Beach Hotels in Chestertown, Maryland

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Check availability on Chestertown Beach Hotels

Top Chestertown Beach Hotels

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Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
  • Seasonal outdoor pool
8.6 out of 10, Excellent, (847)
The price is P6,024
P6,686 total
includes taxes & fees
Nov 19 - Nov 20
Comfort Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Laundry
  • Housekeeping
7.2 out of 10, Good, (416)
The price is P4,252
P4,720 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
Chestertown
  • Pet friendly
  • Parking included
  • Free WiFi
  • Air conditioning
  • Housekeeping
  • 24/7 front desk
5.2 out of 10, (175)
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
Chestertown
  • Private beach access
  • Beach loungers
  • Seasonal outdoor pool
8.0 out of 10, Very Good, (75)
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 P5,846
P6,684 total
includes taxes & fees
Nov 17 - Nov 18
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
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
Santa 5-night trip
Posted 2 days ago
Comfort Inn & Suites Chestertown

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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 Historical Society of Kent County Maryland. 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.