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.

0 of 0 items showing

1 of 3 pages

Top guest favourite

Guest suite in Capitol Hill

4.99 out of 5 average rating, 325 reviews

Neighborhood Home near Capitol Hill Park Free, Walk to Metro

Park your car in a free off-street parking spot and walk or take the metro from this charming English basement with plenty of natural light. Stylishly simple, classic design is enhanced by exposed brickwork, and homey touches. Automatic booking is limited to 30 days, but feel free to contact us about booking a longer stay. Guests have their own private one bedroom with a full bath, living area and kitchenette. Free off street parking is available for small and medium sized cars. You will have complete privacy and use of the suite which is in our sunny basement. You will have your own entrance accessible by touchpad. We provide each reservation with a unique key code to unlock the door and control the alarm. We are available if you need us, but otherwise you probably won't see us. The home is in a residential neighborhood on the eastern side of Capitol Hill, a 30-minute walk from the Capitol and a short 10 minute walk to the metro, buses, bike share, and Zipcars. Buy food and flowers at the historic Eastern Market, or dine out at Barracks Row. You can reach the Capitol by foot (30 minutes) or Uber (under 10 minutes), but many visitors use the subway system, called the Metro. The Stadium Armory metro stop is about six blocks away (less than 10 minutes walk) and is on the blue/orange/silver line which takes you directly to the Capitol (Capitol South stop), Museums (Smithsonian stop) and the White House (Metro Centers stop). Of course the Metro will also take you to virtually any other location you hope to visit. There is also a bus stop one block away where you can catch the bus to the historic Union Station located right next to the U.S. Capitol. From Union Station you can walk to the Mall, get the metro, even take a train to your next Amtrak destination. Some guests use the "Circulator" bus which runs a loop around the Mall. You can buy a daily pass at Union Station to hop on and off the Circulator throughout the day. We we also have a bike share and zip car spot within a few blocks. Check-in is at 4, but we accommodate earlier check or luggage drop off whenever possible.

Superhost

Flat in Annapolis

4.88 out of 5 average rating, 288 reviews

Gybeset Eastport Inn

Enjoy exclusive use of this boutique hotel-styled upstairs apartment in a beautifully restored 1930s craftsman-style building in the heart of Eastport. Private off-street parking. Short walk to downtown Annapolis. Just a few doors away from one of the hottest restaurants in Annapolis, Vin 909. A seasonal farmers' market is located across the street along with restaurants and other amenities. Hotel-like services available for longer stays. Fully licensed by City of Annapolis for AirBnb operation.

Top guest favourite

Guest suite in Arnold

4.96 out of 5 average rating, 672 reviews

Old Bay Bungalow

This in-law apartment located in the lower level of my occupied home is just moments outside of Annapolis, mere blocks from the Magothy River. I enjoy inviting guests into the space, and take pride in treating new friends like family. Come rest your weary bones in your private retreat with its own separate entrance, relaxing sunporch, and stocked kitchenette. Reach into the fridge and enjoy cold soda or a local beer on me! Sit around our fireplace and relax. Settle into the Old Bay Bungalow!

Guest favourite

Flat in Annapolis

4.92 out of 5 average rating, 101 reviews

Dazzling day/night water views,1st class amemities

TREAT YOURSELF! YOU DESERVE THE VERY BEST! HUGE DISCOUNTS FOR WEEK AND MONTH LONG STAYS! Treat yourself to the good life while in Annapolis! Gorgeous 14yr. old custom designed & furnished 1470sq.ft. waterfront apartment, 9ft. ceilings, fantastic water views day & night! Private pier, firepit and 40ft. waterfront covered patio for guests use. Guest parking for 4 cars. Few minutes to US Naval Academy, Annapolis Harbor, restaurants, shopping. Pet-friendly, must be cleared with host. *see below*

Top guest favourite

Guest suite in Chestertown

4.99 out of 5 average rating, 226 reviews

Beautiful Waterfront Chestertown Getaway

Lovely three room waterfront guest suite conveniently located less than 10 minutes from historic Chestertown and Washington College. Beautiful views of our tidal creek, full kitchen, wooded lot, quiet neighborhood, bird watching, kayaking, great biking & running options. Friendly pets (indoor cats and dogs who can share the yard with us and our dog) are welcome. We donate 5% of proceeds to Kent Attainable Housing, the Animal Care Shelter of Kent County or ShoreRivers conservation—your choice.

