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
Bungalow in Deale
Cozy waterfront getaway on the Bay
Townhouse in Upper Fells Point
Romantic Hot Tub Getaway, Walk to Fells Point
Cottage in Galena
Tranquil and relaxing escape at Morton Hall
Home in Edgewater
Edgewater/Mayo Getaway!
Home in Annapolis
Recently Renovated. Chic Cozy Charm. Pubs, Shops
Home in Annapolis
Charming Annapolis Water View Home
Townhouse in Annapolis
You'll Never Want to Leave
Home in Arnold
Annapolis Entertainment Complex
Family- and pet-friendly home rentals
Guest suite in Arnold
Sunny Spot Suite, Serene, Annapolis, Naval Academy
Rental unit in Upper Fells Point
Stay in a Former Fells Point Bar! - Private Studio
Home in Annapolis
Spacious Home in Private Neighborhood with Beach
Condo in Annapolis
Brand New Reno in Historic Dist w 2 Parking spots
Home in Annapolis
Crab Cakes and Football Historic District
Townhouse in Patterson Park
Parkside Charm & Spaciousness-Family Friendly
Townhouse in Patterson Park
Park front luxury townhouse
Cottage in Deale
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Family-friendly home rentals with a pool
Home in Saint Michaels
Miles Aweigh
Rental unit in Arnold
Celebrate Summer By Your Private Pool
Home in Queenstown
Bay Breeze Retreat
Home in Harwood
Luxury Home, Sleeps 15, Private Pool, Close to DC
Home in Arnold
Annapolis Sunset Escape
Rental unit in Nottingham
Bright and roomy 2nd floor apt in a private home
Guesthouse in Stevensville
Circa 1700 Chesapeake Colonial Home
Home in Chestertown
Chestertown Watson Family Farm
Quick stats about holiday rentals that are family-friendly in Chestertown
Total rentals
30 properties
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
1.7K reviews
Nightly prices starting at
$161 NZD before taxes and fees
Destinations to explore
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- Family-friendly rentals United States
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- Family-friendly rentals Maryland
- Rentals with a washing machine and dryer Chestertown
- Rentals with a patio Chestertown
- Rentals with outdoor seating Chestertown
- House rentals Chestertown
- Monthly Rentals Chestertown
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