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

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.

Romantic, hot tub, king bed, private, pet-friendly
Uniquely spacious escape for couple, small family, or solo traveler. 30-foot great room, wall of windows facing large deck, oak floors NEW HOT TUB in private setting. King bedroom with en suite bath; loft has twin bed. Modern with touches of mcm & vintage create a magical retreat for you in the treetops. On 2 acres. Hike to top of Cacapon Mountain from back door. Quick drive (3 mins) to private community pool/hot tub/tot pool (summer only). 10 minutes to Berkeley Springs with Roman Baths, arts s

Bird's Eye View
Nestled high amidst the sturdy branches, "Bird's Eye View" is a sanctuary suspended between earth and sky. Located less than 5 minutes from Deep Creek Lake and perched among the foliage, our treehouse offers a panoramic perspective of the surrounding forest, granting its visitors an unparalleled vantage point to observe nature's wonders. Relax in the hot tub and take in an amazing sunset. The home is a harmonious blend of locally-crafted art and furniture to add rustic charm and modern comfort.

Hot tub, Playground, Fire pit, View and Game room
Escape to our cozy 3-bedroom, 3.5-bathroom cabin located on a serene mountain. With a game room featuring arcade games, a racing simulator, and foosball table, stunning sunsets, and space for up to 8 guests, it's the perfect spot for family or friends gatherings. Just 2 hours from the DC metro area, this secluded retreat offers a unique view in Northeast. You'll love the two working spaces, EV charger, treadmill, and now, the added luxury of a hot tub. Unplug and unwind in this mountain haven.

Mary's Cabin
Nestled on 2 acres in the woods of West Virginia, kick back and relax in this quiet, chic cabin. Soak in the oversized copper tub, read on the porch swing, or cuddle by the electric fireplace. All the amenities of home, but away from the hustle and bustle of daily life. Only 25 minutes to quaint Old Town Winchester, where there are unique shops, breweries, restaurants and history! The cabin is located 20 minutes from a variety of scenic hiking trails that provide opportunities for adventure.

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.

Whiskey Acres | Modern Cabin w/ Hot Tub, Axes, etc
Nestled amidst the trees, Whiskey Acres is the perfect place to escape the stresses of daily life and immerse yourself in the tranquility of nature. Situated on a wooded lot that offers plenty of privacy and space to explore; you'll love spending your days hiking the woods, tossing axes in the axe throw area, relaxing in the hot tub or simply lounging on the spacious decks. Whether you're looking for a romantic retreat or a fun-filled family getaway, you'll love your stay. 4WD recommended.

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.

1832 Historic Washington Bottom Farm Log Cabin
Welcome to our renovated 1832 Log Cabin on the grounds of the George William Washington and Sarah Wright Washington 19th century plantation. The cabin was the first structure built. Then came barns and slaves’ quarters (no longer standing). The dairy barn is now a woodworking shop and the bank barn was recently restored. The main house, built in 1835, is Greek Revival style. Today, our 300+acre is Certified Organic. We border the South Branch of the Potomac River. It’s ALMOST HEAVEN !

Glamping in a Creekside Aframe
This cozy aframe is a perfect glamping getaway for two! You'll stay on 20 acres with over 700 feet of frontage on Abrams Creek. Ready to unplug? The aframe is completely off grid with solar energy and a wood-fired stove. Sleep in luxury with fine linens and a queen size bed, but spend your day splashing in the crystal clear creek and hiking through the forest. Enjoy your evening playing cornhole while dinner cooks on the grill, topped off with a favorite beverage around the campfire.

Ridge top tiny house - mountain side views
Reconnect with nature in this unforgettable tiny house. Perched on the top of a ridge offers great views of the mountains. Modern contrasting interior with the charm only a tiny house can bring. The mountains from three different states (PA, MD, WV) can be seen from within the tiny house. Sitting on the edge of 275 acres of farmland means you will be sure to hear the turkeys gobble during the daytime or the whippoorwill at night. Relax and enjoy the scenery from the loft bed.

