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 13 - Oct 14
Tomorrow
Oct 14 - Oct 15
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 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 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.
NT$3,448
NT$3,942 total
includes taxes & fees
Oct 14 - Oct 15
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.
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
NT$3,419
NT$3,949 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 room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.

3. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
NT$2,722
NT$3,049 total
includes taxes & fees
Nov 2 - Nov 3
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.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
NT$2,650
NT$2,968 total
includes taxes & fees
Nov 10 - Nov 11
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
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.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
NT$3,419
NT$3,830 total
includes taxes & fees
Oct 15 - Oct 16
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
A dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.
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.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
NT$2,844
NT$3,186 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.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.
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 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
NT$3,115
NT$3,489 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 modern building with a stone facade, large windows, and outdoor seating area with chairs.
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
NT$3,365
NT$3,769 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Bel Air
A large, two-story barn-style building with a covered front porch and a garage.
A bedroom with a large bed, a bench, a dresser, and two windows with curtains.
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 covered porch with white railings and a table with chairs.

9. Kent Island Resort

Kent Island Resort
Stevensville
NT$3,864
NT$5,343 total
includes taxes & fees
Oct 28 - Oct 29
Kent Island Resort
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 hotel room with a sofa, a bed, a desk, and a lamp.
A wedding ceremony in front of a large, classical building with steps leading up to the entrance.

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

Quality Inn & Suites Bel Air I-95 Exit 77A
Edgewood
NT$1,958
NT$2,193 total
includes taxes & fees
Oct 26 - Oct 27
Quality Inn & Suites Bel Air I-95 Exit 77A
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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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