
House holiday rentals in Winchester
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Top-rated house rentals in Winchester
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Spectacular View, PET FREE, Skylight and Hot Tub
Enjoy majestic views of the Shenandoah River in our tiny home centrally located just 5 mins from AppalachianTrail, 6 mins from the rivers, 12 mins from Old Town Harpers Ferry, quiet peace no train noise unlike old town. Large patio, courtyard, firepit, hammock, "Mind Blowing" 2 person soaking tub. The outdoor space provides private vistas of Shenandoah, moonlit nights, star gazing, or taking in beautiful scenery while enjoying a relaxing shower in our cedar outdoor shower under the sun or stars

Cozy Reliance Retreat with Beautiful Views
Welcome to the Reliance Retreat in the heart of the Shenandoah Valley! Our luxurious space is inviting and tranquil. Whether you're just passing through or need some peace and quiet away from the city, this cozy house has an amazing mountain view we know you'll enjoy. The house sleeps four and includes all the amenities you'll need in every area of the home. We hope you'll grab a book, your favorite snacks and find yourself a cozy spot whether it's inside, on the patio, or out by the fire pit

Lindas Country Cottage
Come and relax in our Little County Charmer If needed for extended t. Under 2 miles from Interstate. 15 min from Charlestown Casino and horse racing. JD’s Fun Center with pool for children. ..2 hrs from Massanuttan . Take a ride to Historic Berkley Springs Or Harpers ferry.. Home is in a quite neighborhood. Tv Wi-Fi. Home is close to dining and fast foods delivery. So if you wanna feel right at home while visiting or town stop by and pay a visit at our small home with a little country charm

Mtn. View~Cave Hot Tub~50 Ac~ATV Trails~Fishing
Mountain home: like in the movies, on 50 acres. Includes soaring mountain views, swimming holes, hiking trails, ATV trails, fishing creek, mini white sand beach, hot tub in a cave, huge boulder rustic fire pits, cave, lake, cabanas, all in a heavy forest exclusively for guests. Private: you cannot see another house from the front porch or back decks and it has thick woods all around. At the top of the property are soaring views with 3 miles of visibility. No need to go to the national park.

Cameron Charmer pristine w/double master suites
Take a step into pure luxury in this newly renovated 1930's charmer in up and coming downtown area of Winchester. Owners have spared no expense to make this the kind of place where guests can come & forget about the rest of the world ! Incredible top of the line centralized dine in kitchen, wide open & inviting living areas, two master suites each with walk in closets & baths up lovely custom pine staircase. Come spoil yourself a bit at the Cameron Charmer, you are sure to enjoy your stay !

Jay Birds Nest - Pet Friendly
Welcome to Jay Birds nest, located in the historic town of Edinburg, Virginia. Just 1.5 miles from I-81. Fully equipped with all the comforts of home and gorgeous mountain views. Enjoy having the entire house to yourself with sleeping for 6 with 2 queen bedrooms and 1 full bedroom and one full bath. Plenty of parking with room for two cars, one under a car port. Have your morning coffee in the relaxing sunroom or in the outdoor seating area. Just a quick walk away from the Shenandoah River.

City Charmer minutes from Old Town
Renovated 1950's cottage style home. Enjoy a small house with a great front porch and large backyard with patio. Just minutes to drive and about 10-15 minutes to walk to Historic Old Town Winchester which includes numerous restaurants, bars, shopping, and often some kind of event like the Shenandoah Apple Blossom Festival! Our house is located about 65 miles West of Washington D.C. if you're looking for a day trip to the big city or just sit back and relax right here in our small town.

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.

Indigo Blue modern open vibe on tree lined street
Come stay in this lovely spacious downtown home located on a beautiful tree lined street. Enjoy its open mid century modern style & relaxing outdoor area! This 3BR 2BA home w/sunroom w/ gas fireplace & rear fully fenced courtyard perfect place to get away to & explore downtown Winchester. Walking distance to everything. Walking Mall/ Shopping /Live Music /Art/ John Handley Library/Discovery Museum. Need shorter stay? Contact info for : Michele Bouve Hoffman via google.

