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

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Check availability on Chestertown Beach Hotels

Tonight
Oct 3 - Oct 4
Tomorrow
Oct 4 - Oct 5
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

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 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$3,441
NT$3,934 total
includes taxes & fees
Oct 8 - Oct 9
The Lodge at Great Oak Landing
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 modern hotel lobby with a reception desk, two computer workstations, a seating area, and a decorative vase on a table.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
NT$3,223
NT$3,609 total
includes taxes & fees
Oct 11 - Oct 12
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 room with two beds, a bathroom, and a seating area.
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.

3. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
NT$3,412
NT$3,941 total
includes taxes & fees
Oct 11 - Oct 12
SpringHill Suites Baltimore White Marsh/Middle River
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 room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
NT$2,717
NT$3,043 total
includes taxes & fees
Nov 1 - Nov 2
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 coffee station with two coffee machines, a coffee press, and various coffee accessories on a wooden counter.
An aerial view of a sports complex with multiple soccer fields, parking areas, and buildings.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
NT$3,073
NT$3,442 total
includes taxes & fees
Oct 11 - Oct 12
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 gym with treadmills, elliptical machines, and a weight machine.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.
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$2,839
NT$3,179 total
includes taxes & fees
Nov 1 - Nov 2
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 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
NT$3,109
NT$3,482 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.
A lobby with a beige carpet, a reception desk, and two beige armchairs.
A bathroom with a granite countertop, sink, mirror, and toilet.
A wedding ceremony in front of a large, classical building with steps leading up to the entrance.

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

Quality Inn & Suites Bel Air I-95 Exit 77A
Edgewood
NT$2,025
NT$2,268 total
includes taxes & fees
Oct 14 - Oct 15
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 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.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.

9. Kent Island Resort

Kent Island Resort
Stevensville
NT$5,133
NT$6,782 total
includes taxes & fees
Oct 28 - Oct 29
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 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.

10. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
NT$3,494
NT$3,913 total
includes taxes & fees
Nov 2 - Nov 3
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 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.

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