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Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Tonight
Nov 3 - Nov 4
Tomorrow
Nov 4 - Nov 5
This weekend
Nov 7 - Nov 9
Next weekend
Nov 14 - Nov 16

Top Chestertown Beach Hotels

Lobby
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
  • Seasonal outdoor pool
8.6 out of 10, Excellent, (838)
The price is ₩145,820
₩161,860 total
includes taxes & fees
Nov 5 - Nov 6
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
  • Housekeeping
7.2 out of 10, Good, (409)
The price is ₩102,932
₩114,255 total
includes taxes & fees
Nov 30 - Dec 1
Red Roof Inn & Suites Chestertown
Front of property - evening/night
Driftwood Inn
Driftwood Inn
2.0 star property
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
5.2 out of 10, (174)
Driftwood Inn
Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing
The Lodge at Great Oak Landing
3.5 star property
  • Private beach access
  • Beach loungers
  • Seasonal outdoor pool
8.0 out of 10, Very Good, (73)
This waterfront lodge provides a beach paradise with complimentary loungers on sandy shores. After beach volleyball games, guests can retreat to air-conditioned rooms, gather around the firepit, or enjoy meals at the restaurant with drinks from three bars.
The price is ₩141,531
₩161,813 total
includes taxes & fees
Nov 4 - Nov 5
The Lodge at Great Oak Landing
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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Top Chestertown Hotel Reviews

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"Everything was great - the beds and pillows are very comfortable, room very clean and breakfast was decent and staff very friendly. "
Charles 1-night trip
Posted 13 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 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 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.