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

Chestertown Hotel Guide - Beach Hotels in Chestertown, Maryland

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Beach Hotels

Tonight
13 Oct - 14 Oct
Tomorrow
14 Oct - 15 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 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 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 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.
€110
includes taxes & fees
14 Oct - 15 Oct
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.
An outdoor patio with brick walls, green chairs, and a fire pit.
A hotel room with two beds, a bathroom, and a seating area.

2. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
€110
includes taxes & fees
25 Oct - 26 Oct
SpringHill Suites Baltimore White Marsh/Middle River
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.

3. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
€85
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
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.
An aerial view of a sports complex with multiple soccer fields, parking areas, and buildings.
A coffee station with two coffee machines, a coffee press, and various coffee accessories on a wooden counter.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
€83
includes taxes & fees
11 Nov - 12 Nov
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
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.

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

La Quinta Inn & Suites by Wyndham Aberdeen-APG
Aberdeen
€108
includes taxes & fees
14 Oct - 15 Oct
La Quinta Inn & Suites by Wyndham Aberdeen-APG
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.
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.
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
€89
includes taxes & fees
1 Nov - 2 Nov
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 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 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.

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
€98
includes taxes & fees
1 Nov - 2 Nov
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 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.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.

8. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
€106
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Bel Air
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.

9. Kent Island Resort

Kent Island Resort
Stevensville
€149
includes taxes & fees
28 Oct - 29 Oct
Kent Island Resort
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 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.

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

Quality Inn & Suites Bel Air I-95 Exit 77A
Edgewood
€61
includes taxes & fees
26 Oct - 27 Oct
Quality Inn & Suites Bel Air I-95 Exit 77A
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

Frequently asked questions

What is Chestertown like for travellers who love the beach?
Known for its university life, Chestertown offers a lot for the traveller planning a getaway.
What's the best place to stay for a beach holiday 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 for your stay near the beach.
When's the best time for a beach holiday in Chestertown?
You can plan your beach trip with this snapshot of year-round temperatures in Chestertown: The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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 such as 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 centre. If you'd like to venture out around the area, you may want to rent a car for your trip.