An aerial view of a town with a river, buildings, and surrounding greenery.

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Check availability on Chestertown Beach Hotels

This weekend
Oct 30 - Nov 1
Next weekend
Nov 6 - Nov 8

Our top choices for Chestertown beach hotels

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

1. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (124 reviews)
  • cleanliness
    Escape to waterfront tranquility with a private beach just 0.25 miles away, where sandy shores, volleyball courts, and loungers await.
The price is ￥16,942
￥19,370 total
includes taxes & fees
Oct 27 - Oct 28
The Lodge at Great Oak Landing
A modern hotel lobby with a long dining table, several chairs, and a bar area.

2. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,006 reviews)
The price is ￥13,378
￥14,984 total
includes taxes & fees
Nov 1 - Nov 2
Hampton Inn & Suites Edgewood/Aberdeen-South
A hotel lobby with multiple seating areas, a coffee station, and a kitchen in the background.

3. 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, (1,229 reviews)
The price is ￥10,091
￥11,302 total
includes taxes & fees
Nov 11 - Nov 12
Quality Inn & Suites Bel Air I-95 Exit 77A
A hotel entrance with a clear sign reading "LA QUINTA".

4. City Express by Marriott Aberdeen

City Express by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,005 reviews)
The price is ￥14,903
￥16,691 total
includes taxes & fees
Oct 29 - Oct 30
City Express by Marriott Aberdeen
A buffet area with multiple self-service stations, including trays of omelets and other prepared foods.

5. 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, (660 reviews)
The price is ￥13,805
￥15,462 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

6. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (968 reviews)
The price is ￥16,801
￥19,405 total
includes taxes & fees
Nov 1 - Nov 2
SpringHill Suites Baltimore White Marsh/Middle River
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

7. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (312 reviews)
The price is ￥16,534
￥18,518 total
includes taxes & fees
Nov 1 - Nov 2
Hilton Garden Inn Bel Air
A spacious living area with a staircase, a fireplace, a sofa, and a dining area.

8. 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, (1,007 reviews)
The price is ￥13,977
￥15,653 total
includes taxes & fees
Nov 1 - Nov 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.

9. 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, (430 reviews)
The price is ￥15,307
￥17,145 total
includes taxes & fees
Nov 22 - Nov 23
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A hotel with a prominent sign, multiple parking spaces, and a covered entrance.

10. 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, (1,140 reviews)
The price is ￥12,448
￥13,941 total
includes taxes & fees
Nov 24 - Nov 25
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
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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Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Good hotel"
Michael 1-night trip
Posted 2 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 2 restaurants and a seasonal outdoor pool, and it's located near a private beach. Great Oak Manor is another good option to stay near the 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 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.