Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Our top choices for Chestertown beach hotels

Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is ₩146,152
₩167,095 total
includes taxes & fees
Dec 23 - Dec 24
The Lodge at Great Oak Landing
Terrace/patio
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (337)
"The breakfast menu was okay but not great. The overall hotel was very nice and the staff were friendly."
United States
Gregory
The price is ₩105,318
₩117,956 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Exterior
La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1003)
"Nice place"
United States
Maria
The price is ₩131,809
₩147,625 total
includes taxes & fees
Jan 4 - Jan 5, 2026
La Quinta Inn & Suites by Wyndham Aberdeen-APG
In-room safe, individually furnished, desk, laptop workspace
Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG

Candlewood Suites Aberdeen-Bel Air by IHG
2.5 star property
Bel Air
8.0 out of 10, Very Good, (470)
"Good room and service "
United States
Robert
The price is ₩122,531
₩137,235 total
includes taxes & fees
Dec 25 - Dec 26
Candlewood Suites Aberdeen-Bel Air by IHG
Bar (on property)
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (228)
"Wonderful staff! So nice, clean and comfortable. Will definitely stay there again."
United States
Melissa
The price is ₩143,553
₩160,779 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Hilton Garden Inn Bel Air
Reception
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (128)
"Beautiful and peaceful property!"
United States
Jerry
The price is ₩211,459
₩287,466 total
includes taxes & fees
Dec 22 - Dec 23
Kent Island Resort
Free daily continental breakfast
Quality Inn & Suites Bel Air I-95 Exit 77A

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

Quality Inn & Suites Bel Air I-95 Exit 77A
2.5 star property
Edgewood
7.4 out of 10, Good, (1007)
"Staff was very friendly. "
United States
Ashlee
The price is ₩87,824
₩98,365 total
includes taxes & fees
Dec 24 - Dec 25
Quality Inn & Suites Bel Air I-95 Exit 77A
Reception
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1003)
"Room was great staff friendly"
United States
Melissa
The price is ₩123,476
₩138,292 total
includes taxes & fees
Dec 27 - Dec 28
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

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

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1005)
"The room was very nice as well as the staff. The guy at the desk let us check in early which was super helpful for us! Would definitely recommend and come back to again! "
United States
Sara
The price is ₩115,490
₩129,350 total
includes taxes & fees
Dec 27 - Dec 28
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Free daily continental breakfast
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (556)
"Super clean, a great place to stay"
United States
Diana
The price is ₩121,055
₩135,582 total
includes taxes & fees
Dec 27 - Dec 28
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Very nice"
Kevin 1-night trip
Posted 4 days ago
Comfort Inn & Suites Chestertown

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 3 bars/lounges, and it's located near a private 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 Earle Landing 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.