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

Chestertown Beach Resorts from RM291

  • 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 Resorts

Tonight
4 Oct - 5 Oct
Tomorrow
5 Oct - 6 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

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 large brick building with a symmetrical facade, multiple chimneys, and a central entrance.
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 marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

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.
RM441
RM504 total
includes taxes & fees
14 Oct - 15 Oct
The Lodge at Great Oak Landing
A hotel entrance with a clear sign reading "LA QUINTA".
A hotel room with a bed, a desk with a chair, a television, and artwork on the wall.
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.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
RM413
RM463 total
includes taxes & fees
11 Oct - 12 Oct
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.
A hotel with a modern facade, a covered entrance, and a red car parked outside.
A modern bathroom with a large mirror, two sinks, and a glass-enclosed shower.
An outdoor patio with brick walls, green chairs, and a fire pit.

3. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
RM437
RM505 total
includes taxes & fees
8 Oct - 9 Oct
SpringHill Suites Baltimore White Marsh/Middle River
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 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.

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
RM348
RM390 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
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 modern bathroom with a large mirror, white sink, and towel rack.
A coffee station with two coffee machines, a coffee press, and various coffee accessories on a wooden counter.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
RM339
RM380 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
A Country Inn & Suites hotel with a brick facade, multiple windows, and a sign indicating the entrance.
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.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
RM364
RM408 total
includes taxes & fees
1 Nov - 2 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.
A modern restaurant with a bar area, seating, and a counter with a menu display.

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
RM399
RM446 total
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.
A bathroom with a granite countertop, sink, mirror, and toilet.
A lobby with a beige carpet, a reception desk, and two beige armchairs.
A hotel room with a sofa, a bed, a desk, and a lamp.

8. Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A
Edgewood
RM260
RM291 total
includes taxes & fees
14 Oct - 15 Oct
Quality Inn & Suites Bel Air I-95 Exit 77A
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 bedroom with a large bed, a bench, a dresser, and two windows with curtains.
A covered porch with white railings and a table with chairs.

9. Kent Island Resort

Kent Island Resort
Stevensville
RM658
RM869 total
includes taxes & fees
28 Oct - 29 Oct
Kent Island Resort
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.
A modern building with a stone facade, large windows, and outdoor seating area with chairs.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.

10. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
RM448
RM502 total
includes taxes & fees
2 Nov - 3 Nov
Hilton Garden Inn Bel Air
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

10/10 Excellent
"Had a good time. Nice area"
Thomas E 3-night trip
Posted 3 days ago
Hilton Garden Inn Kent Island Marina

Frequently asked questions

What is Chestertown like for travellers who love the beach?
Known for its university life, Chestertown offers a lot for the traveller planning a getaway.
What's the best place to stay for a beach holiday 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 for your stay near the beach.
When's the best time for a beach holiday in Chestertown?
You can plan your beach trip with this snapshot of year-round temperatures in Chestertown: 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 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 such as 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 centre. If you'd like to venture out around the area, you may want to rent a car for your trip.

Explore a world of travel with Expedia