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Beach Hotels in Chestertown, Maryland

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Check availability on Chestertown Beach Hotels

Top 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 P6,248
P6,935 total
includes taxes & fees
Sep 7 - Sep 8
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (387)
"Good location."
The price is P4,103
P4,554 total
includes taxes & fees
Aug 28 - Aug 29
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 P7,539
P8,368 total
includes taxes & fees
Aug 24 - Aug 25
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

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

10/10 Excellent
"FEELS LIKE PEACEFULLY 👍 👌 "
Brian 4-night trip
Posted 7 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.