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

Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Tonight
Oct 1 - Oct 2
Tomorrow
Oct 2 - Oct 3
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

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 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 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.
NT$3,440
NT$3,933 total
includes taxes & fees
Oct 8 - Oct 9
The Lodge at Great Oak Landing
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.

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

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
NT$2,899
NT$3,247 total
includes taxes & fees
Nov 1 - Nov 2
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 hotel lobby with a reception desk, seating area, and a large screen.
A spacious lobby with a television, multiple seating options, a coffee station, and a large pillar.

3. 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
NT$2,475
NT$2,772 total
includes taxes & fees
Nov 1 - Nov 2
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 pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.
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$2,847
NT$3,189 total
includes taxes & fees
Oct 15 - Oct 16
Hampton Inn & Suites Edgewood/Aberdeen-South
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 modern restaurant with a bar area, seating, and a counter with a menu display.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.

5. 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 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 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.

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
NT$2,838
NT$3,179 total
includes taxes & fees
Nov 1 - Nov 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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 lobby with a beige carpet, a reception desk, and two beige armchairs.
A hotel room with a sofa, a bed, a desk, and a lamp.

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

Quality Inn & Suites Bel Air I-95 Exit 77A
Edgewood
NT$2,103
NT$2,355 total
includes taxes & fees
Nov 1 - Nov 2
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 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.

8. Kent Island Resort

Kent Island Resort
Stevensville
NT$4,619
NT$6,198 total
includes taxes & fees
Oct 28 - Oct 29
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 13 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.

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