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
Cottage in Galena
4.83 out of 5 average rating, 103 reviewsTranquil and relaxing escape at Morton Hall
Feb 14 – 21
Townhouse in Baltimore
4.95 out of 5 average rating, 438 reviewsParkfront Hot Tub Haven for Families & Pets
Feb 7 – 14
Apartment in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
Jan 16 – 23
Home in Edgewater
4.75 out of 5 average rating, 269 reviewsEdgewater/Mayo Getaway!
Dec 5 – 12
Home in Annapolis
4.83 out of 5 average rating, 89 reviewsRecently Renovated. Chic Cozy Charm. Pubs, Shops
Nov 22 – 29
Home in Annapolis
4.86 out of 5 average rating, 153 reviewsCharming Annapolis Water View Home
Sep 16 – 23
Home in Annapolis
4.83 out of 5 average rating, 116 reviewsYou'll Never Want to Leave
Jan 20 – 27
Home in Chesapeake City
4.98 out of 5 average rating, 48 reviewsPool Open 4/1 to 10/31! Hot tub open all year!
Mar 10 – 17
Family- and pet-friendly home rentals
Condo in Annapolis
4.94 out of 5 average rating, 347 reviewsBrand New Reno in Historic Dist w 2 Parking spots
Aug 15 – 22
Home in Annapolis
4.98 out of 5 average rating, 130 reviewsCrab Cakes and Football Historic District
Jul 27 – Aug 3
Home in Annapolis
4.97 out of 5 average rating, 114 reviewsGorgeous Historic Downtown Annapolis House
Jan 25 – Feb 1
Home in Annapolis
4.85 out of 5 average rating, 206 reviewsSpacious Home in Private Neighborhood with Beach
Oct 25 – Nov 1
Townhouse in Baltimore
4.84 out of 5 average rating, 276 reviewsPark front luxury townhouse
Oct 3 – 10
Home in Annapolis
4.87 out of 5 average rating, 103 reviewsEntire floor of single-family Annapolis home.
May 19 – 26
Home in Centreville
4.62 out of 5 average rating, 87 reviewsPeaceful Acres Guest House (A Nature's Getaway)
Mar 11 – 18
Guesthouse in Stevensville
4.58 out of 5 average rating, 93 reviewsChester River Waterfront Cottage (Love Point Bay)
Sep 15 – 22
Family-friendly home rentals with a pool
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 21 – 28
Home in Arnold
4.91 out of 5 average rating, 85 reviewsAnnapolis Sunset Escape
Oct 28 – Nov 4
Guesthouse in Stevensville
4.91 out of 5 average rating, 172 reviewsCirca 1700 Chesapeake Colonial Home
Oct 6 – 13
Apartment in Nottingham
4.91 out of 5 average rating, 119 reviewsBright and roomy 2nd floor apt in a private home
Sep 25 – Oct 2
Home in Chestertown
5.0 out of 5 average rating, 8 reviewsChestertown Watson Family Farm
Dec 23 – 30
Farm stay in Chestertown
4.97 out of 5 average rating, 86 reviewsPiney Grove Farm
Nov 19 – 26
Condo in Annapolis
4.88 out of 5 average rating, 58 reviewsGREAT LOCATION ON SPA CREEK
Jan 24 – 31
Home in Queenstown
4.83 out of 5 average rating, 30 reviewsEastern Shore Waterfront Retreat
Jan 3 – 10
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
G$20,902 GYD before taxes and fees
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- House rentals Chestertown
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