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Find beach hotels & resorts in Kent County

Beach vacation deals from $80

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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 59 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 59 Kent County Beach Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Marina
Mariners Motel

Mariners Motel

2.0 star property
Rock Hall
9.4 out of 10, Exceptional, (90)
"Location was great, near marinas, very nautical atmosphere, old world charm"
United States
Christopher
$144 nightly
The price is $160
Nov 12 - Nov 13
Total with taxes and fees
Mariners Motel
Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (844)
"This property is clean and welcoming. We were pleasantly surprised. Check in was easy, and the room was great. Breakfast was wonderful! Great place to stay."
United States
Paula
$102 nightly
The price is $113
Nov 16 - Nov 17
Total with taxes and fees
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (414)
"This property was clean but dated. The carpet was stained, the furniture and fixtures were worn and broken, towels were washed but old and in need of replacement."
United States
Derek
$72 nightly
The price is $80
Nov 30 - Dec 1
Total with taxes and fees
Red Roof Inn & Suites Chestertown
Front of property - evening/night
Driftwood Inn

Driftwood Inn

2.0 star property
Chestertown
5.2 out of 10, (174)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
United States
Quiana
Driftwood Inn
Property grounds
Inn at Huntingfield Creek

Inn at Huntingfield Creek

3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (56)
"Wonderful! Quiet and relaxing anniversary! Pool was great, dock is beautiful, room was clean, comfortable and spacious. Water bottles and cookies are such a nice touch. Breakfast was delicious. Amazing property and genuine hosts. Thank you"
United States
Cristy
$144 nightly
The price is $160
Dec 1 - Dec 2
Total with taxes and fees
Inn at Huntingfield Creek
Private beach nearby, sun loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

3.5 star property
Chestertown
8.0 out of 10, Very Good, (75)
"Very nice rooms, "
United States
Stephania
$113 nightly
The price is $126
Nov 12 - Nov 13
Total with taxes and fees
The Lodge at Great Oak Landing
On the beach, white sand, beach bar
Inn at Haven Harbour

Inn at Haven Harbour

3.0 star property
Rock Hall
8.6 out of 10, Excellent, (4)
"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 "
United States
Wayne
Inn at Haven Harbour
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"We enjoyed another great weekend at one of our favorite spots. Such a cute cottage with everything you need. So lovely to sit on the porch and enjoy the beautiful views and gardens. We have a return visit already planned."
United States
Scott Z.
BAYSIDE BUNGALOW
Marina
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

Rock Hall
9.8 out of 10, Exceptional, (66)
"Very well kept cottage. Its location is ideal for walking to restaurants on the water. We enjoyed the back porch with birds singing and shade from the large oak trees. A large bath was a nice feature/"
United States
David G.
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (105)
"Wonderful stay in a beautiful location convenient to everything. Host was outstanding."
United States
Randy B.
$144 nightly
The price is $159
Nov 12 - Nov 13
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

Lord Baltimore Hotel

Lord Baltimore Hotel

10/10 Excellent
"I did not eat breakfast"
Jazmin 1-night trip
Posted 18 hours ago
Lord Baltimore Hotel

Find out more about Kent County

Book your dream Kent County beach vacation with deals from $80

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 1,859 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 $80 a night going up to $160 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 59 tempting beach hotels in Kent County to choose from, with prices from just $80 a night. So, compare prices, amenities, and ratings in one place for a great wallet-friendly hotel.  

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