Family-friendly vacation 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.
Vacation 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
Apartment in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
Home in Edgewater
4.76 out of 5 average rating, 272 reviewsEdgewater/Mayo Getaway!
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Home in Harwood
4.94 out of 5 average rating, 118 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
Home in Annapolis
4.84 out of 5 average rating, 92 reviewsRecently Renovated. Chic Cozy Charm. Pubs, Shops
Home in Annapolis
4.86 out of 5 average rating, 155 reviewsCharming Annapolis Water View Home
Townhouse in Annapolis
4.81 out of 5 average rating, 118 reviewsYou'll Never Want to Leave
Home in Chesapeake City
4.98 out of 5 average rating, 48 reviewsPool Open 4/1 to 10/31! Hot tub open all year!
Family- and pet-friendly home rentals
Guest suite in Arnold
4.85 out of 5 average rating, 512 reviewsSunny Spot Suite, Serene, Annapolis, Naval Academy
Home in Annapolis
4.86 out of 5 average rating, 209 reviewsSpacious Home in Private Neighborhood with Beach
Condo in Annapolis
4.94 out of 5 average rating, 349 reviewsBrand New Reno in Historic Dist w 2 Parking spots
Home in Annapolis
4.98 out of 5 average rating, 132 reviewsCrab Cakes and Football Historic District
Home in Annapolis
4.87 out of 5 average rating, 103 reviewsEntire floor of single-family Annapolis home.
Guesthouse in Stevensville
4.59 out of 5 average rating, 96 reviewsKent Island Waterfront Cottage
Home in Centreville
4.62 out of 5 average rating, 87 reviewsPeaceful Acres Guest House (A Nature's Getaway)
Guesthouse in Annapolis
4.94 out of 5 average rating, 88 reviewsCarriage House near Navy Stadium, parking, pets
Family-friendly home rentals with a pool
Home in Queenstown
4.81 out of 5 average rating, 142 reviewsBay Breeze Retreat
Home in Arnold
4.91 out of 5 average rating, 85 reviewsAnnapolis Sunset Escape
Guesthouse in Stevensville
4.91 out of 5 average rating, 172 reviewsCirca 1700 Chesapeake Colonial Home
Apartment in Nottingham
4.91 out of 5 average rating, 119 reviewsBright and roomy 2nd floor apt in a private 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
Condo 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 vacation 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
$136 CAD before taxes and fees
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