House holiday rentals in Kent County
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Top-rated house rentals in Kent County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Kent County
House rentals with a pool
Home in Rock Hall
4.92 out of 5 average rating, 26 reviewsRockfish Keeper
Home in Stevensville
4.98 out of 5 average rating, 65 reviewsBeautiful Kent Island Getaway with Pool
Home in Chestertown
4.5 out of 5 average rating, 8 reviewsPrivate pier, pool at waterfront Chestertown home
Home in Chestertown
5.0 out of 5 average rating, 9 reviewsChestertown Watson Family Farm
Home in Rock Hall
5.0 out of 5 average rating, 7 reviewsThe Mariner's House
Home in Worton
4.96 out of 5 average rating, 24 reviewsChesapeake Bay Estate; 2 Houses, Beach&Heated Pool
Home in Rock Hall
4.83 out of 5 average rating, 12 reviewsWaterfront w/pier, Hot Tub, pool, and in town
Home in Centreville
5.0 out of 5 average rating, 5 reviewsCreek Cottage at Reed Creek | an ESVR property
Weekly house rentals
Home in Chestertown
5.0 out of 5 average rating, 25 reviewsMagnolia House ~ Historic Downtown, Private Garden
Home in Rock Hall
4.97 out of 5 average rating, 32 reviewsEastern Neck Water Paradise w/Brick oven & Beach
Home in Chestertown
5.0 out of 5 average rating, 54 reviewsLovely Home in Chestertown With Free EV Charging
Home in Chestertown
4.87 out of 5 average rating, 31 reviewsBeautifully remodeled home in Historic Chestertown
Home in Chestertown
5.0 out of 5 average rating, 20 reviewsGoose Haven, new waterfront house on Fairlee Creek
Home in Betterton
5.0 out of 5 average rating, 20 reviewsRuby's Sea Glass Cottage near Betterton Beach
Home in Rock Hall
5.0 out of 5 average rating, 69 reviewsCozy 1920's Bungalow Near Water/Local Attractions
Home in Galena
4.89 out of 5 average rating, 71 reviewsYellow Door Cottage
Private house rentals
Home in Rock Hall
4.91 out of 5 average rating, 23 reviewsThe Blue Jimmy
Home in Stevensville
4.5 out of 5 average rating, 18 reviewsKent Island Luxury Waterfront
Home in Rock Hall
5.0 out of 5 average rating, 27 reviewsThe Bay House - just a few steps to the bay!
Home in Joppatowne
4.94 out of 5 average rating, 17 reviewsMac's Waterfront Wonder
Home in Stevensville
5.0 out of 5 average rating, 7 reviewsGable’s Landing on the River.
Home in Rock Hall
4.89 out of 5 average rating, 18 reviewsSpacious Victorian close to everything in RH!
Home in Joppatowne
4.91 out of 5 average rating, 33 reviewsWaterfront Oasis for Families/Remote Work
Home in Chestertown
4.94 out of 5 average rating, 79 reviewsSimple Living on the Pond
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