Find Beach Hotels in Chestertown, MD

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Beach Hotels

Tonight
Jan 2 - Jan 3
Tomorrow
Jan 3 - Jan 4
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

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 ￥15,517
￥17,741 total
includes taxes & fees
Jan 4 - Jan 5
The Lodge at Great Oak Landing
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, (1000)
"Quiet location, clean and convenient. "
United States
Louis J
The price is ￥11,058
￥12,384 total
includes taxes & fees
Jan 11 - Jan 12
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
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, (1011)
"Awesome 2 night stay will be back❤️❤️"
United States
LaShawn
The price is ￥12,724
￥14,252 total
includes taxes & fees
Jan 7 - Jan 8
Hampton Inn & Suites Edgewood/Aberdeen-South
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 ￥18,839
￥26,367 total
includes taxes & fees
Jan 4 - Jan 5
Kent Island Resort
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, (1018)
"Room was very nice. Staff is always very nice."
United States
Peggy
The price is ￥9,324
￥10,442 total
includes taxes & fees
Jan 3 - Jan 4
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, (1004)
"We found the overall hotel and surrounding area very nice. "
United States
Jacquelyn
The price is ￥12,391
￥13,879 total
includes taxes & fees
Jan 23 - Jan 24
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Exterior
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, (475)
"The staff is great, roon clean & spacious"
United States
Thomas
The price is ￥12,985
￥14,543 total
includes taxes & fees
Jan 22 - Jan 23
Candlewood Suites Aberdeen-Bel Air by IHG
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 ￥16,458
￥18,434 total
includes taxes & fees
Jan 9 - Jan 10
Holiday Inn Express Aberdeen by IHG
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, (100)
"Clean rooms and facilities "
Canada
Fernando
The price is ￥15,854
￥17,758 total
includes taxes & fees
Jan 7 - Jan 8
TownePlace Suites by Marriott Edgewood Aberdeen
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 ￥13,984
￥15,662 total
includes taxes & fees
Jan 30 - Jan 31
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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.
View all properties

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Very nice"
Kevin 1-night trip
Posted 3 weeks 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 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.