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
4.75 out of 5 average rating, 269 reviewsEdgewater/Mayo Getaway!
3–10 Oct
Home in Kent Narrows
5.0 out of 5 average rating, 278 reviewsChester Riverfront At Kent Narrows
19–26 Oct
Apartment in Arnold
4.96 out of 5 average rating, 158 reviewsCelebrate Summer By Your Private Pool
13–20 Sep
Home in Severn
4.81 out of 5 average rating, 102 reviewsLarge Home with Pool & 7 bedrooms; sleeps 21
28 Mar – 4 Apr
Home in Arlington
4.86 out of 5 average rating, 264 reviewsArlington farmhouse w/easy access to everything DC
29 Oct – 5 Nov
Home in Chestertown
5.0 out of 5 average rating, 104 reviewsWaterfront w/Pier &Walking Distance to Chestertown
9–16 Nov
Guest suite in Adelphi
4.85 out of 5 average rating, 203 reviewsCozy Suite with Hot Tub and Pool
7–14 Jul
Home in Annapolis
4.83 out of 5 average rating, 89 reviewsRecently Renovated. Chic Cozy Charm. Pubs, Shops
26 Dec – 2 Jan
Family- and pet-friendly home rentals
Apartment in Silver Spring
4.93 out of 5 average rating, 395 reviewsEscape to a Sunny Apartment in a Quiet D.C. Suburb
15–22 Oct
Home in Cambridge
4.9 out of 5 average rating, 146 reviewsJewell on the Chesapeake
2–9 Aug
Home in Glen Burnie
4.97 out of 5 average rating, 396 reviewsSecluded acre near BWI and Baltimore
27 Sep – 4 Oct
Condo in Annapolis
4.94 out of 5 average rating, 347 reviewsBrand New Reno in Historic Dist w 2 Parking spots
20–27 Feb
Apartment in Washington
4.94 out of 5 average rating, 550 reviewsCapitol, Union Station, Romantic, Walkable Apt
7–14 Jul
Home in Annapolis
4.98 out of 5 average rating, 131 reviewsCrab Cakes and Football Historic District
29 Dec – 5 Jan
Guesthouse in Glen Burnie
4.81 out of 5 average rating, 155 reviewsPrivate 1 bedroom house
24–31 Dec
Apartment in Washington
4.86 out of 5 average rating, 525 reviewsRelaxing, Modern, Central Location on Capitol Hill
13–20 Jul
Family-friendly home rentals with a pool
Home in Queenstown
4.81 out of 5 average rating, 143 reviewsBay Breeze Retreat
15–22 Nov
Home in Saint Michaels
4.97 out of 5 average rating, 238 reviewsMiles Aweigh
4–11 Apr
Condo in Oxon Hill
4.88 out of 5 average rating, 132 reviewsModern Apartments available at National Harbor
13–20 Jun
Cottage in Neavitt
4.88 out of 5 average rating, 17 reviewsGrandview Cottage #2 -A special peaceful place!
1–8 Jan
Cabin in Saint Michaels
4.99 out of 5 average rating, 97 reviewsTrue St. Michaels 6 Acre Waterfront w/heated pool
16–23 Jan
Home in Saint Michaels
4.98 out of 5 average rating, 84 reviewsSM’s Premier Rental Heated Pool opens 4/12
16–23 Apr
Home in Arnold
4.91 out of 5 average rating, 85 reviewsAnnapolis Sunset Escape
14–21 Jan
Villa in Easton
4.95 out of 5 average rating, 38 reviewsSt. Michaels Waterfront-Pool/Kayak/Pier/Firepit
31 Oct – 7 Nov
Quick stats about 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
$152 NZD before taxes and fees
Destinations to explore
- Baltimore Holiday rentals
- Ocean City Holiday rentals
- Cape May Holiday rentals
- Wildwood Holiday rentals
- Rehoboth Beach Holiday rentals
- Arlington Holiday rentals
- Washington Holiday rentals
- Deep Creek Lake Holiday rentals
- Philadelphia Holiday rentals
- Jersey City Holiday rentals
- New York Holiday rentals
- The Hamptons Holiday 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 a patio Shady Side
- Monthly Rentals Shady Side
- Rentals with outdoor seating Shady Side
- Rentals with a washing machine and dryer Shady Side
- Family-friendly rentals Anne Arundel County
- 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