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 14 - Oct 15
Tomorrow
Oct 15 - Oct 16
This weekend
Oct 16 - Oct 18
Next weekend
Oct 23 - Oct 25

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 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.

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.
₩145,125
₩165,921 total
includes taxes & fees
Oct 18 - Oct 19
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 hotel with a modern facade, a covered entrance, and a red car parked outside.
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.

2. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
₩143,916
₩166,223 total
includes taxes & fees
Oct 18 - Oct 19
SpringHill Suites Baltimore White Marsh/Middle River
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 kitchenette, a large mirror, a window with curtains, a desk, and a chair.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

3. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
₩113,832
₩127,492 total
includes taxes & fees
Nov 2 - Nov 3
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 seating areas, a TV on the wall, and patterned curtains.
A modern hotel lobby with a reception desk, two computer workstations, a seating area, and a decorative vase on a table.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
₩143,915
₩161,185 total
includes taxes & fees
Oct 15 - Oct 16
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A hotel room with two beds, a nightstand with a lamp, and a wooden headboard.
A modern bathroom with a large mirror, white sink, and towel rack.
A hotel reception desk with a blue wall featuring the Holiday Inn Express logo, a check-in/out sign, and a 'No Pets' sign.
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
₩110,788
₩124,082 total
includes taxes & fees
Nov 11 - Nov 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 dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.
A hotel room with two beds, a desk with a television, a chair, and a window with curtains.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
₩118,931
₩133,201 total
includes taxes & fees
Nov 2 - Nov 3
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.
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.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
₩131,123
₩146,857 total
includes taxes & fees
Nov 1 - Nov 2
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.
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.

8. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
₩141,631
₩158,627 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Bel Air
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 wedding ceremony in front of a large, classical building with steps leading up to the entrance.
A lobby with a beige carpet, a reception desk, and two beige armchairs.

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

Quality Inn & Suites Bel Air I-95 Exit 77A
Edgewood
₩82,412
₩92,302 total
includes taxes & fees
Oct 26 - Oct 27
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 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 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.

10. Kent Island Resort

Kent Island Resort
Stevensville
₩164,424
₩226,934 total
includes taxes & fees
Oct 29 - Oct 30
Kent Island Resort
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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

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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