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Check availability on Chestertown Beach Resorts & Hotels

Tonight
29 Dec - 30 Dec
Tomorrow
30 Dec - 31 Dec
This weekend
2 Jan - 4 Jan
Next weekend
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
31 Dec - 1 Jan 2026
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, (1006)
"Room was great staff friendly"
United States
Melissa
The price is ฿2,596
฿2,907 total
includes taxes & fees
4 Jan - 5 Jan 2026
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
3.0 star property
Edgewood
8.2 out of 10, Very good, (1007)
"Quiet location, clean and convenient. "
United States
Louis J
The price is ฿2,141
฿2,398 total
includes taxes & fees
30 Dec - 31 Dec
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
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 ฿3,730
฿5,221 total
includes taxes & fees
4 Jan - 5 Jan 2026
Kent Island Resort
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, (340)
"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
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, (1013)
"Room was very nice. Staff is always very nice."
United States
Peggy
The price is ฿1,846
฿2,068 total
includes taxes & fees
30 Dec - 31 Dec
Quality Inn & Suites Bel Air I-95 Exit 77A
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, (1002)
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
The price is ฿2,458
฿2,753 total
includes taxes & fees
19 Jan - 20 Jan 2026
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Lobby
Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (304)
"Always consistent and great staff!"
United States
Linda
The price is ฿3,383
฿3,789 total
includes taxes & fees
4 Jan - 5 Jan 2026
Fairfield Inn & Suites by Marriott Aberdeen
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, (98)
"Spotless, very good "
United States
Efrain
The price is ฿3,383
฿3,789 total
includes taxes & fees
30 Dec - 31 Dec
TownePlace Suites by Marriott Edgewood Aberdeen
Terrace/patio
Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG

Holiday Inn Express Aberdeen by IHG
2.5 star property
Aberdeen
8.6 out of 10, Excellent, (430)
"Most comfortable beds and pillows. Great breakfast. Very clean. Would definitely recommend it. "
United States
Diana
The price is ฿3,259
฿3,650 total
includes taxes & fees
1 Jan - 2 Jan 2026
Holiday Inn Express Aberdeen 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.