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Top Cities in Kent County

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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, (859)
"The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. "
United States
Santa
The price is €97
includes taxes & fees
11 Jan - 12 Jan 2026
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (420)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is €68
includes taxes & fees
18 Dec - 19 Dec
Red Roof 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, (77)
"Very nice rooms, "
United States
Stephania
The price is €96
includes taxes & fees
15 Dec - 16 Dec
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, (58)
"We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!"
United States
Aaron
Inn at Huntingfield Creek

Inn at Haven Harbour

Inn at Haven Harbour
3.0 star property
Rock Hall
8.6 out of 10, Excellent, (4)
"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

Mariners Motel

Mariners Motel
2.0 star property
Rock Hall
9.4 out of 10, Exceptional, (90)
"Although I booked this thinking it was a different place, lol it was a VERY nice and clean, peaceful, convenient retreat. It was actually a better choice than my original selection, You can walk to most things in town and the cleanliness, and charm and quiet were just what I needed to relax. "
United States
Michael
Mariners Motel

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is €139
includes taxes & fees
22 Dec - 23 Dec
First Floor Studio Apartment in Historic Chestertown

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (175)
"Rooms are clean, staf was helpful "
United States
Daryl
Driftwood Inn

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
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is €110
includes taxes & fees
12 Jan - 13 Jan 2026
Guest Suite for up to 2 in a Victorian on the Chester River

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is €264
includes taxes & fees
1 Jan - 2 Jan 2026
BAYSIDE BUNGALOW

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, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is €266
includes taxes & fees
11 Jan - 12 Jan 2026
Waterfront Retreat with Private Dock and Beach

Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants
2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
Chesapeake Bay Harbor View in a central location to events/restaurants

High Tide Haven Suite

High Tide Haven Suite
Kent County
The price is €176
includes taxes & fees
26 Dec - 27 Dec
High Tide Haven Suite

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!
Chestertown
10.0 out of 10, Exceptional, (12)
"Great cabin and the dock is amazing. Family and dog had a lot of fun and it was convenient for visiting beaches and parks. "
United States
Marnie D.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

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, (29)
"I've stayed at many bnbs and this one felt the most luxurious/resort-like! Many comforts and homey touches. Close enough to walk places, far enough for peace and quiet. "
United States
Julie L.
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

Waterfront! Private Dock, Boat Tie-Up & Near Town

Waterfront! Private Dock, Boat Tie-Up & Near Town
Rock Hall
10.0 out of 10, Exceptional, (2)
"A beautiful spot."
United States
Laura S.
Waterfront! Private Dock, Boat Tie-Up & Near Town

Blue Heron Farm Waterfront Chalet

Blue Heron Farm Waterfront Chalet
Chestertown
10.0 out of 10, Exceptional, (1)
"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

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

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Betterton
9.8 out of 10, Exceptional, (46)
"Beautiful, clean, quirky spot. We loved relaxing on the porch overlooking the water. Would definitely recommend and hope to visit again."
United States
Paige J.
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

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

Peaceful getaway convenient to local amenities including beach, boating & food
Rock Hall
9.8 out of 10, Exceptional, (119)
"Great place, calming vibe, located in the middle of everything you may need. "
United States
Kim
Peaceful getaway convenient to local amenities including beach, boating & food
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.
Showing deals for:19 Dec - 21 Dec
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Top Kent County Hotel Reviews

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