
Cabin holiday rentals in Winchester
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Top-rated cabin rentals in Winchester
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The Bird's Nest - Cabin by the River
Located on one of the Seven Bends of the Shenandoah River, the Bird’s Nest is a brand new, custom built 800 square foot cabin featuring an open loft with king bed and skylights, steam shower, heated bathroom floor, and gas fireplace. Exterior amenities include a hot tub, gas grill, gas fire pit table, fire pit by the river, and private river access in a peaceful, wooded setting. Kayaks/tubes are available to use to float down the river with the unique ability to park/exit on the hosts’ property.

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.

New Modern Cabin with Hot Tub & Arcade | HH
★30 minutes to the National Park ★Built 2024 ★Walk to Shenandoah River Outfitters ★Great amenities! ★Sleeps 6 (2 on inner spring futon) ★Outdoor areas w/ WINTER VIEWS ★Fire pit ★Fireplace (electric) ★55" Smart TVs in family room, BR1, and BR2 ★BR3 w/ arcade games ★WiFi (faster and more reliable than most in the area) ★Use your own streaming ★Dining area for 4 + bar stools for 2 ★Stylish & upscale ★8 minutes to Bixler's Ferry Boat Launch ★20 mins - Luray ★30 mins - Shenandoah National Parke

Cozy Chalet Near Berkeley Springs & Winchester
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.

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 !

Blue Ridge Retreat 2 w/ Hot Tub/Sauna/Cold Plunge!
BNB Breeze Presents: Blue Ridge Mini Lux Retreat 2! Experience the Shenandoah Valley and the beauty of the Blue Ridge Mountains from our newly-built retreat! With a private hot tub, sauna, fire pit and cool pool, the only thing that makes this retreat better is the incredible and picturesque views of the Blue Ridge Mountains that you get with your personal retreat in paradise! Your extensive amenity list includes: • HOT TUB! • Sauna • Fire Pit • Cool Pool • Grill • Picturesque Views

Cozy Secluded A-Frame Cabin Retreat
Visit us on IG @almostheavenwvcabin for the latest photos and cabin moments! Welcome to Almost Heaven Cabin, our beloved A-frame escape tucked away on a private, wooded acre in the heart of the Sleepy Creek Wildlife Management area. Surrounded by 23,000 acres of protected wilderness, this cabin was created as a peaceful family retreat from city life-yet it's just a scenic 1.5-hour drive from DC and Baltimore. Expect quiet mornings, fresh mountain air, and a true West Virginia getaway.

Kona’s Cabin • Fireplace, King Bed, Pets Welcome
🌲 Welcome to Kona’s Cabin — Your Cozy Shenandoah Escape Unplug, unwind, and settle into Kona’s Cabin, a private and pet-friendly retreat just minutes from Shenandoah National Park, historic downtown Winchester, hiking trails, wineries, and breweries. The cabin features an open living area, cozy fireplace, and a well-equipped kitchen for all your cooking needs. Kona’s Cabin is a cozy abode that’s perfect for couples, solo travelers, or a peaceful weekend getaway with your pup 🐾.

Monte Vista~Golf~Views~PS5~Sport Court~EV Charger
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!

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!

Shenandoah Twilight - Cozy Cabin with hot tub
Escape to "Shenandoah Twilight," a cozy cabin retreat perfect for couples or small families in the heart of the Shenandoah Valley. Relax in the cozy living room with a 50" TV, electric fireplace, and plush seating. Unleash your culinary creativity in the fully equipped kitchen, and dine indoors or on the patio, where breathtaking sunsets await. Unwind in the outdoor hot tub surrounded by nature’s beauty, making this cabin the ultimate serene getaway.
Popular amenities for cabin rentals in Winchester
Cabin rentals with a hot tub

Vintage Riverfront Log Cabin “Emma” w/hot tub

The Gramophone - Romantic Valley Retreat

+ The Cabin + @CPP - Hot Tub- Dog Friendly- View

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

Modern Cabin: Hot Tub, Arcade, FirePit, Pets+Pool

Rivah Retreat, HotTub~Firepit-Fishing-Deck-Private

Riverfront Sauna! Hot Tub! Luxury Romantic Retreat

The Bella Vista House
Pet-friendly cabin rentals

Design-forward cabin in the woods

Venture Cabin in Shenandoah Valley

Hottub with Valley Views ~ Romantic, Cozy

Cedar Creek Cabin

Beautiful mountain cabin, lake, recreational areas

Wilderness Ridge | Private Cabin w/ Mountain Views

Cozy Historic Cabin w/ stellar view of Big Schloss

Poplar Perch - Modern Cabin, King Bed, Fireplace
Private cabin rentals

Shenandoah Riverfront Cabin - Eagle Sightings

Trofton Solace - River View

Shadow Ridge - A cabin for 2 with a fantastic view

The Log Cabin

The Hideaway Lakeside Cabin: WiFi + Lake Access

Serenity by the Stream

Pio- New cabin! Riverfront!

Mountain Views, Game Room, Sauna, 3 Primary Suites
Destinations to explore
- Norfolk Holiday rentals
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- Washington Holiday rentals
- East River Holiday rentals
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- Apartment rentals Winchester
- Fitness-friendly rentals Winchester
- Rentals with a patio Winchester
- Rentals with breakfast Winchester
- Hotel rooms Winchester
- Rentals with a washing machine and dryer Winchester
- Rentals with a fireplace Winchester
- House rentals Winchester
- Pet-friendly rentals Winchester
- Flat rentals Winchester
- Rentals with pools Winchester
- Family-friendly rentals Winchester
- Rentals with outdoor seating Winchester
- Cottage rentals Winchester
- Cabin rentals Virginia
- Cabin rentals United States
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Cunningham Falls State Park
- Berkeley Springs State Park
- Cacapon Resort State Park
- Whitetail Resort
- South Mountain State Park
- Jiffy Lube Live
- Harpers Ferry National Historical Park
- Green Ridge State Forest
- Shenandoah River Outfitters
- Sky Meadows State Park
- Reston Town Center
- Bluemont Vineyard
- Antietam National Battlefield
- Rock Gap State Park
- Shenandoah Caverns
- Museum of the Shenandoah Valley
- Skyline Caverns
- Hollywood Casino At Charles Town Races
- Old Town Winchester Walking Mall
- Dulles Town Center
- Weinberg Center for the Arts




