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Find Beach Hotels in Chestertown, MD

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Pick from 11 Chestertown Beach Hotels and compare 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, (723)
"Very clean and comfortable home away from home, and breakfast in the morning, too. Perfect place to stay to enjoy the Sultana Downrigging Festival, just a short drive away. And, Chestertown is a beautiful and friendly town, too!"
The price is SAR 401
SAR 442 total
includes taxes & fees
2 Dec - 3 Dec
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Exterior
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (314)
"A little rough around the edges in some ways, but the rooms were large, quiet, and clean. "
The price is SAR 297
SAR 326 total
includes taxes & fees
1 Dec - 2 Dec
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 SAR 238
SAR 265 total
includes taxes & fees
6 Nov - 7 Nov
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, (44)
"Generally okay, Clean but property could use some upgrade"
The price is SAR 377
SAR 415 total
includes taxes & fees
12 Nov - 13 Nov
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
Eastern Shore Hideaway with Grill, Kayaks & Wkend Access Dive Bar & Restaurants
Shanty Beach Bar Open Memorial Day - Labor Day
Eastern Shore Hideaway with Grill, Kayaks & Wkend Access Dive Bar & Restaurants
10.0 out of 10, Exceptional, (12)
"The Tolchester house is a lovely house with five nice bedrooms, a large back deck, a very easy to work in kitchen and a garage full of games. It is with in walking distance of the beach, marina and Shanty bar which really provides as much entertainment as you can ask for. We did go to “Pirates and Wenches” weekend in nearby Rock Hall which was great fun. We used the house as an overflow option for my family and it worked very well."
Eastern Shore Hideaway with Grill, Kayaks & Wkend Access Dive Bar & Restaurants
First Floor Studio Apartment in Historic Chestertown
Back Yard
First Floor Studio Apartment in Historic Chestertown
9.6 out of 10, Exceptional, (71)
"Just what we needed for the night! Thank you "
The price is SAR 368
SAR 569 total
includes taxes & fees
13 Nov - 14 Nov
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, (79)
"House was even better than the photos showed. We spent evenings out on the dock watvhing the river and beautiful views. The hosts thought of every detail for a perfect stay."
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.
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 River Arts Chestertown. For more things to see and do, consider visiting Rolphs Wharf Marina 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.