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

Find Beach Hotels in Chestertown, MD

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Beach Hotels

Tonight
Sep 26 - Sep 27
Tomorrow
Sep 27 - Sep 28
Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11

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 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.
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$3,430
NT$3,921 total
includes taxes & fees
Sep 27 - Sep 28
The Lodge at Great Oak Landing
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
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.
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 modern restaurant with a bar area, seating, and a counter with a menu display.

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
NT$3,106
NT$3,479 total
includes taxes & fees
Oct 4 - Oct 5
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A hotel room with two beds, a nightstand with a lamp, and a wooden headboard.
A hotel reception desk with a blue wall featuring the Holiday Inn Express logo, a check-in/out sign, and a 'No Pets' sign.
A coffee station with two coffee machines, a coffee press, and various coffee accessories on a wooden counter.
A modern bathroom with a large mirror, white sink, and towel rack.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
NT$2,763
NT$3,094 total
includes taxes & fees
Oct 27 - Oct 28
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A hotel entrance with a clear sign reading "LA QUINTA".
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.
A hotel lobby with multiple dining tables and chairs, a reception area with a counter and a television, and large windows with red curtains.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
NT$3,023
NT$3,386 total
includes taxes & fees
Oct 2 - Oct 3
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.
A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.

5. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
NT$2,714
NT$3,040 total
includes taxes & fees
Oct 4 - Oct 5
Hampton Inn & Suites Edgewood/Aberdeen-South
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.
A gym with treadmills, elliptical machines, and a weight machine.
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
NT$2,994
NT$3,353 total
includes taxes & fees
Oct 25 - Oct 26
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A bathroom with a shower, toilet, and sink.
A Ramada hotel with a two-story structure, multiple balconies, and a parking lot.
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.

7. Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
Edgewood
NT$2,672
NT$2,993 total
includes taxes & fees
Sep 27 - Sep 28
Ramada Hotel & Conference Center by Wyndham Edgewood
A large, two-story barn-style building with a covered front porch and a garage.
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.
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.

8. Kent Island Resort

Kent Island Resort
Stevensville
NT$4,861
NT$6,470 total
includes taxes & fees
Oct 19 - Oct 20
Kent Island Resort
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 hotel room with a bed, a desk, a chair, a lamp, and a large cityscape painting on the wall.
A bathroom with a bathtub, toilet, sink, and a mirror.

9. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
NT$1,727
NT$1,935 total
includes taxes & fees
Sep 28 - Sep 29
Super 8 by Wyndham Havre De Grace Aberdeen Area
View all properties

Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included
4 stars
5 stars
All-inclusive

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Overall the job couldn’t have been done better…"
Ahmed 2-night trip
Posted 17 hours ago
Comfort Inn & Suites Chestertown

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 River Arts Chestertown. For more things to see and do, consider visiting Historical Society of Kent County Maryland or Chestertown Historic District.
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.

Explore a world of travel with Expedia