An aerial view of a town with a river, buildings, and surrounding greenery.

Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Our top choices for Chestertown beach hotels

A hotel lobby with a fireplace, seating area, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (1,000 reviews)
"The front desk staff were so nice, room very clean."
United States
John
The price is ₩129,714
₩143,983 total
includes taxes & fees
Dec 6 - Dec 7
Comfort Inn & Suites Chestertown
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (513 reviews)
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed. The room needs up dating since damage area on ceiling and corner location rug worn spot. I felt safe as a solo, could check in late and close to historic Chestertown. I would come again."
United States
Regina
The price is ₩96,695
₩107,331 total
includes taxes & fees
Nov 25 - Nov 26
Red Roof Inn & Suites Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (129 reviews)
"Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area."
United States
William
The price is ₩145,060
₩165,847 total
includes taxes & fees
Nov 12 - Nov 13
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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Choose what matters most at beach hotels in Chestertown

Pool
Breakfast included

Top Chestertown Hotel Reviews

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

8/10 Good
"Coffee in the breakfast area was terrible. Weak and watery. Thta' might seem like a minor factor. but for those of us who appreciate a good, strong cup of coffee, it's a problem."
Richard 1-night trip
Posted 2 days ago
Hilton Garden Inn Kent Island Marina
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

8/10 Good
"Convenient location, friendly staff, clean"
Ann Marie 2-night trip
Posted 3 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 2 restaurants and a seasonal outdoor pool, and it's located near a private beach. Great Oak Manor is another good option to stay near the 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 Chestertown Historic District.
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.