Search Beach Resorts & Hotels in Chestertown

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Beach Resorts & Hotels

Tonight
30 Nov - 1 Dec
Tomorrow
1 Dec - 2 Dec
Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec

Top Chestertown Beach Resorts & Hotels

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
  • Seasonal outdoor pool
8.6 out of 10, Excellent, (857)
The price is 2.689.230 ₫
2.985.046 ₫ total
includes taxes & fees
4 Dec - 5 Dec
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board
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, (417)
The price is 1.898.280 ₫
2.107.091 ₫ total
includes taxes & fees
7 Dec - 8 Dec
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)
The price is 1.674.178 ₫
1.858.469 ₫ total
includes taxes & fees
24 Dec - 25 Dec
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, (76)
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 2.610.135 ₫
2.984.168 ₫ total
includes taxes & fees
1 Dec - 2 Dec
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.
View all properties

Top Chestertown Hotel Reviews

Explore a world of travel with Expedia

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.
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 Earle Landing for some quality time by the water. Experience the area's university life, and make time for local attractions such as 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 centre. If you'd like to venture out around the area, you may want to rent a car for your trip.