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 Church Hill
4.94 out of 5 average rating, 47 reviewsPrivate Peaceful Waterfront House w/ Pool, Hot Tub
20–27 Apr
Home in Rock Hall
4.92 out of 5 average rating, 24 reviewsRockfish Keeper
21–28 Oct
Home in Stevensville
4.98 out of 5 average rating, 62 reviewsBeautiful Kent Island Getaway with Pool
11–18 Dec
Home in Chestertown
4.5 out of 5 average rating, 8 reviewsPrivate pier, pool at waterfront Chestertown home
21–28 Apr
Home in Chestertown
5.0 out of 5 average rating, 8 reviewsChestertown Watson Family Farm
23–30 Dec
Home in Rock Hall
5.0 out of 5 average rating, 6 reviewsThe Mariner's House
23–30 Oct
Home in Rock Hall
4.83 out of 5 average rating, 12 reviewsWaterfront w/pier, Hot Tub, pool, and in town
16–23 Oct
Home in Worton
4.96 out of 5 average rating, 24 reviewsChesapeake Bay Estate; 2 Houses, Beach&Heated Pool
25 Nov – 2 Dec
Weekly house rentals
Home in Chestertown
4.94 out of 5 average rating, 31 reviewsHarbor View Haven | Waterfront w/ HOT TUB + Dock!
13–20 Jul
Home in Rock Hall
5.0 out of 5 average rating, 30 reviewsEastern Neck Water Paradise w/Brick oven & Beach
23 Feb – 2 Mar
Home in Chestertown
5.0 out of 5 average rating, 16 reviewsDown by the River
1–8 Jan
Home in Chestertown
4.96 out of 5 average rating, 24 reviewsRiver Cottage, Chestertown
4–11 Sep
Home in Chestertown
4.89 out of 5 average rating, 27 reviewsBeautifully remodeled home in Historic Chestertown
24 Jun – 1 Jul
Home in Rock Hall
5.0 out of 5 average rating, 66 reviewsCozy 1920's Bungalow Near Water/Local Attractions
20–27 Aug
Home in Chestertown
5.0 out of 5 average rating, 21 reviewsIn Town Chestertown Rancher (1 Block to College)
8–15 Feb
Home in Chestertown
5.0 out of 5 average rating, 24 reviewsMagnolia House ~Historic Downtown w/Private Garden
25 Jan – 1 Feb
Private house rentals
Home in Rock Hall
4.9 out of 5 average rating, 42 reviewsCharming Cape By The Bay!
22–29 Oct
Home in Rock Hall
5.0 out of 5 average rating, 27 reviewsThe Bay House - just a few steps to the bay!
5–12 Mar
Home in Rock Hall
4.95 out of 5 average rating, 20 reviewsEastern Shore Escape in the Heart of Rock Hall
10–17 Mar
Home in Joppatowne
4.93 out of 5 average rating, 15 reviewsMac's Waterfront Wonder
31 Aug – 7 Sep
Home in Rock Hall
4.89 out of 5 average rating, 18 reviewsSpacious Victorian close to everything in RH!
26 Dec – 2 Jan
Home in Stevensville
5.0 out of 5 average rating, 7 reviewsGable’s Landing on the River.
12–19 Dec
Home in Joppatowne
4.9 out of 5 average rating, 31 reviewsWaterfront Oasis for Families/Remote Work
1–8 Nov
Home in Rock Hall
Church Creek Cottage
19–26 Nov
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