Family-friendly vacation rentals in Shady Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Shady Side
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 Shady Side family-friendly rentals
Family-friendly home rentals with a hot tub
Home in Edgewater
4.75 out of 5 average rating, 269 reviewsEdgewater/Mayo Getaway!
Dec 26 – Jan 2
Home in Kent Narrows
5.0 out of 5 average rating, 279 reviewsChester Riverfront At Kent Narrows
Nov 2 – 9
Apartment in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
Dec 14 – 21
Townhouse in Baltimore
4.95 out of 5 average rating, 572 reviewsRomantic Hot Tub Getaway, Walk to Fells Point
Nov 14 – 21
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Dec 12 – 19
Home in Arlington
4.86 out of 5 average rating, 264 reviewsArlington farmhouse w/easy access to everything DC
Aug 19 – 26
Home in Chestertown
5.0 out of 5 average rating, 104 reviewsWaterfront w/Pier &Walking Distance to Chestertown
Mar 6 – 13
Guest suite in Adelphi
4.85 out of 5 average rating, 203 reviewsCozy Suite with Hot Tub and Pool
Jan 13 – 20
Family- and pet-friendly home rentals
Guest suite in Arnold
4.84 out of 5 average rating, 502 reviewsSunny Spot Suite, Serene, Annapolis, Naval Academy
Aug 16 – 23
Home in Cambridge
4.9 out of 5 average rating, 146 reviewsJewell on the Chesapeake
Oct 14 – 21
Apartment in Silver Spring
4.93 out of 5 average rating, 395 reviewsEscape to a Sunny Apartment in a Quiet D.C. Suburb
Oct 2 – 9
Condo in Annapolis
4.94 out of 5 average rating, 347 reviewsBrand New Reno in Historic Dist w 2 Parking spots
Nov 26 – Dec 3
Home in Glen Burnie
4.97 out of 5 average rating, 398 reviewsSecluded acre near BWI and Baltimore
Jun 5 – 12
Home in Annapolis
4.98 out of 5 average rating, 130 reviewsCrab Cakes and Football Historic District
Jul 28 – Aug 4
Apartment in Solomons
4.99 out of 5 average rating, 226 reviewsIsland Breeze Solomons
Nov 2 – 9
Apartment in Washington
4.93 out of 5 average rating, 179 reviewsGracie's Place on Capitol Hill
Jan 22 – 29
Family-friendly home rentals with a pool
Guesthouse in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
Oct 18 – 25
Guest suite in Catonsville
4.94 out of 5 average rating, 470 reviewsRollingside: Two-Room Guest Suite
Aug 19 – 26
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Dec 5 – 12
Home in Lusby
5.0 out of 5 average rating, 111 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Jun 22 – 29
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 22 – 29
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Jun 19 – 26
Cottage in Neavitt
4.88 out of 5 average rating, 17 reviewsGrandview Cottage #2 -A special peaceful place!
Jan 7 – 14
Home in Saint Michaels
4.98 out of 5 average rating, 84 reviewsSM’s Premier Rental Heated Pool opens 4/12
Mar 7 – 14
Quick stats about vacation rentals that are family-friendly in Shady Side
Total rentals
30 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Total number of reviews
800 reviews
Nightly prices starting at
G$18,801 GYD before taxes and fees
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