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Check availability on Chestertown Beach Resorts & Hotels

Tonight
27 Dec - 28 Dec
Tomorrow
28 Dec - 29 Dec
Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan

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 ฿3,072
฿3,513 total
includes taxes & fees
29 Dec - 30 Dec
The Lodge at Great Oak Landing
Restaurant
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, (1004)
"Room was great staff friendly"
United States
Melissa
The price is ฿2,596
฿2,907 total
includes taxes & fees
2 Jan - 3 Jan 2026
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (339)
"Clean room, friendly staff"
United States
Julie
The price is ฿2,214
฿2,480 total
includes taxes & fees
10 Jan - 11 Jan 2026
Home2 Suites by Hilton Baltimore / Aberdeen, MD
View from property
TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (97)
"Spotless, very good "
United States
Efrain
The price is ฿3,383
฿3,789 total
includes taxes & fees
28 Dec - 29 Dec
TownePlace Suites by Marriott Edgewood Aberdeen
Aerial view
Kent Island Resort

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (130)
"Beautiful and peaceful property!"
United States
Jerry
The price is ฿3,699
฿5,184 total
includes taxes & fees
28 Dec - 29 Dec
Kent Island Resort
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, (1002)
"Nice place"
United States
Maria
The price is ฿2,770
฿3,102 total
includes taxes & fees
4 Jan - 5 Jan 2026
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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, (1001)
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
The price is ฿2,458
฿2,753 total
includes taxes & fees
17 Jan - 18 Jan 2026
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Desk, free WiFi, bed sheets, alarm clocks
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, (1010)
"Room was very nice. Staff is always very nice."
United States
Peggy
The price is ฿1,846
฿2,068 total
includes taxes & fees
28 Dec - 29 Dec
Quality Inn & Suites Bel Air I-95 Exit 77A
Reception
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, (234)
"Wonderful staff! So nice, clean and comfortable. Will definitely stay there again."
United States
Melissa
The price is ฿3,028
฿3,392 total
includes taxes & fees
9 Jan - 10 Jan 2026
Hilton Garden Inn Bel Air
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, (562)
"This is my forth time at this hotel. Excellent service . Not staying for breakfast but usually very good"
United States
Carolyn
The price is ฿2,576
฿2,885 total
includes taxes & fees
6 Jan - 7 Jan 2026
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

Frequently asked questions

What is Chestertown like for travellers who love the beach?
Known for its university life, Chestertown offers a lot for the traveller planning a getaway.
What's the best place to stay for a beach holiday 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 holiday in Chestertown?
You can plan your beach trip with this snapshot of year-round temperatures in Chestertown: The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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 such as Washington College and River Arts Chestertown. For more things to see and do, consider visiting Historical Society of Kent County Maryland 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 centre. If you'd like to venture out around the area, you may want to rent a car for your trip.