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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

2.5 star property
8.6 out of 10, Excellent, (727)
"Was there just one night and didn't eat breakfast, but staff were wonderful and the room seemed newly renovated. Room was large and clean with coffee maker and mini-fridge. "
The price is AED 391
AED 431 total
includes taxes & fees
25 Dec - 26 Dec
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (320)
"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 274
AED 301 total
includes taxes & fees
1 Dec - 2 Dec
Red Roof Inn & Suites Chestertown

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
26 Nov - 27 Nov
Driftwood Inn

The Lodge at Great Oak Landing

3.5 star property
7.6 out of 10, Good, (45)
"Generally okay, Clean but property could use some upgrade"
The price is AED 369
AED 410 total
includes taxes & fees
26 Nov - 27 Nov
The Lodge at Great Oak Landing

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

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

9.6 out of 10, Exceptional, (75)
"EasyvPeasy place."
The price is AED 360
AED 579 total
includes taxes & fees
27 Nov - 28 Nov
First Floor Studio Apartment in Historic Chestertown

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

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.