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