
Family-friendly holiday rentals in Hagerstown
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Hagerstown
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Charming vintage cabin in the ❤️ of Middletown.
Cozy cabin in the ❤️ of Middletown, MD. Within walking distance to quaint Middletown restaurants, shops, & parks. Set your sights on adventure within a short drive. Enjoy downtown Frederick restaurants, shops, parks, & nightlife. Visit the local wineries, breweries & festivals. Hike the Appalachian trail. Float the Potomac River. Bike the C&O Canal. Ski the slopes @ area ski resorts. Golf 18 holes @ the championship golf course. Visit wedding venues. Go antiquing. Tour quaint nearby towns. Etc

Bear Pines Retreat ~ Game Room ~ Screened Porch
Come enjoy this 3 bedroom/2 bath A frame cabin in The Woods. Bear Pines Retreat features 2 bedrooms on the lower level with 4 beds and full bathroom. The Master Suite loft has a queen bed with mountain spa bathroom. You can connect to the built in Bluetooth speaker and play some relaxing music while looking out the skylight above. The living area has plenty of seating with wood burning fireplace and 55” TV mounted above. You can enjoy over 100 cable channels, music and streaming services.

Private, relaxing, scenic 2 bdrm unit, Sleeps 1-5
My mother said over and over again, “The most beautiful place in Washington County “. Start your day with a brisk walk on a nearly 1 mile path that surrounds the perimeter of this beautiful farmland property. Enjoy your morning coffee as you listen to the birds. Relax in a rocking chair on the gazebo as you watch the sun go down behind the mountains. Less than 10 min from I 70 and I 81 and 20 min from Whitetail Ski. Don't expect everything brand new, but expect everything to be neat and clean.

Near I-81, but private! Laundry! No fees!
Welcome to your peaceful retreat! This spacious and clean apartment features a fully equipped kitchen, dual shower heads, a cozy living area, and a washer/dryer for your convenience. Ideal for travelers seeking a quiet getaway or a stopover along I-81, our home is close to Antietam Battlefield, Hagerstown Shopping Outlets, C&O Canal, Tomahawk MotoX, Greenbrier State Park, Shepherdstown, and Harper's Ferry. Enjoy a comfortable stay with thoughtful amenities designed to make you feel at home!

Cozy West Virginia Treehouse
Thanks for checking out our treehouse! It’s 4 minutes from downtown Shepherdstown and 15 minutes from downtown Harpers Ferry. We are excited to share it with other fun-loving folks! The treehouse has heat and AC, a tiny kitchen with a mini fridge, stove top, toaster oven, gravity-fed sink and kitchenware. There’s a bathhouse built on the back of the host’s home with a conventional toilet and shower. There’s also an outhouse with a light and essentials. We provide wood for the fire pit also.

The Frame ~ Charming Nature Escape ~ Hot Tub ~ BBQ
Escape to the charming 2BR 1Bath A-frame on a secluded wooded property just 10 mins away from Shippensburg, PA. Whether you're looking to savor nature‘s tranquility from the luxurious hot tub, share stories around the fire pit, or explore picturesque Cumberland Valley, this will be the ideal starting point for your adventures! *2 Comfortable BRs *Open Design Living *Full Kitchen *Smart TV *Backyard (Hot Tub, Sauna, Fire Pit, BBQ, Outdoor shower) *High-Speed Wi-Fi *Free Parking *EV charger

Unique historic home - Springhouse 1803
If you are looking for a unique place to stay, come visit us at Springhouse 1803. Yes, there really is a spring under the house. After sitting empty for 20+ years, the house has been restored to be lived in again and it has maintained much of its colonial charm. The house has all the amenities you need for a comfortable stay. NOT A PARTY HOUSE, OWNER IS ON SITE in separate house. If you're looking for a day that is blocked, you can inquiry if it's available, see below for more details.

Creekside Retreat at the Jewel Vinsota
Relax in a quiet, curated, pet-friendly art exhibit. Live with paintings & sculptures that are for sale. This garden apartment is tucked into a hillside above a creek, along the Jewel Vinsota Sculpture Trail. Your host/gallery curators live upstairs. The “Artist’s Guesthouse” is next door. The private entrance is down a stone-stepped path. Perfect for 2 w/ the queen bed but room for 3 w/ the living room futon. Fully equipped kitchen. Private charcoal grill and fire pit next to the creek.

Cozy Secluded A-Frame Cabin Retreat
Visit us on IG @almostheavenwvcabin for the latest photos and cabin moments! Welcome to Almost Heaven Cabin, our beloved A-frame escape tucked away on a private, wooded acre in the heart of the Sleepy Creek Wildlife Management area. Surrounded by 23,000 acres of protected wilderness, this cabin was created as a peaceful family retreat from city life-yet it's just a scenic 1.5-hour drive from DC and Baltimore. Expect quiet mornings, fresh mountain air, and a true West Virginia getaway.

