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Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

Top Chestertown Beach Hotels

Comfort Inn & Suites Chestertown
Welcome to our reception area, where friendly staff are available to assist with your stay.

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (783)
"Great stay. Sorry pool was closed "
Anita
The price is NT$3,274
NT$3,635 total
includes taxes & fees
Aug 17 - Aug 18
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Classic hotel room with a large bed, bedside tables, and a comfortable armchair.

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (375)
"good price, convenient. pool was closed which was disappointing."
charlene
The price is NT$2,013
NT$2,234 total
includes taxes & fees
Jul 24 - Jul 25
Red Roof Inn & Suites Chestertown
Driftwood Inn
Rows of rooms with stone facades and windows line the building's side.

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
Quiana
The price is NT$1,868
NT$2,074 total
includes taxes & fees
Jul 30 - Jul 31
Driftwood Inn
The Lodge at Great Oak Landing
Surrounded by a tranquil lake, this serene setting features a cozy fire pit amidst a picturesque landscape.

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (55)
"The room was very clean and comfortable. No frills but perfect for our overnight stay. The view from the queen bed room was lovely. The waitress at the restaurant was exceptional and the food was delicious and hot. We enjoyed the private
beach
and the areas to walk around the marina."
Anonymous traveler
The price is NT$3,892
NT$4,320 total
includes taxes & fees
Jul 31 - Aug 1
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.

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.
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 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.