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Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Tonight
Aug 18 - Aug 19
Tomorrow
Aug 19 - Aug 20
This weekend
Aug 21 - Aug 23
Next weekend
Aug 28 - Aug 30

Our top choices for Chestertown beach hotels

1. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
  • Escape to waterfront tranquility with a private beach just 0.25 miles away, where sandy shores, volleyball courts, and loungers await.
NT$3,439
NT$3,931 total
includes taxes & fees
Aug 19 - Aug 20
The Lodge at Great Oak Landing

2. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
NT$3,107
NT$3,480 total
includes taxes & fees
Sep 7 - Sep 8
Home2 Suites by Hilton Baltimore / Aberdeen, MD

3. Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Edgewood
NT$2,802
NT$3,138 total
includes taxes & fees
Sep 1 - Sep 2
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

4. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
NT$2,663
NT$2,983 total
includes taxes & fees
Sep 6 - Sep 7
Hampton Inn & Suites Edgewood/Aberdeen-South

5. Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD
Bel Air
NT$2,845
NT$3,187 total
includes taxes & fees
Sep 7 - Sep 8
Country Inn & Suites by Radisson, Bel Air/Aberdeen, MD

6. Ramada Hotel & Conference Center by Wyndham Edgewood

Ramada Hotel & Conference Center by Wyndham Edgewood
Edgewood
NT$2,746
NT$3,076 total
includes taxes & fees
Aug 19 - Aug 20
Ramada Hotel & Conference Center by Wyndham Edgewood

7. La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Edgewood
NT$2,388
NT$2,674 total
includes taxes & fees
Sep 7 - Sep 8
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8. Super 8 by Wyndham Havre De Grace Aberdeen Area

Super 8 by Wyndham Havre De Grace Aberdeen Area
Havre De Grace
NT$1,816
NT$2,034 total
includes taxes & fees
Sep 6 - Sep 7
Super 8 by Wyndham Havre De Grace Aberdeen Area
View all properties

Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included
4 stars
5 stars
All-inclusive

Top Chestertown Hotel Reviews

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

8/10 Good
"The property needs updating"
Brandon 3-night trip
Posted 1 day ago
Best Western Kent Narrows Inn
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"The door into the building from the parking lot is always locked, which is great, because it cannot be seen from the front desk, but it is difficult to enter with the room key. The key is a typical credit card-like key, but the electronic reader was wonky. Sometimes it worked and sometimes it didn’t. The cards worked well on the room doors but not on the entrance door. It was an inconvenience to walk around the building to get it the main entrance if the card did not work."
Mary Ellen 2-night trip
Posted 4 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 free WiFi, 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 Chestertown Historic District. For more things to see and do, consider visiting Northern Chesapeake Bay or 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.

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