
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.

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 !

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.

COZY River Cabin, HOT TUB, Privacy, Romance, Fun!
Enjoy a River Front Colorful Fall or Cozy Winter Weekend in your HOT TUB at Skyhouse! Fully-remodeled with million dollar views overlooking the river, steps to the water's edge and floating dock! Relaxation, romance, outdoor adventure or just peace and quiet watching the leaves or snow fall inside on your shearling covered comfy couch with views overlooking the river! Ideal for vacay, workcay, mini-moon, or special occcation. 1 hr from NoVA/DC off I-66, 10 mins to town of Front Royal!

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 🐾.

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 - 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.

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.
Popular amenities for cabin rentals in Winchester
Cabin rentals with a hot tub

Vintage Riverfront Log Cabin “Emma” w/hot tub

Charming, cozy cabin on the ridge.

Wild, Wonderful Five-Bedrm Loghome

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

Secluded Cabin | Hot tub | Kayaks | 2 min to Lake

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

Mtn. Retreat, Hot Tub, Firepit, Stargazing, SNP!

Hobbit House in the Shenandoah Virginia "Shire"
Pet-friendly cabin rentals

The River House

VIEWS! Fire Pit|River Access|Pool Table|Arcade

Design-forward cabin in the woods

Venture Cabin in Shenandoah Valley

Island cabin

Cozy Historic Cabin w/ stellar view of Big Schloss

Double Spur Outfitters' Brook Cabin

Overlook Cabin - Hot Tub, Amazing Views, Fireplace
Private cabin rentals

Trofton Solace - River View

Bear Pines Retreat ~ Game Room ~ Screened Porch

The Vale at Será - Modern Retreat w/Sauna

New! Zen Cabin in the Clouds

Sleepy Hollow Log Cabin

Serenity by the Stream

Long Meadow Cabin Near Wineries & Hiking

Mountain View, Beautiful Sunsets- Tanglewood Cabin
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- East River Holiday rentals
- Washington Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Pocono Mountains Holiday rentals
- Outer Banks Holiday rentals
- Rentals with a washing machine and dryer Winchester
- Fitness-friendly rentals Winchester
- Family-friendly rentals Winchester
- Cottage rentals Winchester
- House rentals Winchester
- Rentals with a fireplace Winchester
- Apartment rentals Winchester
- Hotel rooms Winchester
- Rentals with a patio Winchester
- Rentals with outdoor seating Winchester
- Flat rentals Winchester
- Rentals with pools Winchester
- Pet-friendly rentals Winchester
- Rentals with breakfast Winchester
- Cabin rentals Virginia
- Cabin rentals United States
- Whitetail Resort
- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Cunningham Falls State Park
- Berkeley Springs State Park
- Gambrill State Park
- Cacapon Resort State Park
- South Mountain State Park
- Jiffy Lube Live
- Sky Meadows State Park
- Shenandoah River Outfitters
- Harpers Ferry National Historical Park
- Green Ridge State Forest
- Big Cork Vineyards
- Cooter's Place
- Rock Gap State Park
- Bluemont Vineyard
- Antietam National Battlefield
- Reston Town Center
- Skyline Caverns
- Old Town Winchester Walking Mall
- Museum of the Shenandoah Valley
- Shenandoah Caverns




