Family-friendly holiday houses 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.
Holiday 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
4.76 out of 5 average rating, 273 reviewsEdgewater/Mayo Getaway!
Home in Kent Narrows
5.0 out of 5 average rating, 281 reviewsChester Riverfront At Kent Narrows
Apartment in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
Townhouse in Baltimore
4.95 out of 5 average rating, 582 reviewsRomantic Hot Tub Getaway, Walk to Fells Point
Home in Arlington
4.86 out of 5 average rating, 271 reviewsArlington farmhouse w/easy access to everything DC
Home in Severn
4.81 out of 5 average rating, 107 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Guest suite in Adelphi
4.85 out of 5 average rating, 203 reviewsCozy Suite with Hot Tub and Pool
Home in Chestertown
5.0 out of 5 average rating, 105 reviewsWaterfront w/Pier &Walking Distance to Chestertown
Family- and pet-friendly home rentals
Guest suite in Arnold
4.85 out of 5 average rating, 514 reviewsSunny Spot Suite, Serene, Annapolis, Naval Academy
Home in Annapolis
4.86 out of 5 average rating, 210 reviewsSpacious Home in Private Neighborhood with Beach
Home in Cambridge
4.91 out of 5 average rating, 148 reviewsJewell on the Chesapeake
Apartment in Silver Spring
4.93 out of 5 average rating, 398 reviewsEscape to a Sunny Apartment in a Quiet D.C. Suburb
Home in Glen Burnie
4.97 out of 5 average rating, 402 reviewsSecluded acre near BWI and Baltimore
Apartment in Solomons
4.99 out of 5 average rating, 237 reviewsIsland Breeze Solomons
Apartment in Washington
4.99 out of 5 average rating, 159 reviewsCapitol Hill comfy 1BR basement apt - Free parking
Condo in Annapolis
4.94 out of 5 average rating, 351 reviewsBrand New Reno in Historic Dist w 2 Parking spots
Family-friendly home rentals with a pool
Guesthouse in Highland
4.98 out of 5 average rating, 267 reviewsWoodland Retreat
Home in Saint Michaels
4.97 out of 5 average rating, 240 reviewsMiles Aweigh
Guest suite in Catonsville
4.94 out of 5 average rating, 474 reviewsRollingside: Two-Room Guest Suite
Home in Queenstown
4.81 out of 5 average rating, 142 reviewsBay Breeze Retreat
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Cottage in Neavitt
4.89 out of 5 average rating, 18 reviewsGrandview Cottage #2 -A special peaceful place!
Home in Saint Michaels
4.98 out of 5 average rating, 84 reviewsSM’s Premier Rental Heated Pool opens 4/12
Home in Arnold
4.9 out of 5 average rating, 86 reviewsAnnapolis Sunset Escape
Quick stats about accommodation & holiday rentals that are family-friendly in Shady Side
Total rentals
30 properties
Wi-Fi availability
20 properties include access to Wi-Fi
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
$137 AUD before taxes and fees
Destinations to explore
- Baltimore Accommodation & holiday rentals
- Ocean City Accommodation & holiday rentals
- Cape May Holiday rentals
- Wildwood Holiday rentals
- Rehoboth Beach Accommodation & holiday rentals
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- Deep Creek Lake Holiday rentals
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- Jersey City Holiday rentals
- The Hamptons Holiday rentals
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