The Best Beach Hotels in Chestertown, MD from NT$2,353 in 2026

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

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Our top choices for Chestertown beach hotels

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

1. 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$4,003 total

includes taxes & fees

Nov 1 - Nov 2

A buffet area with multiple self-service stations, including trays of omelets and other prepared foods.

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

Edgewood

NT$3,195 total

includes taxes & fees

Nov 2 - Nov 3

A modern hotel lobby with a long dining table, several chairs, and a bar area.

3. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

NT$3,097 total

includes taxes & fees

Nov 22 - Nov 23

A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

4. SpringHill Suites Baltimore White Marsh/Middle River

Middle River

NT$4,011 total

includes taxes & fees

Nov 8 - Nov 9

A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

5. Hilton Garden Inn Bel Air

Bel Air

NT$3,796 total

includes taxes & fees

Nov 29 - Nov 30

A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

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

Bel Air

NT$3,235 total

includes taxes & fees

Nov 8 - Nov 9

An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

NT$3,543 total

includes taxes & fees

Nov 8 - Nov 9

A hotel with a prominent sign, multiple parking spaces, and a covered entrance.

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

Edgewood

NT$2,929 total

includes taxes & fees

Nov 24 - Nov 25

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Breakfast included

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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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Check availability on Chestertown Beach Hotels

Our top choices for Chestertown beach hotels

1. The Lodge at Great Oak Landing

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

3. Hampton Inn & Suites Edgewood/Aberdeen-South

4. SpringHill Suites Baltimore White Marsh/Middle River

5. Hilton Garden Inn Bel Air

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

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

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

9. Ramada Hotel & Conference Center by Wyndham Edgewood

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

Choose what matters most at beach hotels in Chestertown

Top Chestertown Hotel Reviews

Frequently asked questions

Explore a world of travel with Expedia

Find Beach Hotels in Chestertown, MD

Change your mind

Treat yourself

Be picky

Check availability on Chestertown Beach Hotels

Our top choices for Chestertown beach hotels

1. The Lodge at Great Oak Landing

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

3. Hampton Inn & Suites Edgewood/Aberdeen-South

4. SpringHill Suites Baltimore White Marsh/Middle River

5. Hilton Garden Inn Bel Air

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

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

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

9. Ramada Hotel & Conference Center by Wyndham Edgewood

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

Choose what matters most at beach hotels in Chestertown

Top Chestertown Hotel Reviews

Frequently asked questions

Explore a world of travel with Expedia