimore, MD (MTN-Martin State), the closest major airport, which is located 20.3 mi (32.7 km) from the city center. If you'd like to venture out around the area, you may want a rental car for your journey.

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