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
4.76 out of 5 average rating, 270 reviewsEdgewater/Mayo Getaway!
Aug 23 – 30
Home in Kent Narrows
5.0 out of 5 average rating, 280 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
Apr 28 – May 5
Townhouse in Baltimore
4.95 out of 5 average rating, 572 reviewsRomantic Hot Tub Getaway, Walk to Fells Point
Mar 16 – 23
Home in Arlington
4.86 out of 5 average rating, 266 reviewsArlington farmhouse w/easy access to everything DC
Oct 29 – Nov 5
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Oct 17 – 24
Home in Chestertown
5.0 out of 5 average rating, 104 reviewsWaterfront w/Pier &Walking Distance to Chestertown
Oct 22 – 29
Guest suite in Adelphi
4.85 out of 5 average rating, 203 reviewsCozy Suite with Hot Tub and Pool
Jan 15 – 22
Family- and pet-friendly home rentals
Home in Cambridge
4.89 out of 5 average rating, 111 reviewsDorothy's Chesapeake Delight
Oct 19 – 26
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
Guest suite in Chestertown
4.99 out of 5 average rating, 193 reviewsBeautiful Waterfront Chestertown Getaway
Jul 9 – 16
Condo in Annapolis
4.94 out of 5 average rating, 347 reviewsBrand New Reno in Historic Dist w 2 Parking spots
Mar 1 – 8
Home in Glen Burnie
4.97 out of 5 average rating, 399 reviewsSecluded acre near BWI and Baltimore
Oct 15 – 22
Home in Annapolis
4.98 out of 5 average rating, 130 reviewsCrab Cakes and Football Historic District
Jan 23 – 30
Home in Annapolis
4.85 out of 5 average rating, 206 reviewsSpacious Home in Private Neighborhood with Beach
Oct 25 – Nov 1
Home in Annapolis
4.97 out of 5 average rating, 114 reviewsGorgeous Historic Downtown Annapolis House
Feb 1 – 8
Family-friendly home rentals with a pool
Guesthouse in Highland
4.98 out of 5 average rating, 264 reviewsWoodland Retreat
Sep 6 – 13
Guest suite in Catonsville
4.94 out of 5 average rating, 470 reviewsRollingside: Two-Room Guest Suite
Oct 5 – 12
Home in Lusby
5.0 out of 5 average rating, 112 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Oct 13 – 20
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Jan 28 – Feb 4
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 24 – Dec 1
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Jun 22 – 29
Cottage in Neavitt
4.88 out of 5 average rating, 17 reviewsGrandview Cottage #2 -A special peaceful place!
Dec 18 – 25
Home in Saint Michaels
4.98 out of 5 average rating, 84 reviewsSM’s Premier Rental Heated Pool opens 4/12
Mar 8 – 15
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
€ 84 before taxes and fees
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