Cabin holiday rentals in Winchester

The Bella Vista House

This modern cabin offers a beautiful view of the Shenandoah Valley and is a perfect getaway home! To experience an unforgettable moment on the porch, make yourself a cup of coffee and enjoy peace and tranquility. Inside you will find an open floor plan with soaring ceilings, a well-stocked kitchen and an amazing wall of windows! Minutes from the Shenandoah River (w access to road boat ramp), Shenandoah National Park, Skyline Drive, wineries, river sports, horseback-riding, Luray Caverns & more.

Riverhouse, HOT TUB Mid Century COZY RIVER Escape!

~Break FREE and lift your soul at Riverhouse! Sleeps 5 and only a 60 min drive from Washington, DC and NOVA! Picture HOT TUB relaxation with FRONT ROW RIVER VIEWS, serene privacy, and an eclectic, unforgettable vintage vibes~ Whether relaxing on your private deck or in the NEW hot tub, let the river carry your worries away and the fresh air bring you back to life! To energize, decompress, release your inner creativity, or fall in love ~for the first time or over again, choose Riverhouse!

Trout Run at Lost River A-Frame Cabin

This is our gorgeous private A-Frame cabin in the middle of nowhere, deep in the West Virginia mountains. On 6+ acres with roaring stream, just a 3 min drive to the lake, 2 hours from DC / Baltimore. - The A-Frame cabin style is very unique - Sit/Stand desk w/ 27" 4k monitor - 46" TV w/ roku ultra & blu-ray - Game table w/ board games - Ping Pong table & Darts - Nintendo 64 on CRT TV with Smash Bros & Mario Kart - Super dog friendly - Fire pit, grill & BEAUTIFUL stone fireplace - 12 mbps Wifi

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.

The Nest: Modern Cabin Retreat on 5 Wooded Acres

Welcome to The Nest, a light‑filled, chalet‑style cabin tucked into 5 wooded acres. A short drive from Berkeley Springs, Harpers Ferry, and Cacapon State Park, it’s your base for hot springs, hiking, trails, and small‑town restaurants. By day, explore paths, wineries, and historic main streets. By night, come “home” to star‑studded skies, mountain views, and wildlife. With fast Wi‑Fi, a workspace, and a fully stocked kitchen, The Nest is perfect for families, couples, and remote workers.

West Virginia's only Airbnb Luxe Property

IG @montevistawv Luxury Getaway Professionally Designed for STR 🏔️Massive Panoramic 3 State View 🏌️‍♂️Golf Ball Driving Range 🏀 Pickleball, Basketball, Volleyball & Tennis 🎮 PlayStation 5 Mini Disc ♨️ 6-Person Hot Tub 🔊Sonos Sound Throughout 🔋Level 2 EV Charger 🥾 Hiking Trail on site 🌳 33 private acres, no quiet hours 🔥 Massive Firepit + Grill & Pizza Oven 🛋️ Cozy Gas Fireplace 🌐 Fast WiFi & Three 65" Smart Tvs 🛏️ 3 King Beds & Twin Bunk Bed 💼 Dedicated Work Area

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

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

Wilderness Ridge | Private Cabin w/ Mountain Views

"Wilderness Ridge" is the perfect private refuge to soak in the stunning views of the Shenandoah Valley while spending time with friends and family. The cabin features a full kitchen, theater room, and propane fireplace. The home’s location lets you tour local vineyards less than five miles away, or visit the famous Apple House for apple cider donuts. As night falls, return home for a BBQ on the deck while the sun sets over the valley and mountains below!

Foxtrot Mokki | Secluded Getaway 2 Hours from DC

Welcome to The Foxtrot Mokki—a Nordic-inspired retreat just two hours from DC and Baltimore. Solitude is signature. Nestled on seven secluded acres with rain-fed streams, our cozy cabin is designed for tranquility and connection with nature. Located between Old Town Winchester, VA, and Berkeley Springs, WV, it's the perfect outpost for exploring the Northern Shenandoah Valley—from charming towns to scenic hikes and wineries.

Mountain Top Cabin

Sit for a spell around the campfire or catch your breath on the deck, we’re sure you’ll fall in love. Located on the top of the mountain, you'll have beautiful views of sunrise and sunset. We have a peaceful location where you can bird watch and see wildlife and Mother Nature in her glory. There is a beach at the swimming pond and a stocked fishing pond available to use so bring your beach chair and fishing gear.

Mountaintop Retreat with Wood Fired Hot Tub

Doah House is a private retreat perched on a bluff atop the Blue Ridge, with wide views over the Shenandoah Valley. A calm container for rest and observation, the pace softens, shaped by small rituals: lighting the fire, soaking in the wood-fired tub, making coffee by hand. Weather moves through the trees, changing the light, the air, the sound. Each day feels different. The forest shifts, and you might, too.

Cozy Log Cabin w/views + Hot Tub near Shenandoah

This unique home combines all the best that the Blue Ridge Mountains have to offer. A cozy and rustic log cabin, amazing mountain-top views, easy access to hikes and river activities (either state or national parks), and the best wineries in the area! It's the perfect mix of simple mountain living, but with all of the modern amentities you could want for a comfortable stay. New hot tub was just added.