
Holiday rentals with a fireplace in Winchester
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Top-rated Accommodation with Fireplace in Winchester
Guests agree: these holiday homes with a fireplace are highly rated for location, cleanliness and more.

COZY+SEXY Private Country Escape! HOT TUB & Views~
Look no further for privacy, intimacy, & fun~ Foxy is your perfect escape, located in the Shenandoah Valley & surrounded by a 1000 private acres but only 10 minutes from downtown Winchester. Offering a uniquely glamorous experience, surrounded by all the beauty of nature. Indulge in luxury & tranquility with amenities including your own private patio with hot tub and million dollar views of the Blue Ridge Mountains. Inside, a full chef's kitchen leading to a sexy, opulent master bedroom suite...

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 Sanctuary in the Shenandoah Valley
Rest and unwind with your family or friends at the Sanctuary. We designed this space with gathering and connection in mind. Enjoy natural lighting and open concept living in our newly renovated 19th century church building. Meals can be prepared in the spacious kitchen and enjoyed together around a 12-foot farmhouse table. After meals transition to our spacious yet cozy living room. If you don't want to stay in, explore the Shenandoah Valley's great outdoors, rich history, and fine dining.

Luxury Mountain Getaway: Sunsets, Wines & Views
Celebrate your special moment in chic elegance and 5-star amenities for adult couples only. You deserve the Sunset Rouge. It's a destination in a relaxed and romantic setting to escape anxiety of kids, city, and work. Let the fun décor and panoramic views inspire the writer and artist within. During the day, take flight with eagles at eye level. At night, gaze into the heavens to catch a falling star. Within 2 miles is Lake Shannondale with beach access provided by the Mountain Lake Club.

Scarborough Fair walk to downtown two story apt
Come to downtown Winchester get the true feel of the city. Park & Walk to beautiful Handley Library, take a stroll to the much loved walking mall to the many shops & restaurants. Scarborough Fair is the place to enjoy the time w/family and friends. Three bedrooms, two levels, three porches, fenced yard. Eclectic & comfortable you will love your stay in this wonderful spot downtown. Looking for more space? or have any additional questions? Reach out on social media: Michele Bouve Hoffman.

John Pope Cabin Browntown Va. We now have Starlink
Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. An inviting front porch with swing is waiting for you @walnuthillcabin

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 !

Historic District Charm On Cameron Street
Charming home located in the historic district of Winchester. A short walk to the walking mall,restaurants, shopping, farmer's markets,breweries and more. Convenient to Shenandoah University, Winchester Medical Center, many museums including the Museum of the Shenandoah Valley, George Washington Hotel, Skyline Drive, 81 and more. Big deck and a half court basketball in the back yard. We have added a work/office area with a desk and chair ideal for working or schooling from home.

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

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.

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.

The Far View Retreat | Hot Tub + Scenic Views
Discover "The Far View Retreat", a private cabin getaway designed for rest and reconnection. Once one of the area’s original hunting cabins, it’s been thoughtfully reimagined with warmth and care. Here, panoramic views stretch for miles, mornings unfold quietly on the screened-in porch, and evenings fade into the glow of twilight and a sky full of stars.
Popular amenities for Winchester Accommodation with Fireplace
Holiday House Rentals with a fireplace

The Burrow ~ Our guest reviews say it all!

The Nest

Shenandoah Siesta

Arden House, Inwood WV

Sunset Haven- Skyline Drive/Hot Tub/Game Room/Pets

Our Shangri La

The Country French Cottage at High Meadows Estate

Shenandoah Mountains- North Mountain Manor
Apartment rentals with a fireplace

The Boundary House Apartment

Massanutten Cozy Condo-Hot Tub&Jacuzzi, EV Charger

Downtown Suite with Outdoor Terrace

Relax and restore at Mockingbird spa and retreat

Dog-Friendly Downtown Studio — Walk to Park&Shops

Pet-Friendly Shenandoah Mountain Retreat

Stonewall Abbey Apartment

Charming 1 Bedroom Apt- Best Location in Downtown
Villas with a fireplace

The Mulberry Manor House

Hot Tub, Game Room, Pizza Oven, Fire Pit, Pets

Hamatreya- Panoramic Shenandoah Views

Chateau Solace: Lux Spa Retreat w/ Hot Tub & Views

Dream House on Potomac Canyon South Rim

Wilderness Presidential Resort in Virginia

Spacious and Beautiful Home with "Hygge"!

Huge Private Wooded Estate 5BR/3BA in Manassas, VA
Quick stats about holiday rentals with a fireplace in Winchester

Total holiday rentals
Explore 30 holiday rentals in Winchester

Nightly prices starting at
Winchester holiday rentals start at $56 AUD per night before taxes and fees

Verified guest reviews
Over 1,090 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
20 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
30 of Winchester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Winchester rentals

4.8 Average rating
Winchester stays are highly rated by guests—averaging 4.8 out of 5!
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- Rentals with a fireplace Virginia
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- Luray Caverns
- Stone Tower Winery
- Bryce Resort
- Berkeley Springs State Park
- Cunningham Falls State Park
- Harpers Ferry National Historical Park
- Jiffy Lube Live
- South Mountain State Park
- Cacapon Resort State Park
- Shenandoah River Outfitters
- Whitetail Resort
- Hollywood Casino At Charles Town Races
- Green Ridge State Forest
- Reston Town Center
- Rock Gap State Park
- Sky Meadows State Park
- Antietam National Battlefield
- Weinberg Center for the Arts
- Skyline Caverns
- Dulles Town Center
- Bluemont Vineyard
- Shenandoah Caverns
- Old Town Winchester Walking Mall
- Museum of the Shenandoah Valley





