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!
Nov 25 – Dec 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
Feb 27 – Mar 6
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
Feb 5 – 12
Townhouse in Baltimore
4.95 out of 5 average rating, 572 reviewsRomantic Hot Tub Getaway, Walk to Fells Point
Apr 21 – 28
Home in Arlington
4.86 out of 5 average rating, 265 reviewsArlington farmhouse w/easy access to everything DC
Sep 6 – 13
Home in Chestertown
5.0 out of 5 average rating, 104 reviewsWaterfront w/Pier &Walking Distance to Chestertown
Dec 12 – 19
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
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
Sep 12 – 19
Guest suite in Chestertown
4.99 out of 5 average rating, 192 reviewsBeautiful Waterfront Chestertown Getaway
Oct 2 – 9
Condo in Annapolis
4.94 out of 5 average rating, 347 reviewsBrand New Reno in Historic Dist w 2 Parking spots
Jan 1 – 8
Home in Glen Burnie
4.97 out of 5 average rating, 399 reviewsSecluded acre near BWI and Baltimore
Jun 19 – 26
Home in Annapolis
4.98 out of 5 average rating, 130 reviewsCrab Cakes and Football Historic District
Jul 29 – Aug 5
Apartment in Washington
4.93 out of 5 average rating, 553 reviewsCapitol, Union Station, Romantic, Walkable Apt
Jul 23 – 30
Home in Annapolis
4.85 out of 5 average rating, 206 reviewsSpacious Home in Private Neighborhood with Beach
Oct 25 – Nov 1
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
Sep 2 – 9
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
Dec 7 – 14
Home in Lusby
5.0 out of 5 average rating, 112 reviewsHistoric Rousby Hall, Waterfront, Patuxent River
Jun 27 – Jul 4
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
Nov 23 – 30
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
Jun 20 – 27
Cottage in Neavitt
4.88 out of 5 average rating, 17 reviewsGrandview Cottage #2 -A special peaceful place!
Dec 16 – 23
Home in Saint Michaels
4.98 out of 5 average rating, 84 reviewsSM’s Premier Rental Heated Pool opens 4/12
Feb 27 – Mar 6
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
$90 before taxes and fees
Destinations to explore
- Baltimore Vacation rentals
- Ocean City Vacation rentals
- Cape May Vacation rentals
- Wildwood Vacation rentals
- Rehoboth Beach Vacation rentals
- Arlington Vacation rentals
- Washington Vacation rentals
- Deep Creek Lake Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Family-friendly rentals United States
- Family-friendly rentals Washington
- Family-friendly rentals Baltimore
- Family-friendly rentals Maryland
- Family-friendly rentals Maryland
- House rentals Shady Side
- Rentals with outdoor seating Shady Side
- Rentals with a patio Shady Side
- Rentals with a washer and dryer Shady Side
- Monthly Rentals Shady Side
- Family-friendly rentals Anne Arundel County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes