House vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Kent County house rentals
House rentals with a pool
Home in Rock Hall
4.92 out of 5 average rating, 24 reviewsRockfish Keeper
Oct 17 – 24
Home in Church Hill
4.94 out of 5 average rating, 47 reviewsPrivate Peaceful Waterfront House w/ Pool, Hot Tub
Aug 30 – Sep 6
Home in Stevensville
4.98 out of 5 average rating, 62 reviewsBeautiful Kent Island Getaway with Pool
Dec 24 – 31
Home in Chestertown
4.5 out of 5 average rating, 8 reviewsPrivate pier, pool at waterfront Chestertown home
Sep 14 – 21
Home in Chestertown
5.0 out of 5 average rating, 8 reviewsChestertown Watson Family Farm
Dec 23 – 30
Home in Rock Hall
5.0 out of 5 average rating, 6 reviewsThe Mariner's House
Oct 23 – 30
Home in Rock Hall
4.83 out of 5 average rating, 12 reviewsWaterfront w/pier, Hot Tub, pool, and in town
Oct 27 – Nov 3
Home in Worton
4.96 out of 5 average rating, 24 reviewsChesapeake Bay Estate; 2 Houses, Beach&Heated Pool
Mar 25 – Apr 1
Weekly house rentals
Home in Rock Hall
5.0 out of 5 average rating, 66 reviewsCozy 1920's Bungalow Near Water/Local Attractions
Aug 31 – Sep 7
Home in Chestertown
4.94 out of 5 average rating, 32 reviewsHarbor View Haven | Waterfront w/ HOT TUB + Dock!
Jul 13 – 20
Home in Rock Hall
5.0 out of 5 average rating, 30 reviewsEastern Neck Water Paradise w/Brick oven & Beach
Feb 25 – Mar 4
Home in Chestertown
5.0 out of 5 average rating, 16 reviewsDown by the River
Jul 17 – 24
Home in Chestertown
4.96 out of 5 average rating, 24 reviewsRiver Cottage, Chestertown
Jun 9 – 16
Home in Chestertown
4.86 out of 5 average rating, 28 reviewsBeautifully remodeled home in Historic Chestertown
Jul 14 – 21
Home in Chestertown
5.0 out of 5 average rating, 21 reviewsIn Town Chestertown Rancher (1 Block to College)
Aug 9 – 16
Home in Rock Hall
4.95 out of 5 average rating, 22 reviewsThe Blue Jimmy
Jul 24 – 31
Private house rentals
Home in Rock Hall
4.9 out of 5 average rating, 42 reviewsCharming Cape By The Bay!
Mar 27 – Apr 3
Home in Rock Hall
5.0 out of 5 average rating, 27 reviewsThe Bay House - just a few steps to the bay!
Mar 7 – 14
Home in Rock Hall
4.95 out of 5 average rating, 20 reviewsEastern Shore Escape in the Heart of Rock Hall
Mar 12 – 19
Home in Joppatowne
4.93 out of 5 average rating, 15 reviewsMac's Waterfront Wonder
Oct 27 – Nov 3
Home in Stevensville
5.0 out of 5 average rating, 7 reviewsGable’s Landing on the River.
Oct 27 – Nov 3
Home in Rock Hall
4.89 out of 5 average rating, 18 reviewsSpacious Victorian close to everything in RH!
Dec 28 – Jan 4
Home in Joppatowne
4.9 out of 5 average rating, 31 reviewsWaterfront Oasis for Families/Remote Work
Sep 25 – Oct 2
Home in Rock Hall
Church Creek Cottage
Nov 21 – 28
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