The Cozy Cottage-2 mins to I-81
Kick back and relax in this calm, stylish cottage. Welcome to "The Cozy Cottage". Escape the mundane and embark on outdoor adventures like fishing, hiking, rock climbing, zip-lining, history, wineries, breweries, antiquing and more from this vacation Cozy Cottage just 2 miles from I-81. We are located in Edinburg, Virginia. This 2-bedroom, 1-bathroom house offers all the modern amenities of home in a cottage-inspired living space.

Little Red Schoolhouse in Cross Junction
Step into our charming red schoolhouse—your cozy, vintage-inspired 1BR retreat! Enjoy a unique stay with modern comforts, nostalgic décor, and sun-filled spaces. Perfect for romantic getaways or peaceful escapes. High ceilings, natural light, and warm wood floors set the scene. Just minutes from scenic hikes, wineries, and local attractions. Book your unforgettable Airbnb experience now in this one-of-a-kind historic stay!

Colonial Era Spring House
A unique and private mountain top colonial era spring house, with two springs flowing thru the basement. Originally the site of a tannery in the 1700s. Here you can relax, recharge, and rejuvenate. We celebrate all four seasons where you can enjoy Mother Nature's ever changing scenery at 1300' above sea level with fresh mountain air. Our area offers many things to do, or you may choose to stay in and do nothing at all.
Popular amenities for Winchester house rentals
House rentals with a pool

Peacefield - Blue Ridge views near Culpeper

Mountain Retreat-Stunning View/Hot tub

Spacious & Charming! Large deck+Game shed+Firepit

Historic Farmhouse w/ Heated Pool, Harpers Ferry

Clean 5BR w Heated Pool/Spa - Horse & Wine Country

Cedar Creek Wayside Castle

Sunset Retreat a cabin off the beaten path

Stunning Riverfront Home w/ Pool, Hot Tub & Kayaks
Weekly house rentals

The Dutchmans Creek Farmhouse

Gorgeous cabin on Blue Ridge

Chef’s Kitchen+BBQ Patio8Min to Old TownWinchester

Misty Meadow has quite setting in the country.

So cozy

Skyview Farmhouse

Deer Chase

Compassion, Mountain View Cabin
Private house rentals

1900 Newton School-house

Purple Iris 3b 2b private oasis nr river/mountain

Winchester farm

Rivers Edge: On the River, Breathtaking views!

Mountain View Bungalow

The Reserve

Cottage on the Shenandoah

Iconic Chalet: Sauna • Hot Tub • Fire Pit • Plunge
Quick stats about house rentals in Winchester
Total rentals
30 properties
Nightly prices starting at
$31 AUD before taxes and fees
Total number of reviews
1.8K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Destinations to explore
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- Rentals with a washing machine and dryer Winchester
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- Rentals with breakfast Winchester
- Pet-friendly rentals Winchester
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- Rentals with a fireplace Winchester
- Rentals with a patio Winchester
- Hotel rentals Winchester
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- Rentals with pools Winchester
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- House rentals Virginia
- House rentals United States
- Luray Caverns
- Stone Tower Winery
- Cunningham Falls State Park
- Cacapon Resort State Park
- Shenandoah Valley Golf Club
- Gambrill State Park
- Whitetail Resort
- Berkeley Springs State Park
- Bryce Resort
- Robert Trent Jones Golf Club
- Creighton Farms
- South Mountain State Park
- River Creek Club
- Sly Fox Golf Club
- Notaviva Vineyards
- Bowling Green Country Club
- Car and Carriage Caravan Museum
- Dinosaur Land
- Twin Lakes Golf Course
- Reston National Golf Course
- JayDee's Family Fun Center
- The Golf Club at Lansdowne
- Warden Lake
- Herndon Centennial Golf Course