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
Bungalow in Deale
4.87 out of 5 average rating, 356 reviewsCozy waterfront getaway on the Bay
Feb 13 – 20
Townhouse in Baltimore
4.95 out of 5 average rating, 570 reviewsRomantic Hot Tub Getaway, Walk to Fells Point
Mar 27 – Apr 3
Cabin in North East
4.96 out of 5 average rating, 154 reviewsWaterfront Cabin on the Chesapeake
Feb 15 – 22
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Jan 28 – Feb 4
Apartment in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
Oct 30 – Nov 6
Home in Harwood
4.94 out of 5 average rating, 117 reviewsLuxury Home, Sleeps 15, Private Pool, Close to DC
May 8 – 15
Home in Deale
4.98 out of 5 average rating, 113 reviewsChesapeake Waterfront-Hot Tub-Kayaks-King Bed
Jul 18 – 25
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Nov 9 – 16
Family- and pet-friendly home rentals
Guesthouse in Glen Burnie
4.81 out of 5 average rating, 155 reviewsPrivate 1 bedroom house
Oct 27 – Nov 3
Home in Glen Burnie
4.97 out of 5 average rating, 397 reviewsSecluded acre near BWI and Baltimore
Jul 25 – Aug 1
Home in Perryville
4.93 out of 5 average rating, 181 reviewsTop of the Chesapeake - Private Waterfront Home
Feb 2 – 9
Apartment in Baltimore
4.86 out of 5 average rating, 786 reviewsStay in a Former Fells Point Bar! - Private Studio
Feb 10 – 17
Condo in Annapolis
4.94 out of 5 average rating, 347 reviewsBrand New Reno in Historic Dist w 2 Parking spots
Feb 22 – Mar 1
Home in Baltimore
4.99 out of 5 average rating, 147 reviewsCharming Victorian home in Roland Park, Baltimore.
Apr 18 – 25
Home in Annapolis
4.98 out of 5 average rating, 130 reviewsCrab Cakes and Football Historic District
Aug 27 – Sep 3
Guest suite in Baltimore
4.98 out of 5 average rating, 104 reviewsGorgeous Mid-Century Gem near Lake Roland
Nov 7 – 14
Family-friendly home rentals with a pool
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Dec 3 – 10
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 19 – 26
Home in Saint Michaels
4.98 out of 5 average rating, 84 reviewsSM’s Premier Rental Heated Pool opens 4/12
Jan 30 – Feb 6
Villa in Easton
4.95 out of 5 average rating, 38 reviewsSt. Michaels Waterfront-Pool/Kayak/Pier/Firepit
May 7 – 14
Cabin in Saint Michaels
4.99 out of 5 average rating, 97 reviewsTrue St. Michaels 6 Acre Waterfront w/heated pool
Apr 18 – 25
Home in Arnold
4.91 out of 5 average rating, 85 reviewsAnnapolis Sunset Escape
Oct 27 – Nov 3
Guesthouse in Stevensville
4.91 out of 5 average rating, 172 reviewsCirca 1700 Chesapeake Colonial Home
Oct 5 – 12
Apartment in Nottingham
4.91 out of 5 average rating, 119 reviewsBright and roomy 2nd floor apt in a private home
Sep 27 – Oct 4
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
€ 93 before taxes and fees
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