
Cabin holiday rentals in Winchester
Find and book unique cabins on Airbnb
Top-rated cabin rentals in Winchester
Guests agree: These cabins are highly rated for location, cleanliness and more.

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 Chalet Near Berkeley Springs & Harpers Ferry
The Nest is a chalet-style cabin tucked into the tree-lined mountains of Berkeley County, WV. It offers adventure, a quiet retreat & good family fun. With 5-acres in the mountainside, you'll enjoy star studded skies on clear nights & wake up to birds singing & deer wandering, with mountain views through vaulted windows. The Nest is near Martinsburg, Berkeley Springs, Harpers Ferry, Shepherdstown, Charles Town & Cacapon State Park, among other go-to destinations on the Eastern Panhandle.

New! 30 mins to SNP! Water views! So cozy! - RR
★Beautiful setting only 30 mins from the Park ★Cabin built 2023 ★Hot tub and deck w/ lake view (no water access) ★Sleeps 4 (2 more children with sofa + foldable mattress ok) ★Outdoor area w/ views ★Fire pit ★Fireplace (electric) ★Walk to river & Shenandoah Outfitters-rafting, kayaking, boating, fishing ★Smart TVs ★Games ★Reliable WiFi ★Use your own streaming ★Dining area for 4 ★Stylish & upscale ★8 minutes to Bixler's Ferry Boat Launch ★20 mins - Luray ★30 mins - Shenandoah National Park

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 !

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!

Shenandoah Twilight | Hot Tub + Sunset Views
Shenandoah Twilight is a hidden gem just 80 minutes from DC for peaceful mountain getaways, sunset views, and slow evenings in the hot tub. Spend your days hiking, wine tasting, exploring Skyline Drive, or visiting nearby Front Royal, then come back to a comfortable cabin with a fully stocked kitchen, king bedroom, fast WiFi, private hot tub, fire table, and quiet outdoor spaces. It’s an easy place to unwind, reconnect, and enjoy the beauty of the Shenandoah Valley.

Rustic and stylish mountain getaway
The Little Black Cabin is everything you've been dreaming about for your cozy mountain getaway! Take in sweeping views, curl up by the fireplace, or make s'mores at the fire pit. Whip up a gourmet meal in the small but well-appointed kitchen. Three dining areas offer options for dinner -- or a remote office, thanks to wifi. Sample nearby hiking, yoga, and farmers' market. We're a little rustic (no TV, AC, microwave, laundry or dishwasher) and a lot stylish!

Cabin With Wood Burning Hot Tub
Escape to our modern cabin on 12 private acres. Unwind in the wood-burning hot tub, embracing the surroundings and stars at night. With a contemporary design and natural light, this retreat blends with nature. Explore private trails throughout the property, enjoying nature and the fresh air. Inside, find comfort in the fully equipped kitchen and cozy living area. Perfect for a peaceful getaway, our secluded home provides privacy and relaxation.

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.

The Sparrow Luxury A-Frame w/Hot Tub in Shenandoah
Escape to The Sparrow, a newly built luxury A-Frame nestled in Virginia’s Shenandoah Valley, just a scenic drive from DC. This modern retreat features an African-inspired design, two bedrooms, a full kitchen, a fireplace, a private hot tub, a deck, a workspace, 4K TVs, and a PlayStation 5. Minutes from Luray Caverns, Skyline Drive, and Shenandoah National Park, it’s the perfect base for unforgettable adventure and relaxation.

COZY River Cabin + HOT TUB + Swanky, Sexy, FUN!
Have fun at Starlight on the River! Chill vibe with high style and sexy romance! ***Hot tub and river views*** Pop meets mid-mod design, modern cabin meets urban flare! The most perfect one bedroom, hot tub, riverfront Airbnb you will find, only 60 minutes from Washington DC! From life size tigers to real eagles flying by, Starlight will be a memory to never forget! ~Treat Yourself to Starlight, You Deserve This! ~
Popular amenities for Winchester cabin rentals
Cabin rentals with a hot tub

Beau Ridge Cabin (Little Cabin with a big view)

Chalet in the Orchard; Romance, Luxury, Relaxation

Modern Eclectic Treetop Cabin ~ Hottub ~ Romantic

The Cozy Bear Cabin | Hot Tub, Fenced Yard, Games

Moss Hill ~ Cozy Cabin w/Hot Tub & Fast Wi-Fi!

Private Spa Retreat in the Mountains~Sauna-Hot tub

25% Off ~ Hygge mountain retreat w/ stunning views

Riverfront Sauna! Hot Tub! Luxury Romantic Retreat
Pet-friendly cabin rentals

Unique Gem: Cozy A frame cabin in the woods

Design-forward cabin in the woods

Cedar Creek Cabin

Island cabin

Double Spur Outfitters' Brown Cabin

The Grape Escape - A-Frame Cabin in Wine Country

Cozy Historic Cabin w/ stellar view of Big Schloss

Bison Farm - Cabin "Brisa"
Private cabin rentals

Shenandoah Riverfront Cabin - Eagle Sightings

Horizon | Hot/Cold Tub, Fireplaces, Sauna, EV Plug

Creekside A-Frame on Lost River | Hot Tub | Creek

Cozy Secluded A-Frame Cabin Retreat

The Log Cabin

The Vale at Será - Modern Retreat w/Hot tub +Sauna

New! Zen Cabin in the Clouds

Ascent at Lost River (cozy cabin with views)
Destinations to explore
- New York City Holiday rentals
- Philadelphia Holiday rentals
- Washington Holiday rentals
- Columbus Holiday rentals
- Pittsburgh Holiday rentals
- Ocean City Holiday rentals
- Cleveland Holiday rentals
- Virginia Beach Holiday rentals
- Raleigh Holiday rentals
- Niagara Falls Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Rentals with a washing machine and dryer Winchester
- Cottage rentals Winchester
- Fitness-friendly rentals Winchester
- Hotel rooms Winchester
- Rentals with a fireplace Winchester
- Rentals with pools Winchester
- Rentals with breakfast Winchester
- Family-friendly rentals Winchester
- Pet-friendly rentals Winchester
- Rentals with a patio Winchester
- Condo rentals Winchester
- Apartment rentals Winchester
- House rentals Winchester
- Rentals with outdoor seating Winchester
- Cabin rentals Virginia
- Cabin rentals United States
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Berkeley Springs State Park
- Jiffy Lube Live
- Harpers Ferry National Historical Park
- Cunningham Falls State Park
- Cacapon Resort State Park
- South Mountain State Park
- Rock Gap State Park
- Whitetail Resort
- Shenandoah River Outfitters
- Reston Town Center
- Hollywood Casino At Charles Town Races
- Sky Meadows State Park
- Green Ridge State Forest
- Gambrill State Park
- Greenbrier State Park
- Bluemont Vineyard
- Antietam National Battlefield
- Weinberg Center for the Arts
- Skyline Caverns
- Dulles Town Center
- Big Cork Vineyards





