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

The Patent House
Built around 1760, our log cabin sits on our 3 acre farmette, in the countryside in view of the foothills that separate VA, WV & MD. It's fully renovated, with a master bedroom (queen) & full bath upstairs. There is a convertible sofa downstairs (full). Cabin is next door to our house & shares a fence with our pasture where our mini donkeys live. We have yappy dogs and friendly outdoor cats. We're in the country, so bugs make their appearance but they tend to go straight to the window sills.

Enchanting PET FREE W/Amazing ViewHot Tub Overlook
Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry. Quiet away from the train in old town Large patio, courtyard, firepit, hammock, outdoor 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, "Mind Blowing" soaking tub or taking in the beautiful scenery while enjoying a relaxing shower in our all cedar shower room.

Historic Scrabble, Shepherdstown
The perfect private guest cottage situated beside a beautiful historic home in the unique community of Scrabble Unincorporated just a half-mile from the Potomac River. Modern, comfortable and tastefully decorated with full amenities and parklike surroundings with an abundance of nature at your doorstep. Close to Shepherdstown / Shepherd Univeristy (12 minutes), Martinsburg (20 minutes), Harpers Ferry (20 minutes) and in the heart of civil war history including the famed Antietam National Park.

Arden House, Inwood WV
Ground level two room unit. No steps. Separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed, sofa and full refrig.. In a separate living area, there is a queen bed, TV, bathroom, desk, table, microwave, convection oven, air fryer, gas fireplace. No oven. Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic

Skoolie on Charming 40-Acre Farm
Escape to the tranquility of our converted school bus, nestled on a beautiful 40-acre farm near Charles Town and Harpers Ferry. This charming accommodation combines the novelty of a converted bus with the rustic charm of a farm. This bus features a cozy interior seamlessly blending comfort and character. Relax on the deck, enjoy meals in the full kitchen, take a dip in the hot tub and enjoy nights at the fire pit. Keep in mind, that this is camping. Bugs, smells, animals all come with that.

❤️ Secluded 1940s Romantic Tiny House on the River
Relax and escape to the peace and quiet by the Potomac river, and wake to beautiful romantic views of the river and mountains, in this romantic 200 square foot tiny house situated on 2.5 acres, 450 feet of river front land. Explore and partake of all the activities on the river and surrounding area, just 1 mile from Shepherdstown. Fish, bike, kayak, tube, or just sit by the river and watch the birds and wild life. Read by the river or in the quiet comfort of the house, w/ some wine on us.

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.

Barn Apartment in VA Wine Country
Barn apartment in the upper level of a bank barn. Fourteen miles from downtown Leesburg, 5 miles from Harper's Ferry, 1 mile from VA-9 Appalachian trail head. Close to Harper's Ferry Adventure Center, wineries, breweries, tubing, kayaking, hiking, farms. Full kitchen. Unplugged with the exception of Wi-Fi - no satellite or TV. There is cell signal. Rate includes 6% Virginia state tax and 7% Loudoun County hotel tax. 1 queen bed, 1 twin, and 1 floor mattress (pull out futon).

Cozy Cabin Hidden Away on a Lake!
MOUNTAIN MAMA VACATION HOMES The perfect getaway for any season! Enjoy the lake views inside next to a roaring fire, or in the summertime take the kids for a swim in the shallow water just off your private beach. Relax in the hot tub set in the back deck as the sun sets over the lake and the stars start to come out. Make every night movie night on the 50" 4k TV. Whether you want to stay in or see the area, this cabin has something for every member of the family!

The Log Cabin
A restored 1700's log cabin in a convenient location to Shepherdstown and surrounding attractions. One bedroom upstairs with a queen sized bed. One pull out sofa in the downstairs living area. In the summer of 2018, we have added an intimate brick patio area suitable for alfresco dining and for fireside sitting. It is peaceful. It is beautiful. You will not want to leave.

Last Rodeo Cottage
Our cottage is private where guest can relax; Looking to spend some quiet time out of the city. Close to D.C.and the Historic site of surrounding areas. Close to Charlestown Casinos. Our home is right off I- 81 This cottage is Handicap accessible from private parking to shower and amenities. Lovely park like setting shared with our family pets.

Your own "Tiny House"
Private, furnished studio apartment. Country setting with easy access to all major highways in Frederick, MD. Convenient location for day trips to Washington, DC, Gettyburg, Harpers Ferry, Baltimore. Private bathroom. Fully furnished kitchen. Transportation can be arranged to pick up/drop off for AT and C&O Canal hikers.
Popular amenities for Charles Town family-friendly rentals
Family-friendly home rentals with a hot tub

Blueridge Mountain Retreat Apartment

StayAround Dome ~ Unique & Tranquil Gem ~ Sauna

Hot Tub, Wi-fi, Rural Setting, Smrtv, Convenient

Whiskey Acres | Modern Cabin w/ Hot Tub, Axes, etc

The Wizard's Chalet • Cozy nature escape • Hot Tub

Luxury Mountain Getaway: Sunsets, Wines & Views.

Harpers Ferry Hideaway - Cabin w/ Hot Tub, Pond

Family & Pet Friendly- Hot Tub-Full Kitchen
Family- and pet-friendly home rentals

Mary's Cabin

Eclectic & Romantic - Walk to Historic Downtown!

Applemoon: Charming Log Cabin in a Mountain Lake Community

Spruce Run Cottage, Farm stay on Catoctin Mountain

Five Oaks Cabin at The Woods Resort

Rustic and stylish mountain getaway

Historic Wisteria House on Old Town Walking Mall

Stone School House - Minutes from Harper's Ferry
Family-friendly home rentals with a pool

Hidden in the Valley | Pool | Pets | Fire Pit

Harmony Lodge nestled in wooded tranquility!

Cedar Loft at The Woods-Vintage Chic Cabin Retreat

Bear Pines Retreat ~ Game Room ~ Screened Porch

Cozy A-Frame Cabin In The Woods

Beautiful 2BR/1BA Renovated Condo near DC

The Cabin on the Run

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool
Quick stats about holiday rentals that are family-friendly in Charles Town
Total holiday rentals
Explore 20 holiday rentals in Charles Town
Nightly prices starting at
Charles Town holiday rentals start at £52 per night before taxes and fees
Verified guest reviews
Over 1,410 verified reviews to help you choose
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 of Charles Town holiday rentals include wifi access
Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Charles Town rentals
4.8 Average rating
Charles Town stays are highly rated by guests – averaging 4.8 out of 5!
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