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

Beach Resorts in Chestertown

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Check availability on Chestertown Beach Resorts

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
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 marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
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.
S$158
includes taxes & fees
20 Oct - 21 Oct
The Lodge at Great Oak Landing
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.
A modern bathroom with a large mirror, two sinks, and a glass-enclosed shower.
A hotel with a modern facade, a covered entrance, and a red car parked outside.
An outdoor patio with brick walls, green chairs, and a fire pit.

2. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
S$158
includes taxes & fees
18 Oct - 19 Oct
SpringHill Suites Baltimore White Marsh/Middle River
A hotel room with two beds, a nightstand with a lamp, and a wooden headboard.
An aerial view of a sports complex with multiple soccer fields, parking areas, and buildings.
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
S$119
includes taxes & fees
9 Nov - 10 Nov
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.
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.

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
S$122
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
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 hotel lobby with multiple dining tables and chairs, a reception area with a counter and a television, and large windows with red curtains.
A hotel lobby with seating areas, a TV on the wall, and patterned curtains.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
S$153
includes taxes & fees
12 Oct - 13 Oct
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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 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.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
S$128
includes taxes & fees
2 Nov - 3 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.
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.
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.

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
S$140
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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 bedroom with a large bed, a bench, a dresser, and two windows with curtains.

8. Kent Island Resort

Kent Island Resort
Stevensville
S$214
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 spacious lobby with a beige sofa, blue armchairs, and a wooden coffee table. There are two floor lamps and a small round table.
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.

9. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
S$157
includes taxes & fees
2 Nov - 3 Nov
Hilton Garden Inn Bel Air
A bathroom with a shower, toilet, and sink.
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.
A Ramada hotel with a two-story structure, multiple balconies, and a parking lot.

10. Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
Edgewood
S$121
includes taxes & fees
16 Oct - 17 Oct
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
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Top Chestertown Hotel Reviews

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.

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