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Find beach hotels & resorts in Kent County

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Top Cities in Kent County

Somewhere over the rainbow... Terrific view on the plane back to the North.
HotelsHotels

Chestertown

Chestertown

We found 54 beach stays in Kent County, from luxury resorts to beachfront rentals. Explore these popular Kent County beach destinations.

Check availability on Kent County Beach Hotels

Pick from 54 Kent County Beach Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Our top choices for Kent County beach hotels

Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (90)
"Very nice old school motel just about on the water in Rock Hall. Perfect if you’re in town for marina stuff. "
$155 nightly
The price is $172
Sep 17 - Sep 18
Total with taxes and fees
Mariners Motel
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (816)
"Friendly staff, clean room, convenient location. "
$116 nightly
The price is $129
Sep 28 - Sep 29
Total with taxes and fees
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (395)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
$76 nightly
The price is $85
Sep 23 - Sep 24
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (174)
"Rooms are clean, staf was helpful "
$64 nightly
The price is $70
Oct 14 - Oct 15
Total with taxes and fees
Driftwood Inn
Inn at Huntingfield Creek
Property grounds

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (53)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
$178 nightly
The price is $198
Sep 29 - Sep 30
Total with taxes and fees
Inn at Huntingfield Creek
Inn at Haven Harbour
On the beach, white sand, beach bar

Inn at Haven Harbour

3.0 star property
8.0 out of 10, Very Good, (3)
"Steps to the 3rd floor attic Low headroom every where 4' to 5' headroom in front of the toilet 8 yr old banged his head Everything was good except the very small room Don't rent this room unless you're 4' tall I'm surprised it passed inspection "
$179 nightly
The price is $199
Sep 25 - Sep 26
Total with taxes and fees
Inn at Haven Harbour
The Lodge at Great Oak Landing
Private beach nearby, sun loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very Good, (68)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
$118 nightly
The price is $131
Sep 18 - Sep 19
Total with taxes and fees
The Lodge at Great Oak Landing
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (48)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
$282 nightly
The price is $299
Sep 17 - Sep 18
Total with taxes and fees
BAYSIDE BUNGALOW
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun loungers, beach towels

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (44)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (100)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
$144 nightly
The price is $159
Sep 22 - Sep 23
Total with taxes and fees
First Floor Studio Apartment in 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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Top Kent County Hotel Reviews

Pier 5 Hotel Baltimore

Pier 5 Hotel Baltimore

10/10 Excellent
"Tico was very friendly and accomodating at the front desk upon check-in. He suggested lots of places to visit and restaurants to eat. He was kind enough to upgrade us to a suite with a nice view of the harbor as well. He is a wonderful asset to your hotel!!"
James 1-night trip
Posted 1 day ago
Pier 5 Hotel Baltimore

Find out more about Kent County

Find out more about Kent County

Book your dream Kent County beach vacation with deals from $70

Make the most of your vacation with hotels on the water in Kent County

How do I find the best Kent County beach hotels? 

With 1,784 unfiltered, genuine customer reviews of hotels in Kent County on the beach, you can read what people really think about their stay and get a feel for where would be perfect for you.  

 

How can I find Kent County hotels on the beach with nice views?  

From beachfront getaways overlooking a pretty pool or tranquil garden to luxury cliff-top hotels with dramatic ocean vistas, there are loads of stunning rooms with a perfect view. Use our ocean view filter for Kent County beach hotels with dreamy water views from your window.    

 

How much do Kent County beach hotels cost?  

Prices for beachfront hotels in Kent County currently start at $70 a night going up to $299 for top-notch accommodation. Prices and availability are subject to change. Additional terms may apply. 

 

How do I find family-friendly Kent County hotels on the beach? 

Use the family friendly filter to explore truly welcoming hotels offering kid-friendly amenities and fun-filled activities—from highchairs and cribs to water sports and beach games. 

 

Can I cancel my Kent County beach hotel? 

It’s easy to cancel a booking, yes. Just log into your My Trips page and go to your itinerary to see your cancellation options. If you want peace of mind knowing you can cancel, penalty-free, book one of the many beach hotels in Kent County offering free cancellation. 

 

Why should I book my Kent County beach hotel with Expedia? 

Get amazing deals on an exciting selection of hotels on the beach in Kent County, enjoy 24/7 customer service, and save more when you bundle your hotel, car rental, and flights together. With everything you need in one place, it’s easy to click, book, and travel with Expedia.   

 

Are there any Kent County beach hotels with a pool? 

Many condos, motels, hotels, and beach resorts in Kent County have a pool for you to dip into. To find them really easily, use our pool search filter.    

 

Are there any cheap Kent County beach hotels? 

Currently, there are 54 tempting beach hotels in Kent County to choose from, with prices from just $70 a night. So, compare prices, amenities, and ratings in one place for a great wallet-friendly hotel.  

Explore a world of travel with Expedia

Explore a world of travel with Expedia