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Holiday Rentals in Kent County
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Our top choices for Kent County holiday rentals
Chesapeake Bay Harbor View in a central location to events/restaurants
Chesapeake Bay Harbor View in a central location to events/restaurantsRock 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."
Todd W.
The price is €238
includes taxes & fees
14 Dec - 15 Dec
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 RiverMillington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
Cynthia C.
The price is €110
includes taxes & fees
15 Dec - 16 Dec
First Floor Studio Apartment in Historic Chestertown
First Floor Studio Apartment in Historic ChestertownChestertown
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
Alexander M.
The price is €139
includes taxes & fees
15 Dec - 16 Dec
BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
Roger
The price is €264
includes taxes & fees
1 Jan - 2 Jan 2026
Waterfront Retreat with Private Dock and Beach
Waterfront Retreat with Private Dock and BeachWorton
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!"
Andrea M.
The price is €266
includes taxes & fees
11 Jan - 12 Jan 2026
Grandma’s Cottage will wrap around you like a warm hug
Grandma’s Cottage will wrap around you like a warm hugBetterton
The price is €365
includes taxes & fees
1 Jan - 2 Jan 2026
The price is €174
includes taxes & fees
14 Dec - 15 Dec
Luxe Houseboat with Epic 360 Views of Baltimore Harbor
Luxe Houseboat with Epic 360 Views of Baltimore HarborBaltimore
10.0 out of 10, Exceptional, (11)
"Everything was wonderful - the boat was just as described, even wit a few extra touches that meant a lot - snacks, water bottles, shampoo/conditioner, plenty of hangers, and the SUPER clean, just to name a few!
We would love to stay again! Thank you so much!"
Maggie P.
The price is €490
includes taxes & fees
14 Dec - 15 Dec
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
SpringHill Suites by Marriott Baltimore BWI Airport
10/10 Excellent
Find out more about Kent County
Holiday Homes in Kent County
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