
Cabin holiday rentals in Winchester
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Top-rated cabin rentals in Winchester
Guests agree: these cabins are highly rated for location, cleanliness and more.

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.

The Nest: Cozy Chalet - Wi-Fi, Deck and Grill
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 !

Shenandoah Escape ~Sauna ~Walk to SRO ~King Bed
Escape to the beauty of the Shenandoah Mountains and enjoy easy access to the Shenandoah River Outfitters from this custom log cabin in Luray. Relax in the sauna, unwind in the hanging basket chair on the deck, play corn hole in the yard, swing on the under deck swings, or lounge around the fire pit. Spend time kayaking, tubing, or rafting down the Shenandoah River... we are the closest Airbnb to the Shenandoah River Outfitters! The scenery and memories you will make are spectacular!

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!

A-Frame Cabin Escape in GW Natl Forest Lost River
Nestled in the wooded hillsides of the George Washington National Forest just outside Wardensville in the Lost River area, Santi's Lost Stream provides a serene retreat from the stresses of urban life and is the perfect base to enjoy all the area has to offer from hiking to cycling, and more. And blazing-fast fiber internet to help you stay connected. Booked for your dates? Check out our cousin cabin High View Hideaway just a few miles away (Property# 39899541).

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.

Hidden in Shenandoah Valley|Pool|Pets|Fire Pit
Hidden in the Valley sits on 30 private, wooded acres adjoining the George Washington National Forest. This remote property offers a pool, fire pit and foot trails throughout, perfect for your furry companions! If you’re looking for a true escape to nature, surrounded by Virginia’s best hiking trails, wildlife and clear, starry night skies, Hidden in the Valley is the getaway for you!

The Log Cabin
A restored 1700's log cabin in a convenient location to Shepherdstown and surrounding attractions. One bedroom upstairs with a queen sized bed. One pull out sofa in the downstairs living area. In the summer of 2018, we have added an intimate brick patio area suitable for alfresco dining and for fireside sitting. It is peaceful. It is beautiful. You will not want to leave.
Popular amenities for cabin rentals in Winchester
Cabin rentals with a hot tub

Lake view! Hot tub! Fire pit! Arcade Game King Bed

Vintage Riverfront Log Cabin “Emma” w/hot tub

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

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

Hideaway Cabin- Tiny Cabin, Hot Tub, View, Firepit

Timber Creek: Falls - A Shenandoah Cabin

The Chapter House: Hot Tub + Mountain Views

Lost River Nordic House, dog friendly + hot tub
Pet-friendly cabin rentals

Design-forward cabin in the woods

Modern Eclectic Treetop Cabin With Hottub

Wilderness Ridge | Private Cabin w/ Mountain Views

Waterfront Cabin on the Potomac River w/ Hot tub

Poplar Perch - Modern Cabin, King Bed, Fireplace

Modern Wooded Retreat, Fire Pit & Deck

The Sanctuary

Shenandoah Log Cabin on beautiful farm
Private cabin rentals

Private Hot Tub & Sauna | Cozy Cabin Near SNP

Kona's Cabin — King Bed, Fireplace, Pet Friendly

The Philosopher’s Retreat

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

The 1744 Custom Cabin

Rocky Ridge

The Hideaway Lakeside Cabin: WiFi + Lake Access

Rivah Retreat, HotTub~Firepit-Fishing-Deck-Private
Destinations to explore
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- Cottage rentals Winchester
- Rentals with a washing machine and dryer Winchester
- Rentals with a patio Winchester
- Rentals with outdoor seating Winchester
- Rentals with a fireplace Winchester
- Hotel rooms Winchester
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- Rentals with pools Winchester
- Pet-friendly rentals Winchester
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- Cabin rentals Virginia
- Cabin rentals United States
- Luray Caverns
- Stone Tower Winery
- Whitetail Resort
- Cunningham Falls State Park
- Shenandoah Valley Golf Club
- Bryce Resort
- Berkeley Springs State Park
- Gambrill State Park
- Cacapon Resort State Park
- Creighton Farms
- Robert Trent Jones Golf Club
- South Mountain State Park
- River Creek Club
- Notaviva Vineyards
- Sly Fox Golf Club
- Twin Lakes Golf Course
- Bowling Green Country Club
- Reston National Golf Course
- Dinosaur Land
- JayDee's Family Fun Center
- Herndon Centennial Golf Course
- Warden Lake
- The Golf Club at Lansdowne
- Big Cork Vineyards




