Photo by Assya A

Beach Resorts in Chestertown

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Check availability on Chestertown Beach Resorts

Tonight
25 Jun - 26 Jun
Tomorrow
26 Jun - 27 Jun
This weekend
27 Jun - 29 Jun
Next weekend
4 Jul - 6 Jul

Top Beach Resorts in Chestertown

The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (52)
"not super fancy but really well done. comfy beds and a first rate chef. plus great for the boating crowd"
The price is S$188
includes taxes & fees
9 Jul - 10 Jul
The Lodge at Great Oak Landing
Second Floor East Standard Deluxe
Outdoor pool

Second Floor East Standard Deluxe

2.0 star property
Second Floor East Standard Deluxe
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
Indoor pool, outdoor pool

Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!

2.0 star property
8.0 out of 10, Very good, (2)
"Nice cabin"
Amazing Getaway: Enjoy our Cozy Log Cabins on the Chesapeake Bay!
Top Floor Standard Deluxe
Outdoor pool

Top Floor Standard Deluxe

2.5 star property
10.0 out of 10, Exceptional, (1)
"Very relaxing and peaceful love it can’t wait to be there again….."
Top Floor Standard Deluxe
Top Floor Family Deluxe Bay View
Outdoor pool

Top Floor Family Deluxe Bay View

2.5 star property
Top Floor Family Deluxe Bay View
Top Floor Standard Deluxe
Outdoor pool

Top Floor Standard Deluxe

2.0 star property
Top Floor Standard Deluxe
First Floor Standard Deluxe King
Indoor pool, outdoor pool

First Floor Standard Deluxe King

2.5 star property
First Floor Standard Deluxe King
Second East Family Deluxe
Outdoor pool

Second East Family Deluxe

2.5 star property
Second East Family Deluxe
Top Floor East Handicap Accessible
Outdoor pool

Top Floor East Handicap Accessible

2.0 star property
Top Floor East Handicap Accessible
Top Floor Standard Suite
Outdoor pool

Top Floor Standard Suite

2.0 star property
Top Floor Standard Suite
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.

Frequently asked questions

What is Chestertown like for travellers who love the beach?
Known for its university life, Chestertown offers a lot for the traveller planning a getaway.
What's the best place to stay for a beach holiday 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 .
How many beach hotels are there in Chestertown?
Expedia has 6 beach hotels in Chestertown that are great for your beachside getaway.
When's the best time for a beach holiday in Chestertown?
You can plan your beach trip with this snapshot of year-round temperatures in Chestertown: The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
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 such as 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 centre. If you'd like to venture out around the area, you may want to rent a car for your trip.