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
Townhouse in Upper Fells Point
4.95 out of 5 average rating, 600 reviewsRomantic Hot Tub Getaway, Walk to Fells Point
Rental unit in North East
4.98 out of 5 average rating, 225 reviewsDusty's House
Home in Deale
4.98 out of 5 average rating, 124 reviewsChesapeake Waterfront Kayaks-Fish & Crabbing
Home in Edgewater
4.76 out of 5 average rating, 275 reviewsEdgewater/Mayo Getaway!
Townhouse in Annapolis
4.82 out of 5 average rating, 120 reviewsYou'll Never Want to Leave
Home in Annapolis
4.84 out of 5 average rating, 96 reviewsRecently Renovated. Chic Cozy Charm. Pubs, Shops
Home in Chestertown
5 out of 5 average rating, 107 reviewsWaterfront w/Pier &Walking Distance to Chestertown
Bungalow in Deale
4.85 out of 5 average rating, 368 reviewsCozy waterfront getaway on the Bay
Family- and pet-friendly home rentals
Guesthouse in Glen Burnie
4.81 out of 5 average rating, 160 reviewsPrivate 1 bedroom house
Rental unit in Upper Fells Point
4.86 out of 5 average rating, 792 reviewsStay in a Former Fells Point Bar! - Private Studio
Rental unit in Edgewater
4.9 out of 5 average rating, 416 reviewsPet Friendly Garden Apartment Near Annapolis
Home in Glen Burnie
4.97 out of 5 average rating, 413 reviewsSecluded acre near BWI and Baltimore
Home in Perryville
4.92 out of 5 average rating, 188 reviewsTop of the Chesapeake - Private Waterfront Home
Townhouse in Roland Park
4.74 out of 5 average rating, 117 reviewsWhole Townhouse+ all amenities
Condo in Annapolis
4.94 out of 5 average rating, 359 reviewsBrand New Reno in Historic Dist w 2 Parking spots
Townhouse in Federal Hill - Montgomery
4.89 out of 5 average rating, 261 reviewsBmore@Home Fed Hill Rowhome-Conv Ctr,Harbor
Family-friendly home rentals with a pool
Home in Saint Michaels
4.97 out of 5 average rating, 244 reviewsMiles Aweigh
Home in Severn
4.83 out of 5 average rating, 116 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Home in Queenstown
4.82 out of 5 average rating, 148 reviewsBay Breeze Retreat
Rental unit in Arnold
4.96 out of 5 average rating, 164 reviewsCelebrate Summer By Your Private Pool
Home in Harwood
4.94 out of 5 average rating, 122 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
Home in Saint Michaels
4.98 out of 5 average rating, 89 reviewsSM’s Premier Rental Heated Pool opens 4/12
Villa in Easton
4.95 out of 5 average rating, 40 reviewsSt. Michaels Waterfront-Pool/Kayak/Pier/Firepit
Home in Arnold
4.88 out of 5 average rating, 25 reviewsAnnapolis Entertainment Complex
Quick stats about vacation rentals that are family-friendly in Chestertown
Total rentals
30 properties
Nightly prices starting at
$100 before taxes and fees
Total number of reviews
1.8K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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