The Best Beach Hotels in Chestertown, MD from NT$2,027 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

Private beach nearby, sun loungers, beach volleyball

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$3,483

NT$3,982 total

includes taxes & fees

Aug 9 - Aug 10

Desk, laptop workspace, blackout drapes, iron/ironing board

2. SpringHill Suites Baltimore White Marsh/Middle River

Middle River

NT$3,454

NT$3,989 total

includes taxes & fees

Aug 13 - Aug 14

Suite, 1 Queen Bed | Living area | 50-inch flat-screen TV with cable channels, TV

3. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Aberdeen

NT$3,147

NT$3,524 total

includes taxes & fees

Aug 30 - Aug 31

4. Fairfield Inn & Suites by Marriott Aberdeen

Aberdeen

NT$3,531

NT$3,954 total

includes taxes & fees

Aug 9 - Aug 10

Studio Suite, Multiple Beds, Non Smoking | WiFi (free), bed sheets

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

Edgewood

NT$2,419

NT$2,709 total

includes taxes & fees

Aug 10 - Aug 11

Desk, blackout drapes, iron/ironing board, cribs/infant beds

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

Edgewood

NT$2,741

NT$3,070 total

includes taxes & fees

Sep 7 - Sep 8

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

Bel Air

NT$2,873

NT$3,218 total

includes taxes & fees

Sep 6 - Sep 7

8. Hilton Garden Inn Bel Air

Bel Air

NT$3,676

NT$4,117 total

includes taxes & fees

Aug 30 - Aug 31

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Choose what matters most at beach hotels in Chestertown

Pool

Breakfast included

4 stars

5 stars

All-inclusive

Top Chestertown Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"Staff was wonderful and friendly, and our room was impeccably clean. Breakfast was simple but had the essentials!"

Comfort Inn & Suites Chestertown

8/10 Good

"Hotel was fine. Area was a little sketchy."

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 a seasonal outdoor pool and free WiFi, 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 Chestertown Historic District. For more things to see and do, consider visiting Rolphs Wharf Marina or Northern Chesapeake Bay.

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. SpringHill Suites Baltimore White Marsh/Middle River

3. Home2 Suites by Hilton Baltimore / Aberdeen, MD

4. Fairfield Inn & Suites by Marriott Aberdeen

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

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

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

8. Hilton Garden Inn Bel Air

9. Super 8 by Wyndham Aberdeen MD

10. Ramada Hotel & Conference Center by Wyndham Edgewood

Choose what matters most at beach hotels in Chestertown

Top Chestertown Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

Comfort Inn & Suites Chestertown

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. SpringHill Suites Baltimore White Marsh/Middle River

3. Home2 Suites by Hilton Baltimore / Aberdeen, MD

4. Fairfield Inn & Suites by Marriott Aberdeen

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

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

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

8. Hilton Garden Inn Bel Air

9. Super 8 by Wyndham Aberdeen MD

10. Ramada Hotel & Conference Center by Wyndham Edgewood

Choose what matters most at beach hotels in Chestertown

Top Chestertown Hotel Reviews

Holiday Inn Express Annapolis East-Kent Island by IHG

Comfort Inn & Suites Chestertown

Frequently asked questions

Explore a world of travel with Expedia