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

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Check availability on Chestertown Beach Hotels

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
3.0 star property
Chestertown
8.0 out of 10, Very Good, (91 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 ₩197,788
₩226,130 total
includes taxes & fees
Jul 16 - Jul 17
The Lodge at Great Oak Landing
Free daily continental breakfast

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, (1,167 reviews)
The price is ₩95,306
₩106,742 total
includes taxes & fees
Jul 19 - Jul 20
Quality Inn & Suites Bel Air I-95 Exit 77A
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,012 reviews)
The price is ₩135,118
₩151,332 total
includes taxes & fees
Aug 5 - Aug 6
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior

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, (1,012 reviews)
The price is ₩163,927
₩183,599 total
includes taxes & fees
Jul 26 - Jul 27
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
3.0 star property
Bel Air
8.8 out of 10, Excellent, (1,009 reviews)
The price is ₩142,847
₩159,989 total
includes taxes & fees
Jul 19 - Jul 20
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
In-room safe, desk, iron/ironing board, free WiFi

Super 8 by Wyndham Aberdeen MD

Super 8 by Wyndham Aberdeen MD
2.0 star property
Aberdeen
6.8 out of 10, (886 reviews)
The price is ₩83,884
₩93,950 total
includes taxes & fees
Jul 21 - Jul 22
Super 8 by Wyndham Aberdeen MD
Lobby lounge

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, (882 reviews)
The price is ₩160,115
₩184,933 total
includes taxes & fees
Jul 20 - Jul 21
SpringHill Suites Baltimore White Marsh/Middle River
Indoor pool

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area

Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
3.0 star property
Edgewood
7.0 out of 10, Good, (1,012 reviews)
The price is ₩97,848
₩109,590 total
includes taxes & fees
Aug 3 - Aug 4
Wingate by Wyndham Bel Air I-95 Exit 77A / APG Area
Free daily continental breakfast

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, (618 reviews)
The price is ₩140,893
₩157,800 total
includes taxes & fees
Aug 10 - Aug 11
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Lounge

Americas Best Value Inn Edgewood

Americas Best Value Inn Edgewood
2.0 star property
Edgewood
6.0 out of 10, (1,005 reviews)
The price is ₩88,938
₩99,610 total
includes taxes & fees
Jul 16 - Jul 17
Americas Best Value Inn Edgewood
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
"Room excellent, very clean, well stocked breakfast, nice outdoor pool with lots of privacy, great restaurants walking distance"
Davis 3-night trip
Posted 18 hours 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 free WiFi, 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 Chestertown Historic District or Rolphs Wharf Marina.
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.