Spruce Run Cottage, Farm stay on Catoctin Mountain
The cottage is located on 25 acres of mostly wooded terrain off Highway 17 near Wolfsville, Maryland, less than an hour and a half from D.C. The cottage faces the woods and the private drive down to the creek. There is almost zero light pollution at night so stargazing is incredible from the balcony. The hosts live on the property up the hill in an 1890’s chink log cabin. Although you can see our house, the cottage feels very private and is a quiet comfortable retreat in the hills.

Oak Hill Private Suite Historic North End
A recently renovated private suite only 1.5 miles from town center. Welcoming ‘walking’ neighborhood of architecturally diverse homes inspired by the Garden City Movement of early 20th C. Near both Interstate 81 and 70, Museum of Fine Arts, Whitetail Ski Resort, New Baseball Stadium, Antietam, Gettysburg, Frederick, C&O bike trail, wineries, outlets. Guests enjoy stays for tourism, conferences, trainings, the MD Int’l Film Festival, JFK 50, family visits and artist retreats.

Private Country Club Home
I am an experienced super host with eight years of hosting. I have a charming mother-in-law suite with your own entrance in an upscale country club development. Features a beautiful two acre backyard, a fire pit, outdoor deck and grill, private living room, kitchen, bath, and bedroom. We are just 20 minutes from White Tail Ski Resort and less than an hour to Gettysburg, Antietam Battlefield, the Appalachian trail, and C&O Canal. Come join us for a relaxing stay.
Popular amenities for Hagerstown family-friendly rentals
Family-friendly home rentals with a hot tub

StayAround Dome ~ Unique & Tranquil Gem ~ Sauna

Abby's Lookout - Raised Retreat w/Hot Tub & WiFi

Cabin With Wood Burning Hot Tub

The Hideaway~Remote Cabin ~Hot Tub~Fast Internet!

Spectacular views, intimate dome

Waterfront Cabin on the Potomac River w/ Hot tub

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

Moss Hill ~ Cozy Cabin w/Hot Tub & Fast Wi-Fi!
Family- and pet-friendly home rentals

VIEWS! Fire Pit|River Access|Pool Table|Arcade

The Little White House

Cottage on our horse farm

the Lodge- Stunning View- Hot Tub- Dog Friendly

Country 2-Bed/2-Bath Barndominium w/Beautiful View

Round Mountn Top House! Prof. Cleaned w EV-chrger

Mountain Church Cottage

Beautiful Mansion, Pool, Fishpond & Home Theater
Family-friendly home rentals with a pool

Harmony Lodge nestled in wooded tranquility!

Cedar Loft at The Woods-Vintage Chic Cabin Retreat

Civil War Farm House w/Heated (seasonal) Pool

Wizard's Escape | Sleep15+ | 2 Escape Rooms &Pool

*Cottage @ Firefly Cellars* VA Wine Country escape

The Hunt Box @ Tally Yo Farm

The Cabin on the Run

Starcatcher Chalet, The Woods Resort
When is the best time to visit Hagerstown?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $187 AUD | $178 AUD | $190 AUD | $206 AUD | $204 AUD | $204 AUD | $239 AUD | $236 AUD | $204 AUD | $209 AUD | $206 AUD | $199 AUD |
| Avg. temp | 1°C | 3°C | 7°C | 13°C | 18°C | 23°C | 25°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Quick stats about holiday rentals that are family-friendly in Hagerstown

Total holiday rentals
Explore 40 holiday rentals in Hagerstown

Nightly prices starting at
Hagerstown holiday rentals start at $56 AUD per night before taxes and fees

Verified guest reviews
Over 2,150 verified reviews to help you choose

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Hagerstown holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Hagerstown rentals

4.6 Average rating
Hagerstown stays receive an average rating of 4.6 out of 5 from guests
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- Family-friendly rentals Washington County
- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Liberty Mountain Resort
- Whitetail Resort
- Stone Tower Winery
- Cunningham Falls State Park
- Codorus State Park
- Cowans Gap State Park
- Caledonia State Park
- Berkeley Springs State Park
- Gambrill State Park
- Cacapon Resort State Park
- South Mountain State Park
- Sky Meadows State Park
- Harpers Ferry National Historical Park
- Green Ridge State Forest
- Big Cork Vineyards
- Rock Gap State Park
- Bluemont Vineyard
- Antietam National Battlefield
- Museum of the Shenandoah Valley
- Old Town Winchester Walking Mall
- Hollywood Casino At Charles Town Races
- Catoctin Mountain Park
- Greenbrier State Park
- Dulles Town Center




