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
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Popular amenities for Kent County house rentals
House rentals with a pool
Home in Millington
4.91 out of 5 average rating, 34 reviewsThe Peaceful Getaway (with private pool & hot tub)
Jan. 3 – 10
Home in Church Hill
4.94 out of 5 average rating, 47 reviewsPrivate Peaceful Waterfront House w/ Pool, Hot Tub
Apr. 18 – 25
Home in Rock Hall
4.92 out of 5 average rating, 24 reviewsRockfish Keeper
Sep. 23 – 30
Home in Stevensville
4.98 out of 5 average rating, 61 reviewsBeautiful Kent Island Getaway with Pool
Jan. 4 – 11
Home in Chestertown
4.5 out of 5 average rating, 8 reviewsPrivate pier, pool at waterfront Chestertown home
Feb. 9 – 16
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. 23 – 30
Weekly house rentals
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. 21 – 28
Home in Chestertown
4.96 out of 5 average rating, 24 reviewsRiver Cottage, Chestertown
Jul. 7 – 14
Home in Chestertown
5.0 out of 5 average rating, 16 reviewsDown by the River
Dec. 30 – Jan. 6
Home in Chestertown
5.0 out of 5 average rating, 21 reviewsIn Town Chestertown Rancher (1 Block to College)
Feb. 5 – 12
Home in Rock Hall
4.95 out of 5 average rating, 22 reviewsThe Blue Jimmy
Nov. 19 – 26
Home in Chestertown
5.0 out of 5 average rating, 24 reviewsMagnolia House ~Historic Downtown w/Private Garden
Feb. 5 – 12
Home in Betterton
5.0 out of 5 average rating, 18 reviewsRuby's Sea Glass Cottage near Betterton Beach
Sep. 11 – 18
Private house rentals
Home in Joppatowne
4.93 out of 5 average rating, 15 reviewsMac's Waterfront Wonder
Oct. 27 – Nov. 3
Home in Rock Hall
4.95 out of 5 average rating, 20 reviewsEastern Shore Escape in the Heart of Rock Hall
Oct. 19 – 26
Home in Stevensville
5.0 out of 5 average rating, 7 reviewsGable’s Landing on the River.
Jan. 11 – 18
Home in Rock Hall
4.89 out of 5 average rating, 18 reviewsSpacious Victorian close to everything in RH!
Dec. 24 – 31
Home in Joppatowne
4.9 out of 5 average rating, 31 reviewsWaterfront Oasis for Families/Remote Work
Jan. 15 – 22
Home in Rock Hall
Church Creek Cottage
Nov. 17 – 24
Home in Chestertown
4.93 out of 5 average rating, 76 reviewsSimple Living on the Pond
Jul. 18 – 25
Home in Chestertown
5.0 out of 5 average rating, 8 reviewsHeron Creek
Mar. 9 – 16
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