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 1 - Sep 2
Tomorrow
Sep 2 - Sep 3
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 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'.

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 16 - Sep 17
The Lodge at Great Oak Landing
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
A modern restaurant with a bar area, seating, and a counter with a menu display.
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.

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
NT$3,085
NT$3,456 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 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.
A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.

3. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
NT$2,649
NT$2,967 total
includes taxes & fees
Sep 13 - Sep 14
Hampton Inn & Suites Edgewood/Aberdeen-South
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 hotel room with two beds, a desk with a television, a chair, and a window with curtains.
A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
NT$2,817
NT$3,155 total
includes taxes & fees
Sep 7 - Sep 8
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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 bathroom with a bathtub, toilet, sink, and a mirror.
A hotel room with a bed, a desk, a chair, a lamp, and a large cityscape painting on the wall.
A Super 8 hotel with a two-story building, a parking lot, and a grassy area with shrubs.

5. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
NT$1,770
NT$1,983 total
includes taxes & fees
Sep 6 - Sep 7
Super 8 by Wyndham Havre De Grace Aberdeen Area
A modern lobby with a curved sofa, red armchairs, a fireplace, and a dining area with green chairs.
An indoor swimming pool with lounge chairs and a hot tub, surrounded by large windows.
A hotel room with a dining area, a TV, a dresser, and a tray table.
A hotel dining area with a buffet setup, multiple dining tables, chairs, and a ceiling fan.

6. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
Bel Air
NT$3,345
NT$3,746 total
includes taxes & fees
Sep 10 - Sep 11
Homewood Suites by Hilton Bel Air
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.

7. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
NT$3,386
NT$3,911 total
includes taxes & fees
Sep 17 - Sep 18
SpringHill Suites Baltimore White Marsh/Middle River
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.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
NT$2,989
NT$3,347 total
includes taxes & fees
Sep 14 - Sep 15
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A modern kitchen with grey cabinets, a black refrigerator, a microwave, and a coffee maker.
A modern office space with a reception desk, a bar area with stools, a sofa, and a patterned rug.
A hotel with a prominent sign reading 'Candlewood Suites.'
A rectangular swimming pool with a clear blue water, surrounded by a concrete deck. There are lounge chairs and a small covered seating area.

9. Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
Bel Air
NT$2,566
NT$2,874 total
includes taxes & fees
Sep 6 - Sep 7
Candlewood Suites Aberdeen-Bel Air by IHG
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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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"good stay"
Jose 1-night trip
Posted 3 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 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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