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 13 – 20
Home in Church Hill
4.94 out of 5 average rating, 47 reviewsPrivate Peaceful Waterfront House w/ Pool, Hot Tub
Aug 29 – Sep 5
Home in Stevensville
4.98 out of 5 average rating, 62 reviewsBeautiful Kent Island Getaway with Pool
Apr 1 – 8
Home in Chestertown
4.5 out of 5 average rating, 8 reviewsPrivate pier, pool at waterfront Chestertown home
Apr 21 – 28
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 26 – Nov 2
Home in Worton
4.96 out of 5 average rating, 24 reviewsChesapeake Bay Estate; 2 Houses, Beach&Heated Pool
Jan 10 – 17
Weekly house rentals
Home in Chestertown
5.0 out of 5 average rating, 25 reviews125 High - Luxury Historical Brick Victorian
Apr 5 – 12
Home in Chestertown
4.94 out of 5 average rating, 31 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 24 – Mar 3
Home in Chestertown
5.0 out of 5 average rating, 16 reviewsDown by the River
Jan 2 – 9
Home in Chestertown
4.96 out of 5 average rating, 24 reviewsRiver Cottage, Chestertown
May 18 – 25
Home in Rock Hall
4.95 out of 5 average rating, 22 reviewsThe Blue Jimmy
Feb 5 – 12
Home in Betterton
5.0 out of 5 average rating, 18 reviewsRuby's Sea Glass Cottage near Betterton Beach
Oct 15 – 22
Home in Chestertown
5.0 out of 5 average rating, 24 reviewsMagnolia House ~Historic Downtown w/Private Garden
Aug 4 – 11
Private house rentals
Home in Rock Hall
4.9 out of 5 average rating, 42 reviewsCharming Cape By The Bay!
Jan 2 – 9
Home in Rock Hall
5.0 out of 5 average rating, 27 reviewsThe Bay House - just a few steps to the bay!
Mar 6 – 13
Home in Rock Hall
4.95 out of 5 average rating, 20 reviewsEastern Shore Escape in the Heart of Rock Hall
Mar 11 – 18
Home in Joppatowne
4.93 out of 5 average rating, 15 reviewsMac's Waterfront Wonder
Oct 27 – Nov 3
Home in Rock Hall
4.89 out of 5 average rating, 18 reviewsSpacious Victorian close to everything in RH!
Dec 27 – Jan 3
Home in Stevensville
5.0 out of 5 average rating, 7 reviewsGable’s Landing on the River.
Apr 21 – 28
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 20 – 27
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