Family-friendly holiday rentals in Western Maryland

Cabin on Middle Creek - Myersville MD - Middletown

Park the car & walk across the creek on the foot bridge to serenity along Middle Creek. Nestled between South Mountain State Park & Gambrill State Park, lies a beautiful & relaxed 9-acre private cabin retreat. Great place to unwind & de-stress. Let the sound of the creek or rain on the tin porch roof put you to sleep at night. It has all the essentials of home. Enjoy the fire pit on cool evenings or take a dip in the stream on a warm day. The cabin offers a perfect peaceful or romantic setting

Sleepy Hollow Log Cabin

Sleepy Hollow Log Cabin at Beechnut Springs is nestled in the majestic Blue Ridge Mountains. A short distance from Rt 70 as you travel down scenic route 17 following a bustling trout stream to Beechnut Springs entrance. After you arrive & settle into your secluded cabin, you will find many unique activities & quiet places in this serene setting amid the wonders of quiet waterfalls, easy walking paths, a wildlife haven, natural running streams & "The Bog Shack". Welcome to Sleepy Hollow Log Cabin

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.

Mountaintop Cabin w/ Outdoor Tub

Come unwind at our mountaintop cabin! Whether it’s the (new cast iron) soaking tub on the back porch, the two hammocks, our giant firepit, or the comfy king bed in the loft, you’ll want to sit, sip, snuggle and tell tall tales as the sun sets and stars shine. Second small bedroom doubles as an office. A gas stove twinkles inside while an antique spiral staircase adds elegance. Fully-equipped kitchen, laundry, and Starlink to provide top-tier connectivity. We’re kid friendly and dog positive too!

Rustic Cabin on Cacapon River for Private Getaway

Rustic, 100+ year old primitive mountain cabin in West Virginia along the Cacapon River. Beautifully restored with wood stove, loft, & screened in porch. Access to 214 acres of private mountain land & over 1/4 mile of river frontage plus 1/2 acre pond, trails, and private shooting range. This cabin is 1-room and completely off grid. It has NO electricity or plumbing/running water, but does have a Porta-John serviced weekly. Renter will be cabin camping so pack accordingly; tents also welcome.

Blue Mountain Hideaway • Enchanting Glamping Stay

Unplug and unwind at Blue Mountain Hideaway, a boutique glamping tent nestled in the woods near Shenandoah National Park and the Shenandoah River. Enjoy a real bed, a fully equipped outdoor kitchen, and complimentary firewood. No WiFi, no distractions, just the sounds of nature. Cozy up by the fire, savor slow mornings, and reconnect with what matters most. Just bring your cooler and clothes, we’ll handle the rest. Perfect for couples, solo travelers, and anyone craving a quiet place to reset.

Rooster Wrest in the Trees

Sweet 2 bedroom bungalow. Cozy, ideal for lovers, or a quiet beautiful somewhat rustic retreat environment. Rooster has 1 full bath. Living room with satellite TV, Netflix; wood burning stove fireplace, wood provided, fully equipped kitchen, dining table, linens and starter paper goods furnished. Large deck and screen porch looking out on Cacapon Mountain. Hot tub off master bedroom deck in trees, feels like a tree house. Many mornings mist rises up from river, half mile away as crow flies.

Log Cabin

The primary bedroom features a queen-size bed, while the secondary bedroom includes a full-size bed. The living area is equipped with a sleeper sofa for extra sleeping space, and the loft adds two twin mattresses for additional accommodations, ideal for kids. The cabin’s kitchen is equipped with everything you need, including an oven and refrigerator and microwave. Whether you're enjoying time indoors or exploring the outdoors, this cabin offers the perfect balance of comfort and 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.

❤️ 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 3 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.

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 !