Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Tonight
Dec 25 - Dec 26
Tomorrow
Dec 26 - Dec 27
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

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 ￥15,438
￥17,651 total
includes taxes & fees
Dec 28 - Dec 29
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, (1001)
"Room was great staff friendly"
United States
Melissa
The price is ￥13,043
￥14,607 total
includes taxes & fees
Jan 2 - Jan 3, 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, (338)
"Ty"
United States
Mary
The price is ￥11,139
￥12,475 total
includes taxes & fees
Jan 10 - Jan 11, 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, (95)
"Spotless, very good "
United States
Efrain
The price is ￥16,997
￥19,035 total
includes taxes & fees
Dec 27 - Dec 28
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 ￥18,636
￥26,108 total
includes taxes & fees
Dec 28 - Dec 29
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, (1000)
"Nice place"
United States
Maria
The price is ￥13,918
￥15,588 total
includes taxes & fees
Jan 4 - Jan 5, 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, (1003)
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
The price is ￥12,350
￥13,832 total
includes taxes & fees
Jan 20 - Jan 21, 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, (1009)
"Room was very nice. Staff is always very nice."
United States
Peggy
The price is ￥9,277
￥10,390 total
includes taxes & fees
Dec 28 - Dec 29
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, (233)
"Wonderful staff! So nice, clean and comfortable. Will definitely stay there again."
United States
Melissa
The price is ￥15,217
￥17,043 total
includes taxes & fees
Jan 23 - Jan 24, 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 ￥12,943
￥14,495 total
includes taxes & fees
Jan 6 - Jan 7, 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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Very nice"
Kevin 1-night trip
Posted 11 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 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 Crumpton Auction.
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.