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Beach Resorts in Chestertown

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Check availability on Chestertown Beach Resorts

Top Beach Resorts in Chestertown

Our top choices for Chestertown beach hotels

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (797)
"It was a clean comfortable spot to rest for the night. "
The price is S$156
includes taxes & fees
7 Sept - 8 Sept
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout curtains

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (387)
"Good location."
The price is S$103
includes taxes & fees
28 Aug - 29 Aug
Red Roof Inn & Suites Chestertown
Driftwood Inn
Front of property – evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (172)
"Rooms are clean, staf was helpful "
Driftwood Inn
The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (65)
"Great place to get some quiet rest by the water"
The price is S$189
includes taxes & fees
24 Aug - 25 Aug
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.

Top Chestertown Hotel Reviews

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 .
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.