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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
3.5 star property
Chestertown
7.8 out of 10, Good, (77 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 ￥16,979
￥19,412 total
includes taxes & fees
Mar 1 - Mar 2
The Lodge at Great Oak Landing
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,011 reviews)
The price is ￥12,763
￥14,293 total
includes taxes & fees
Feb 15 - Feb 16
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (1,001 reviews)
The price is ￥12,452
￥13,946 total
includes taxes & fees
Mar 1 - Mar 2
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
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, (1,002 reviews)
The price is ￥13,364
￥14,968 total
includes taxes & fees
Feb 17 - Feb 18
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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, (1,049 reviews)
The price is ￥8,724
￥9,772 total
includes taxes & fees
Feb 10 - Feb 11
Quality Inn & Suites Bel Air I-95 Exit 77A
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, (570 reviews)
The price is ￥12,892
￥14,439 total
includes taxes & fees
Feb 27 - Feb 28
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (310 reviews)
The price is ￥17,212
￥19,278 total
includes taxes & fees
Feb 10 - Feb 11
Fairfield Inn & Suites by Marriott Aberdeen
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (132 reviews)
The price is ￥17,010
￥24,279 total
includes taxes & fees
Feb 10 - Feb 11
Kent Island Resort
Terrace/patio

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, (346 reviews)
The price is ￥14,697
￥16,461 total
includes taxes & fees
Feb 19 - Feb 20
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Front of property - evening/night

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (435 reviews)
The price is ￥24,518
￥31,215 total
includes taxes & fees
Feb 10 - Feb 11
The Inn at Chesapeake Bay Beach Club
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
Ocean view

Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Polite and kind hotel manager"
Richard 1-night trip
Posted 2 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 Earle Landing for some quality time by the water. Experience the area's university life, and make time for local attractions like Washington College and Northern Chesapeake Bay. For more things to see and do, consider visiting Chesapeake Bay or River Arts Chestertown.
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.