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Our top choices for Kent County hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (909 reviews)
"Great visit"
United States
Danielle
$114 nightly
The price is $127
Jun 7 - Jun 8
Total with taxes and fees
Comfort Inn & Suites Chestertown

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (80 reviews)
"clean, comfortable, and staff was friendly and helpful. "
United States
Gail
$132 nightly
The price is $147
May 17 - May 18
Total with taxes and fees
The Lodge at Great Oak Landing

Inn at Huntingfield Creek

Inn at Huntingfield Creek
3.5 star property
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"The owners and staff were very courteous and nice. The room layout was great and thoughtfully designed and decorated."
United States
Sandra
$200 nightly
The price is $223
May 17 - May 18
Total with taxes and fees
Inn at Huntingfield Creek

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (440 reviews)
"Nothing special but good for the price. "
United States
Andreas
$71 nightly
The price is $78
May 19 - May 20
Total with taxes and fees
Red Roof Inn & Suites Chestertown

Inn at Haven Harbour

Inn at Haven Harbour
3.0 star property
Rock Hall
8.6 out of 10, Excellent, (4 reviews)
"Friendly staff at check in. This lady was helpful thru entire stay. Her name is Sharon. The Harbor had a Luau on Saturday which we attended since our son is a slip holder. Great weekend. "
United States
Gloria
Inn at Haven Harbour

Haven Point Inn and Gallery

Haven Point Inn and Gallery
2.0 star property
Rock Hall
$153 nightly
The price is $170
May 12 - May 13
Total with taxes and fees
Haven Point Inn and Gallery

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (176 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
$64 nightly
The price is $70
May 12 - May 13
Total with taxes and fees
Driftwood Inn

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
$144 nightly
The price is $159
May 12 - May 13
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (21 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
May 12 - May 13
Total with 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!

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$257 nightly
The price is $284
May 12 - May 13
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (54 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$260 nightly
The price is $276
May 12 - May 13
Total with taxes and fees
BAYSIDE BUNGALOW

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining
Rock Hall
10.0 out of 10, Exceptional, (50 reviews)
"We had an enjoyable stay at Bayside Breeze. It was a comfortable house with all the essentials. Even though the weather was cold we were toasty warm and enjoyed extra cups of tea/coffee and many games of uno and shut the box. "
United States
Christine B.
Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining

High Tide Haven Suite

High Tide Haven Suite
Kent County
10.0 out of 10, Exceptional, (2 reviews)
"The suite was really nice and extremely clean. Comfy, memory foam bed. Excellent shower with great water pressure. The ambiance in the room is serene and beachy making for a wonderful escape. Absolutely loved their screened in porch and view from the back deck. The hosts were very nice, had great communication and served the most delicious bagels. We left our phone charger there and they promptly called us in time to turn around and get it. Highly recommend this location and will stay there...
United States
Joell V.
$166 nightly
The price is $180
May 18 - May 19
Total with taxes and fees
High Tide Haven Suite

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
$372 nightly
The price is $394
Jun 2 - Jun 3
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!
Rock Hall
10.0 out of 10, Exceptional, (30 reviews)
"Beautiful home. Great little town. I would definitely stay again"
United States
Thomas
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Blue Heron Farm Waterfront Chalet

Blue Heron Farm Waterfront Chalet
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"We had an amazing stay on this picturesque slice of the Eastern Shore. The house is perfectly situated for stunning sunsets with ample outdoor space. We loved being able to cook out dinner while taking in wildlife and the water.Ben, our host, was quick to respond to questions and left a super helpful binder of suggestions. "
United States
Amy G.
Blue Heron Farm Waterfront Chalet

BEACH WITHOUT THE BUSTLE

BEACH WITHOUT THE BUSTLE
Betterton Beach
10.0 out of 10, Exceptional, (37 reviews)
"Beautiful and spotless and the most relaxing weekend I’ve/we had in quite some time . Will definitely be re booking this coming year for spring/summer get away"
United States
Mark S.
BEACH WITHOUT THE BUSTLE

3 Mi to Washington College! Updated Home w/ Patio

3 Mi to Washington College! Updated Home w/ Patio
3.0 star property
Chestertown
3 Mi to Washington College! Updated Home w/ Patio

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
$343 nightly
The price is $379
May 26 - May 27
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach

Be persuaded to experience this vintage cottage by the Sassa

Be persuaded to experience this vintage cottage by the Sassa
Galena
9.2 out of 10, Wonderful, (11 reviews)
"We had a nice stay! The house had everything we needed and was comfortable for our trip. Overall the place was in good shape and worked well for us."
United States
Kristen P.
Be persuaded to experience this vintage cottage by the Sassa
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Top Kent County Hotel Reviews

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