The Best Beach Hotels in Chestertown, MD from NT$2,052 in 2026

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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$4,056 total

includes taxes & fees

Nov 11 - Nov 12

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

2. Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

NT$3,138 total

includes taxes & fees

Nov 23 - Nov 24

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

3. SpringHill Suites Baltimore White Marsh/Middle River

Middle River

NT$4,064 total

includes taxes & fees

Nov 15 - Nov 16

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

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

Edgewood

NT$2,576 total

includes taxes & fees

Nov 12 - Nov 13

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$3,722 total

includes taxes & fees

Dec 3 - Dec 4

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

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

Edgewood

NT$3,054 total

includes taxes & fees

Dec 7 - Dec 8

A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.

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

Edgewood

NT$2,299 total

includes taxes & fees

Nov 10 - Nov 11

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

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

Bel Air

NT$3,202 total

includes taxes & fees

Nov 29 - Nov 30

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

9. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

NT$3,590 total

includes taxes & fees

Nov 22 - Nov 23

An outdoor patio with seating, a fire pit, and a barbecue area.

10. TownePlace Suites by Marriott Edgewood Aberdeen

Aberdeen

NT$4,121 total

includes taxes & fees

Nov 25 - Nov 26

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Choose what matters most at beach hotels in Chestertown

Pool

Breakfast included

Top Chestertown Hotel Reviews

The Lodge at Great Oak Landing

Chestertown

10/10 Excellent

William

Hampton Inn & Suites Edgewood/Aberdeen-South

Edgewood

10/10 Excellent

John

Hilton Garden Inn Bel Air

Bel Air

10/10 Excellent

Ami

SpringHill Suites Baltimore White Marsh/Middle River

Middle River

10/10 Excellent

Rachael

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

The Inn at Chesapeake Bay Beach Club

Stevensville

10/10 Excellent

Chuck

A large, two-story barn-style building with a covered front porch and a garage.

Kent Island Resort

Stevensville

10/10 Excellent

I stayed here for a quick overnight and did not utilize many of the amenities however, the staff was incredibly kind overall and with tips on dinner. This place is historic, which is a nice way of saying old but classic. Don’t expect a huge room, the photos portray the room accurately. Some things were a little rickety, but everything was clean. Overall I recommend this if you’re solo or a couple looking for a place as you enjoy the bay.

John

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Edgewood

10/10 Excellent

Heather

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

Bel Air

10/10 Excellent

Lori

A hotel entrance with a clear sign reading "LA QUINTA".

City Express by Marriott Aberdeen

Aberdeen

10/10 Excellent

Pamela

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

10/10 Excellent

Terry

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

Edgewood

10/10 Excellent

Mansoor

An outdoor patio area with wicker furniture, a fire pit, and umbrellas.

Fairfield Inn & Suites by Marriott Aberdeen

Aberdeen

10/10 Excellent

Marianne

Holiday Inn Belcamp - Aberdeen Area by IHG

Belcamp

10/10 Excellent

Evelyn

A spacious indoor area with brick walls, wooden flooring, and string lights. There are tables and chairs arranged for dining or socializing.

Historic Inns of Annapolis

Historic District

10/10 Excellent

Robert

A white two-story building with a central entrance, a staircase, and a small garden area.

134 Prince - Luxury Boutique Hotel

Annapolis

10/10 Excellent

Reyna

An outdoor patio with tables and chairs, a black umbrella, and string lights.

Holiday Inn Express Aberdeen by IHG

Aberdeen

10/10 Excellent

Anna

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.

Find Beach Hotels in Chestertown, MD

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chestertown beach hotels

1. The Lodge at Great Oak Landing

2. Hampton Inn & Suites Edgewood/Aberdeen-South

3. SpringHill Suites Baltimore White Marsh/Middle River

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

5. Hilton Garden Inn Bel Air

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

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

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

9. Home2 Suites by Hilton Baltimore / Aberdeen, MD

10. TownePlace Suites by Marriott Edgewood Aberdeen

Choose what matters most at beach hotels in Chestertown

Top Chestertown Hotel Reviews

The Lodge at Great Oak Landing

10/10 Excellent

Frequently Asked Questions

What is Chestertown like for travelers who love the beach?

What's the best hotel for a beach vacation in Chestertown?

When's the best time for a beach vacation in Chestertown?

What is there to see and do around Chestertown?

What's the best way to get to my beach hotel in Chestertown?

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