Family-friendly holiday 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.
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, 272 reviewsEdgewater/Mayo Getaway!
Home in Kent Narrows
5.0 out of 5 average rating, 280 reviewsChester Riverfront At Kent Narrows
Flat in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
Home in Severn
4.82 out of 5 average rating, 105 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Townhouse in Baltimore
4.95 out of 5 average rating, 580 reviewsRomantic Hot Tub Getaway, Walk to Fells Point
Guest suite in Adelphi
4.85 out of 5 average rating, 203 reviewsCozy Suite with Hot Tub and Pool
Home in Arlington
4.86 out of 5 average rating, 267 reviewsArlington farmhouse w/easy access to everything DC
Home in Chestertown
5.0 out of 5 average rating, 105 reviewsWaterfront w/Pier &Walking Distance to Chestertown
Family- and pet-friendly home rentals
Flat in Silver Spring
4.93 out of 5 average rating, 395 reviewsEscape to a Sunny Apartment in a Quiet D.C. Suburb
Guest suite in Arnold
4.85 out of 5 average rating, 506 reviewsSunny Spot Suite, Serene, Annapolis, Naval Academy
Home in Cambridge
4.89 out of 5 average rating, 111 reviewsDorothy's Chesapeake Delight
Apartment in Annapolis
4.94 out of 5 average rating, 349 reviewsBrand New Reno in Historic Dist w 2 Parking spots
Home in Glen Burnie
4.97 out of 5 average rating, 402 reviewsSecluded acre near BWI and Baltimore
Home in Annapolis
4.86 out of 5 average rating, 208 reviewsSpacious Home in Private Neighborhood with Beach
Flat in Solomons
4.99 out of 5 average rating, 231 reviewsIsland Breeze Solomons
Flat in Washington
4.94 out of 5 average rating, 556 reviewsCapitol, Union Station, Romantic, Walkable Apt
Family-friendly home rentals with a pool
Home in Saint Michaels
4.97 out of 5 average rating, 239 reviewsMiles Aweigh
Guest suite in Catonsville
4.94 out of 5 average rating, 470 reviewsRollingside: Two-Room Guest Suite
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Apartment in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Cottage in Neavitt
4.88 out of 5 average rating, 17 reviewsGrandview Cottage #2 -A special peaceful place!
Cabin in Saint Michaels
4.99 out of 5 average rating, 100 reviewsTrue St. Michaels 6 Acre Waterfront w/heated pool
Home in Saint Michaels
4.98 out of 5 average rating, 84 reviewsSM’s Premier Rental Heated Pool opens 4/12
Home in Arnold
4.91 out of 5 average rating, 85 reviewsAnnapolis Sunset Escape
Quick stats about holiday 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
€ 83 before taxes and fees
Destinations to explore
- Baltimore Holiday rentals
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