Family-friendly holiday rentals in Chestertown
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Chestertown
Guests agree: these family-friendly homes 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 Chestertown family-friendly rentals
Family-friendly home rentals with a hot tub
Flat in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
Townhouse in Baltimore
4.95 out of 5 average rating, 444 reviewsParkfront Hot Tub Haven for Families & Pets
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Home in Edgewater
4.76 out of 5 average rating, 273 reviewsEdgewater/Mayo Getaway!
Home in Harwood
4.94 out of 5 average rating, 119 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
Home in Annapolis
4.84 out of 5 average rating, 94 reviewsRecently Renovated. Chic Cozy Charm. Pubs, Shops
Home in Annapolis
4.86 out of 5 average rating, 156 reviewsCharming Annapolis Water View Home
Townhouse in Annapolis
4.81 out of 5 average rating, 118 reviewsYou'll Never Want to Leave
Family- and pet-friendly home rentals
Guest suite in Arnold
4.85 out of 5 average rating, 514 reviewsSunny Spot Suite, Serene, Annapolis, Naval Academy
Home in Annapolis
4.86 out of 5 average rating, 210 reviewsSpacious Home in Private Neighborhood with Beach
Apartment in Annapolis
4.94 out of 5 average rating, 350 reviewsBrand New Reno in Historic Dist w 2 Parking spots
Home in Annapolis
4.98 out of 5 average rating, 133 reviewsCrab Cakes and Football Historic District
Home in Annapolis
4.97 out of 5 average rating, 116 reviewsGorgeous Historic Downtown Annapolis House
Townhouse in Baltimore
4.87 out of 5 average rating, 268 reviewsParkside Charm & Spaciousness-Family Friendly
Cottage in Deale
4.81 out of 5 average rating, 167 reviewsWatrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Townhouse in Baltimore
4.85 out of 5 average rating, 282 reviewsPark front luxury townhouse
Family-friendly home rentals with a pool
Home in Queenstown
4.81 out of 5 average rating, 142 reviewsBay Breeze Retreat
Home in Arnold
4.9 out of 5 average rating, 86 reviewsAnnapolis Sunset Escape
Flat in Nottingham
4.91 out of 5 average rating, 119 reviewsBright and roomy 2nd floor apt in a private home
Guest house in Stevensville
4.91 out of 5 average rating, 172 reviewsCirca 1700 Chesapeake Colonial Home
Home in Chestertown
5.0 out of 5 average rating, 9 reviewsChestertown Watson Family Farm
Farm stay in Chestertown
4.97 out of 5 average rating, 87 reviewsPiney Grove Farm
Apartment in Annapolis
4.88 out of 5 average rating, 58 reviewsGREAT LOCATION ON SPA CREEK
Home in Queenstown
4.83 out of 5 average rating, 30 reviewsEastern Shore Waterfront Retreat
Quick stats about holiday rentals that are family-friendly in Chestertown
Total rentals
30 properties
Popular amenities
Kitchen, Wifi and Pool
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
1.7K reviews
Nightly prices starting at
£79 before taxes and fees
Destinations to explore
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- Family-friendly rentals United States
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