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Find Beach Hotels in Chestertown, MD

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Check availability on Chestertown Beach Hotels

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

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (760)
"Staff was efficient and very helpful. Clean room with microwave & fridge - well stocked linens in bathroom - great breakfast - thank you for a comfortable stay."
The price is SAR 411
SAR 457 total
includes taxes & fees
18 May - 19 May
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (349)
"Easy to get to, food all around!"
The price is SAR 257
SAR 285 total
includes taxes & fees
14 May - 15 May
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.2 out of 10, (170)
"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 264 total
includes taxes & fees
25 May - 26 May
Driftwood Inn
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
7.8 out of 10, Good, (48)
"Wonderful quiet place. Enjoyed our night."
The price is SAR 441
SAR 490 total
includes taxes & fees
11 May - 12 May
The Lodge at Great Oak Landing
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)
"We had a great time"
Beautiful, spacious waterfront home, an easy walk to historic Chestertown
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (83)
"Quiet neighborhood and the best place to stay."
The price is SAR 368
SAR 592 total
includes taxes & fees
13 May - 14 May
First Floor Studio Apartment in Historic Chestertown
Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

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
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Terrace/patio

Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!

10.0 out of 10, Exceptional, (76)
"Spacious, extremely well maintained and appointed home on the Chester River. We would definitely stay here again. "
Private Waterfront Paradise w/ Pier - Kayak to Historic Chestertown!
Country Estate in Historic District
Fridge, microwave, oven, stovetop

Country Estate in Historic District

10.0 out of 10, Exceptional, (67)
"Great stay!"
Country Estate in Historic District
Contemporary waterfront house with private dock & kayaks!
Property grounds

Contemporary waterfront house with private dock & kayaks!

10.0 out of 10, Exceptional, (65)
"We thoroughly enjoyed John and Kate's idyllic house and countryside nearby. Lovely view of Worton Creek and loads of Great Blue Herons. "
Contemporary waterfront house with private dock & kayaks!
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 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 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 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.