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

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Check availability on Chestertown Beach Hotels

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 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 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.
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.
AED 397
AED 454 total
includes taxes & fees
4 Oct - 5 Oct
The Lodge at Great Oak Landing
A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.
A two-story house with a blue exterior and a covered porch. There are two garage doors and a small outdoor seating area.
A lakeside deck with a wooden railing, a lamp post, and a grassy area leading to the water.
A wooden dock with a chair and umbrella, overlooking a calm lake with dense greenery on the shore.

2. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
AED 643
AED 1,159 total
includes taxes & fees
1 Nov - 2 Nov
Waterfront Retreat with Private Dock and Beach
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.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
AED 334
AED 374 total
includes taxes & fees
1 Nov - 2 Nov
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A hotel with a prominent sign, multiple parking spaces, and a covered entrance.
A hotel room with a sofa, a bed with a headboard, a desk, a chair, a television, and artwork on the walls.
A wedding ceremony in front of a large, classical building with steps leading up to the entrance.
A spacious lobby with a television, multiple seating options, a coffee station, and a large pillar.

4. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Edgewood
AED 285
AED 320 total
includes taxes & fees
1 Nov - 2 Nov
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
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 reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

5. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
AED 328
AED 368 total
includes taxes & fees
12 Oct - 13 Oct
Hampton Inn & Suites Edgewood/Aberdeen-South
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 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.
A modern restaurant with a bar area, seating, and a counter with a menu display.

6. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
AED 358
AED 401 total
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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 dual-monitor workstation with two chairs, a desktop computer, and framed artwork on the wall.
A gym with treadmills, elliptical machines, and a weight machine.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
AED 327
AED 367 total
includes taxes & fees
1 Nov - 2 Nov
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.
A bedroom with a bed, bedside tables, a chair, a dresser, and a closet.
A living room with a brown leather sofa, a wooden coffee table, and two armchairs.
A dining area with a wooden table, teal chairs, and a bowl of green apples.

8. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
  • A blissful beach escape awaits at this modern vacation home, just a short stroll from the shore with complimentary beach towels and bikes.
Bayside Cottage steps from Rock Hall Harbor
A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.
A hotel room with a sofa, a bed, a desk, and a lamp.
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.

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

Quality Inn & Suites Bel Air I-95 Exit 77A
Edgewood
AED 242
AED 272 total
includes taxes & fees
1 Nov - 2 Nov
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 bedroom with a large bed, a bench, a dresser, and two windows with curtains.
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
AED 479
AED 654 total
includes taxes & fees
28 Oct - 29 Oct
Kent Island Resort
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 10 hours 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.