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

Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Tonight
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
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 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.
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.

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$3,415
NT$3,904 total
includes taxes & fees
Sep 2 - Sep 3
The Lodge at Great Oak Landing
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
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.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
NT$3,093
NT$3,464 total
includes taxes & fees
Sep 7 - Sep 8
Home2 Suites by Hilton Baltimore / 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 pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.
A hotel room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.

3. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
NT$2,645
NT$2,962 total
includes taxes & fees
Sep 6 - Sep 7
Hampton Inn & Suites Edgewood/Aberdeen-South
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
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.
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
NT$2,824
NT$3,163 total
includes taxes & fees
Sep 7 - Sep 8
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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.
A bathroom with a white sink, a mirror, and a towel dispenser.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
NT$2,751
NT$3,081 total
includes taxes & fees
Sep 28 - Sep 29
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 Super 8 hotel with a two-story building, a parking lot, and a grassy area with shrubs.
A bathroom with a bathtub, toilet, sink, and a mirror.
A reception area with a wooden counter, a potted plant, a refrigerator, and a table.

6. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
NT$1,767
NT$1,979 total
includes taxes & fees
Sep 1 - Sep 2
Super 8 by Wyndham Havre De Grace Aberdeen Area
A hotel entrance with a clear sign reading "LA QUINTA".
A modern hotel lobby with a reception desk, two computer workstations, a seating area, and a decorative vase on a table.
A hotel lobby with seating areas, a TV on the wall, and patterned curtains.
A hotel room with a bed, a desk with a chair, a television, and artwork on the wall.

7. La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
NT$3,010
NT$3,371 total
includes taxes & fees
Sep 5 - Sep 6
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A large, two-story barn-style building with a covered front porch and a garage.
A covered porch with white railings and a table with chairs.
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.

8. Kent Island Resort

Kent Island Resort
Stevensville
NT$5,117
NT$6,756 total
includes taxes & fees
Sep 14 - Sep 15
Kent Island Resort
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 lobby with a checkered wall, a flat-screen TV, a painting, a patterned carpet, and red upholstered chairs.
A hotel room with a large bed, a desk, and a chair.

9. Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
Edgewood
NT$2,253
NT$2,524 total
includes taxes & fees
Aug 31 - Sep 1
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

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent
"Great view of the water."
LINDA 1-night trip
Posted 1 day ago
Holiday Inn Express Annapolis East-Kent Island by IHG

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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