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Top Cities in Kent County

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

Chestertown

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Aug 7 - Aug 8
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Aug 8 - Aug 9
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Aug 8 - Aug 10
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Compare 2,378 hotels in Kent County with 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, (791)
"It was a clean comfortable spot to rest for the night. "
$110 nightly
The price is $122
Aug 17 - Aug 18
Total includes taxes and fees
Comfort Inn & Suites Chestertown
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, (59)
"Great place to get some quiet rest by the water"
$147 nightly
The price is $163
Aug 10 - Aug 11
Total includes taxes and fees
The Lodge at Great Oak Landing
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, (384)
"Good location."
$72 nightly
The price is $80
Aug 14 - Aug 15
Total includes taxes and fees
Red Roof Inn & Suites Chestertown
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (52)
"Everything was lovely. Our cottage private and very nice. Breakfast delicious. Close to town. "
$189 nightly
The price is $210
Aug 13 - Aug 14
Total includes taxes and fees
Inn at Huntingfield Creek
Inn at Haven Harbour
View from property

Inn at Haven Harbour

3.0 star property
10.0 out of 10, Exceptional, (2)
"We recently had the pleasure of staying at the Inn at Haven Harbour, specifically at their south location, and can't say enough good things about our experience! From the moment we arrived, we were captivated by the immaculate property and stunning surroundings. The views of the water were breathtaking, and having access to a private beach made our stay feel even more special. The amenities were top-notch, with a pool available for those who prefer a swim to the beach. The staff were incredibly...
$227 nightly
The price is $252
Aug 12 - Aug 13
Total includes taxes and fees
Inn at Haven Harbour
Driftwood Inn
Front of property - evening/night

Driftwood Inn

2.0 star property
5.2 out of 10, (171)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
$64 nightly
The price is $70
Aug 11 - Aug 12
Total includes taxes and fees
Driftwood Inn
Mariners Motel
Marina

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (89)
"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
Aug 10 - Aug 11
Total includes taxes and fees
Mariners Motel
Guest Suite for up to 2 in a Victorian on the Chester River
Exterior

Guest Suite for up to 2 in a Victorian on the Chester River

10.0 out of 10, Exceptional, (16)
"The staff was great"
$111 nightly
The price is $118
Aug 12 - Aug 13
Total includes taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (10)
"Perfection"
$265 nightly
The price is $293
Aug 12 - Aug 13
Total includes taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (93)
"Very pretty location. Few minutes drive to town center."
$144 nightly
The price is $159
Aug 13 - Aug 14
Total includes taxes and fees
First Floor Studio Apartment in Historic Chestertown
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (43)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
$282 nightly
The price is $299
Aug 10 - Aug 11
Total includes taxes and fees
BAYSIDE BUNGALOW
Waterfront Retreat with Private Dock and Beach
Beach

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (22)
"Everything was lovely! The dock was beautiful and the accommodations were comfortable.Thanks!"
$341 nightly
The price is $376
Aug 11 - Aug 12
Total includes taxes and fees
Waterfront Retreat with Private Dock and Beach
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio

Grandma’s Cottage will wrap around you like a warm hug

$395 nightly
The price is $419
Aug 11 - Aug 12
Total includes taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Knot's Landing, spacious Apt. downtown Rock Hall
Property grounds

Knot's Landing, spacious Apt. downtown Rock Hall

9.0 out of 10, Wonderful, (4)
"This property is near many of the downtown places you want to visit, and all are within walking distance. "
Knot's Landing, spacious Apt. downtown Rock Hall
Cute waterfront apartment -- 8 min from the beach!
Outdoor dining

Cute waterfront apartment -- 8 min from the beach!

10.0 out of 10, Exceptional, (6)
"Nice and quiet with a great location and amazing view!!!"
Cute waterfront apartment -- 8 min from the beach!
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Beach towels

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

9.8 out of 10, Exceptional, (61)
"It’s a nice place"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (115)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food
Charming cottage with Pool Access and WiFi in lovely Rock Hall
Outdoor pool

Charming cottage with Pool Access and WiFi in lovely Rock Hall

Charming cottage with Pool Access and WiFi in lovely Rock Hall
River Cottage, Chestertown
Fridge, microwave, oven, stovetop

River Cottage, Chestertown

2.0 star property
8.0 out of 10, Very Good, (1)
"Location is very quiet and tranquil. "
River Cottage, Chestertown
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (37)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
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

Bally's Dover Casino Resort

Bally's Dover Casino Resort

10/10 Excellent
"A"
Craig 1-night trip
Posted 15 hours ago
Bally's Dover Casino Resort