Walk in the clouds Cabin
Amazing veiws! This cozy cabin over looks the Potomac river valley and Greenridge state forest. You can see mountain ranges from 3 different states. Enjoy the wilderness of West Virginia with only a short drive from, D.C. and Baltimore. Just 13 miles from Berkeley springs and famous PawPaw tunnel. Perfect couple getaway. Have a bigger family? Check out our sister cabin "Hummingbird Ridge" right down the road or book both. We look forward to having you on the mountain!
Popular amenities for Western Maryland family-friendly rentals
Family-friendly home rentals with a hot tub

Sleeps 6, 2BR, 3BED, FREE Shuttle, POOL, Hot Tub

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

Cottage at Lost River Ridge

Pets? YES! Hot Tub | Fast Wi-Fi | Fire Pit

Charming log cabin by Berkeley Springs (+ hot tub)

Winter Escape | Hot Tub, Sauna, King Bed & Pets

The Sanctuary

Eagles Nest Treehouse w/HOT TUB & a VIEW
Family- and pet-friendly home rentals

Spruce Run Cottage, Farm stay on Catoctin Mountain

Seclusion-Escape to this Cozy Getaway in the Woods

Hummingbirds Hideaway Treehouse

Rustic Cabin on Cacapon River for Private Getaway

Secluded two bedroom cabin on 5 acres

The Shadoe on Greene

Easygoing

Sugar Maple Chalet - 67-Acre Farm
Family-friendly home rentals with a pool

Hidden in Shenandoah Valley|Pool|Pets|Fire Pit

Cedar Loft at The Woods-Vintage Chic Cabin Retreat

Winter Escape? Coffee bar, fire-pit, stargaze!

Mountain & Lake Retreat: 2x Queen, saltH2O Hottub

All Seasons Retreat - Screened Porch - Fire Pit

New! The Butterfly Suite at Enchanted Table Meadow

Five Oaks Cabin at The Woods Resort

Seven Springs *Ski-in/out Condo 1 Bed.(king),1 Bth
Destinations to explore
- New York City Holiday rentals
- Western North Carolina Holiday rentals
- Greater Toronto and Hamilton Area Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Mississauga Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Grand River Holiday rentals
- Jersey City Holiday rentals
- Campsite rentals Western Maryland
- Rentals with an EV charger Western Maryland
- Rentals with a washing machine and dryer Western Maryland
- Flat rentals Western Maryland
- Rentals with a firepit Western Maryland
- Townhouse rentals Western Maryland
- Pet-friendly rentals Western Maryland
- Boutique hotels Western Maryland
- Rentals with pools Western Maryland
- Tiny house rentals Western Maryland
- Cottage rentals Western Maryland
- Rentals with outdoor seating Western Maryland
- Rentals with a cinema Western Maryland
- Rentals with a sauna Western Maryland
- Rentals with lake access Western Maryland
- Rentals with a patio Western Maryland
- Bed and breakfasts Western Maryland
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- Fitness-friendly rentals Western Maryland
- Apartment rentals Western Maryland
- Hotel rooms Western Maryland
- Rentals with a hot tub Western Maryland
- Waterfront rentals Western Maryland
- Chalet rentals Western Maryland
- Rentals with a fireplace Western Maryland
- Smoking-friendly rentals Western Maryland
- Cabin rentals Western Maryland
- Guest house rentals Western Maryland
- Rentals with a kayak Western Maryland
- Rentals with breakfast Western Maryland
- Farm stay rentals Western Maryland
- House rentals Western Maryland
- Ski-in/ski-out rentals Western Maryland
- Family-friendly rentals Maryland
- Family-friendly rentals United States
- Wisp Resort
- Fallingwater
- Timberline Mountain
- Seven Springs Mountain Resort
- Idlewild & SoakZone
- White Grass
- Ohiopyle State Park
- Canaan Valley Resort & Conference Center
- Laurel Mountain Ski Resort
- Canaan Valley Ski Resort
- West Virginia University
- Rock Gap State Park
- Tygart Lake
- Swallow Falls State Park
- Coopers Rock State Forest
- Laurel Hill State Park
- Fort Ligonier
- Green Ridge State Forest
- Laurel Ridge State Park
- Deep Creek Lake State Park
- Fort Necessity National Battlefield
- Smoke Hole Caverns