Superhost

Home in Edgewater

4.76 out of 5 average rating, 293 reviews

Edgewater/May Getaway!

Charming, spacious single-family home in the heart of Mayo, perfect for families or groups. Comfortably sleeps 6 with space for up to 8 guests. Enjoy a modern, clean design and plenty of room to unwind. Relax in the cozy sunroom or soak in the hot tub overlooking the serene, park-like backyard. Fully equipped with all essentials for a hassle-free stay. Just minutes from Edgewater, 10 mins to historic Downtown Annapolis, 25 mins to Baltimore, and 30 mins to DC. Parking in driveway/garage only.

Guest favourite

Guest house in National Harbor

4.93 out of 5 average rating, 741 reviews

Urban Cottage,MD minutes from DC/National Harbor

Come and enjoy our spacious detached cottage,lounge on your private back deck overlooking private parkland forests. A real urban escape in an excellent location! Just a few blocks away from the MGM Resort / Casino, National Harbor, and shopping. Across the river from historic Alexandria and 10-minutes from Washington,DC. Great for a solo adventure,couples,and friends (up to 4 guests). Enjoy the seasonal steam house and personal wood-burning stove if you book in the cold months.

Guest favourite

Guest house in Galesville

4.95 out of 5 average rating, 172 reviews

Nautical Charm and relaxing waterview!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

Top guest favourite

Home in Deale

4.99 out of 5 average rating, 146 reviews

Chesapeake Waterfront-Kayaks-Crab-Fish-FirePit-Spa

There's nothing like being directly on the water! Relax and rejuvenate in this Chesapeake waterfront estate home which includes private pier, hot tub and fire pit. Crab or fish off the pier or take the kayak out to see the Chesapeake bay wildlife. Try out paddle boarding! Sit around the fire pit at night or watch the stars at night while soaking in the hot tub. Make wonderful memories. Great place for families and multi family groups.

Top guest favourite

Home in Lusby

5 out of 5 average rating, 141 reviews

Historic Rousby Hall, Waterfront, Pool, Beach

Rousby Hall is located on the Patuxent River, outside of Solomons Island with a view of the river's opening to the Chesapeake Bay. The 16-acre property is adjacent to our very private conservation area that borders our 300-foot private beach. The year-round property has a pier, and in-ground pool (May-October) with amazing river views. Also hosts weddings+events up to 100 guests (additional event fee applies).

Top guest favourite

Cottage in Deale

4.82 out of 5 average rating, 182 reviews

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Savor our three-bedroom Cottage in this peaceful western shore spot, enjoy two acres of green space, the pier, kayaks, swings, fire pit, shady lawns & sun-drenched loungers, local waterfront dining or eat in, close to Washington, D.C., Annapolis, & Baltimore at this honeymoon-worthy country-like micro-resort. Due to the current COVID-19 situation, we have offered SPECIAL discounts for longer-term rentals

Top guest favourite

Guest suite in Edgewater

4.9 out of 5 average rating, 518 reviews

South River Park Apartment

Located minutes from Annapolis, the in-law apartment offers access to Baltimore and DC in under an hour. The apartment offers its own entrance, full kitchen, one bathroom, one bedroom, tile floors, pullout sofa, Wifi, and parking. The apartment is registered with the Anne Arundel County Dept. of Inspections & Permits, #STR-15, for short term rentals.