Pet-friendly holiday rentals in Kent County
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Top-rated pet-friendly home rentals in Kent County
Guests agree: these pet-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for Kent County pet-friendly home rentals
Pet-friendly house rentals
Home in Kennedyville
4.89 out of 5 average rating, 72 reviewsPerfect for Hunters on the Eastern Shore
14–21 Jul
Home in Rock Hall
4.9 out of 5 average rating, 29 reviewsBayside cottage steps from the harbor
14–21 Oct
Home in Rock Hall
5.0 out of 5 average rating, 9 reviewsWaterfront w/upper sundeck and kayaks/paddleboad
20–27 Dec
Home in Stevensville
5.0 out of 5 average rating, 51 reviewsLove Point Idyll - 240' Private Beachfront
18–25 Feb
Home in Middle River
5.0 out of 5 average rating, 12 reviewsWaterfront Home with Private Beach, Stunning Views
11–18 Jan
Home in Centreville
4.62 out of 5 average rating, 87 reviewsPeaceful Acres Guest House (A Nature's Getaway)
1–8 Jul
Home in Rock Hall
4.84 out of 5 average rating, 113 reviewsPirates Perch
8–15 Mar
Home in Galena
4.67 out of 5 average rating, 3 reviewsOff the Hook Nautical Nook
30 May – 6 Jun
Pet-friendly home rentals with a pool
Bungalow in Rock Hall
4.94 out of 5 average rating, 32 reviewsWelcome to Mermaid Haven!
16–23 Oct
Home in Stevensville
4.98 out of 5 average rating, 62 reviewsBeautiful Kent Island Getaway with Pool
19–26 Mar
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
Farm stay in Chestertown
4.97 out of 5 average rating, 86 reviewsPiney Grove Farm
18–25 Nov
Home in Rock Hall
4.83 out of 5 average rating, 12 reviewsWaterfront w/pier, Hot Tub, pool, and in town
24–31 Oct
Home in Worton
4.96 out of 5 average rating, 24 reviewsChesapeake Bay Estate; 2 Houses, Beach&Heated Pool
13–20 Jan
Private, pet-friendly home rentals
Townhouse in Rock Hall
4.91 out of 5 average rating, 45 reviewsWalking Distance to Marinas & Main St!
8–15 May
Guest house in Stevensville
4.58 out of 5 average rating, 93 reviewsChester River Waterfront Cottage (Love Point Bay)
14–21 Sept
Guest suite in Stevensville
4.89 out of 5 average rating, 9 reviewsLakeside Retreat on Kent Island: Sleeps up to 10
7–14 May
Campsite in Millington
4.94 out of 5 average rating, 32 reviewsCanoein’ Sue’s Campsite on the Chester River
17–24 Sept
Farm stay in Chestertown
4.94 out of 5 average rating, 108 reviewsOutrange at Blue Heron Farm
2–9 Mar
Cottage in Rock Hall
4.9 out of 5 average rating, 109 reviewsCottage with Modern Updates - Walk to Waterfront!
21–28 Oct
Guest suite in Centreville
5.0 out of 5 average rating, 7 reviewsHGTV Quality private guest suite, country getaway
11–18 Jun
Farm stay in Centreville
5.0 out of 5 average rating, 23 reviewsFarm Stay at Lansdowne Manor
20–27 Jan
Destinations to explore
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