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Find Beach Hotels in Chestertown, MD

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Compare Chestertown Beach Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Comfort Inn & Suites Chestertown
Exterior

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (735)
"."
The price is AED 375
AED 417 total
includes taxes & fees
1 Jan - 2 January 2025
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Exterior

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (322)
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. You have to go out for breakfast. Excuse was not since Covid. That adds another $20 per couple for breakfast to the room price."
The price is AED 251
AED 279 total
includes taxes & fees
1 Jan - 2 January 2025
Red Roof Inn & Suites Chestertown
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.0 out of 10, (167)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is AED 233
AED 259 total
includes taxes & fees
27 Dec - 28 Dec
Driftwood Inn
The Lodge at Great Oak Landing
Room

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (46)
"Generally okay, Clean but property could use some upgrade"
The Lodge at Great Oak Landing
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Pool

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock

10.0 out of 10, Exceptional, (61)
"Great!"
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
First Floor Studio Apartment in Historic Chestertown
Back Yard

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (77)
"The room and bathroom were very spacious and clean! I love and appreciate the small toiletries that were left for us! The small refrigerator and table are a nice touch that we used during our stay! "
The price is AED 360
AED 579 total
includes taxes & fees
1 Jan - 2 January 2025
First Floor Studio Apartment in Historic Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
looking down river from the dock

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

9.8 out of 10, Exceptional, (80)
"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
Exterior

Beautiful, spacious waterfront home, an easy walk to historic Chestertown

9.8 out of 10, Exceptional, (22)
"Perfect spot for our whole family to be together. It has it all. Everything worked. Super comfy. Thank you!!!!"
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
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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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 free WiFi, 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 Earle Landing for some quality time by the water. Experience the area’s university life, and make time for local attractions like Washington College and Rolphs Wharf Marina. For more things to see and do, consider visiting River Arts Chestertown or Historical Society of Kent County Maryland.
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.