Kid-friendly holiday rentals in Kent County
Find and book unique family-friendly rentals on Airbnb
Top-rated family-friendly rentals in Kent County
Guests agree: these family-friendly rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kent County family-friendly rentals
Kid-friendly house rentals
Home in Chestertown
4.89 out of 5 average rating, 27 reviewsBeautifully remodeled home in Historic Chestertown
14–21 Jul
Home in Chestertown
4.98 out of 5 average rating, 44 reviews2 Beds, 2.5 Baths, Perfect Downtown Location
5–12 Jun
Home in Chestertown
5.0 out of 5 average rating, 51 reviewsLovely, Recently-Renovated Home in Chestertown
22–29 Dec
Home in Chestertown
4.96 out of 5 average rating, 73 reviewsCozy 3-bedroom home w/ screened in porch & firepit
4–11 Dec
Home in Millington
4.91 out of 5 average rating, 34 reviewsThe Peaceful Getaway (with private pool & hot tub)
10–17 Oct
Home in Chestertown
5.0 out of 5 average rating, 76 reviewsRiver front cottage with private dock & water fun
10–17 Dec
Home in Chestertown
5.0 out of 5 average rating, 38 reviewsWaterfront house with private dock & kayaks!
25 Nov – 2 Dec
Home in Rock Hall
5.0 out of 5 average rating, 18 reviewsChesapeake Bay Retreat w/ Views!
20–27 Dec
Family-friendly apartment rentals
Flat in Chestertown
4.92 out of 5 average rating, 97 reviewsDowntown Studio Apartment
22–29 Mar
Flat in Rock Hall
5.0 out of 5 average rating, 78 reviewsInspiration Guest Suite - Cinnamon By The Bay
25 Nov – 2 Dec
Flat in Worton
5.0 out of 5 average rating, 16 reviewsElliott House Historic Home Near Chesapeake Bay
24 Jun – 1 Jul
Flat in Chestertown
4.92 out of 5 average rating, 62 reviews1-br apt in downtown Chestertown
24 Jun – 1 Jul
Flat in Chestertown
5.0 out of 5 average rating, 46 reviewsBright, new apartment in the heart of Chestertown
31 Dec – 7 Jan
Flat in Chestertown
4.98 out of 5 average rating, 88 reviewsRIVER WATCH
15–22 Sept
Flat in Stevensville
New place to stayRelax Inn
15–22 Sept
Flat in Rock Hall
5.0 out of 5 average rating, 8 reviewsKnot's Landing, spacious Apt. downtown Rock Hall
25 Aug – 1 Sept
Destinations to explore
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