House holiday rentals in Winchester

4.94 out of 5 average rating, 158 reviews

The interior of the tiny home features warm wooden walls and a skylight, providing natural light. A compact kitchenette is visible, along with a seating area that includes two metal chairs. A sliding door offers a view into the outdoor space.

Home in Harpers Ferry

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

Superhost

A well-maintained exterior showcases a brick building with a white double door entrance. Surrounding greenery includes manicured lawns and bushes, enhancing the natural setting. The entrance is easily accessible, providing a welcoming approach to the ground-level unit.

Home in Inwood

4.87 out of 5 average rating, 704 reviews

Arden House, Inwood WV

Ground level two room unit. No steps. Separate entrance from main house. Private entrance and parking. There is an entrance room with a double bed, twin bed, sofa and full refrig.. In a separate living area, there is a queen bed, TV, bathroom, desk, table, microwave, convection oven, air fryer, gas fireplace. No oven. Outside there is a large area to use outdoor gas grill, picnic table and fire pit. Dogs allowed and must be kept on a leash when outside. Please NO CATS. The owner is allergic

A cozy corner features a cushioned armchair adorned with decorative pillows, next to a small dark wood table with a lamp. A decorative bookshelf holds various books, with warm sunlight illuminating the space. A wooden staircase leads to the upper level.

4.98 out of 5 average rating, 214 reviews

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 !

4.91 out of 5 average rating, 133 reviews

A spacious outdoor area is displayed, featuring a neatly mowed lawn with several chairs arranged in a circle. The scenic backdrop includes rolling hills and mountains under a colorful sky filled with clouds, enhancing the serene atmosphere.

Home in Middletown

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 two 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

4.97 out of 5 average rating, 614 reviews

A welcoming single-story house is shown, featuring a front yard with neatly arranged shrubs and flowers. A pathway leads to the entrance, which is flanked by potted plants. A carport is visible on one side, providing covered parking.

Home in Edinburg

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.

4.97 out of 5 average rating, 118 reviews

A spacious basement area is shown, featuring a large, comfortable couch arranged around a coffee table. An exercise treadmill is positioned nearby. A ping pong table adds activity options, while windows provide natural light. The decor includes framed artwork on the walls.

Home in Bristow

Big Basement in Bristow, VA

Spacious private basement just minutes from Jiffy Lube Live, 30 miles from D.C., and an hour from Shenandoah. Nearby, enjoy movie theaters and great restaurants. The basement features a private entrance, cozy bed, couches, a private bathroom, a kitchenette with a microwave and fridge (no kitchen sink, stove, or oven), plus a game/exercise area. Whether you're unwinding after a concert, watching TV, playing games, or working out, this space offers comfort and convenience for a relaxing stay.

A spacious living area features a large sectional sofa accented with soft pillows. A stone gas fireplace is positioned beneath a wall-mounted television. Tall windows allow natural light to flood the room, offering views of the surrounding landscape. A ceiling fan and track lighting enhance the comfort and functionality.

4.94 out of 5 average rating, 208 reviews

Hot tub w/ Sunset Views! Secluded mountain chalet!

Secluded chalet near the top of a mountain on 8 acres, just 70 minutes from downtown DC, 20 minutes to old town Front Royal, close enough to get Instacart from groceries, Costco and Target, and private enough to enjoy your sunset view from the deck every night and to not see any other homes! The home is at the end of a long gravel road and parking in a small cul-de-sac. Dogs are allowed for a $75 fee per stay for the 1st, $25 after, up to 3 dogs max, extra fees charged after reservation.

A recreational space features an air hockey table in the foreground, with a dartboard and seating area visible in the background. A smart TV and indoor putting green are showcased along a wall adorned with a unique neon sign. Natural light brightens the inviting area.

4.95 out of 5 average rating, 168 reviews

Modern Getaway, Game Room, Spa, Near Shenandoah NP

Welcome to our modern retreat in the beautiful Shenandoah Valley! 🌄 With its chic design and luxurious amenities, our retreat is the perfect escape from the hustle and bustle of everyday life. Whether you're planning a romantic getaway, a girls' weekend to reconnect and explore wineries, a golf trip with the guys, or a family vacation to enjoy the great outdoors, we've got you covered. Explore nearby attractions like Shenandoah National Park, Skyline Caverns, and historic Front Royal.

The front porch features two white rocking chairs with red cushions, positioned next to a welcoming red door adorned with a wreath. Lush flowers bloom in a garden bed below, adding color to the inviting entrance.

4.97 out of 5 average rating, 273 reviews

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.

A historic home is positioned on a tree-lined street, featuring a charming façade with a welcoming entrance. Vibrant flowers adorn the balcony, and large windows allow natural light to enhance the warm exterior. Nearby trees provide a shaded area along the brick pathway.

4.92 out of 5 average rating, 169 reviews

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.

4.93 out of 5 average rating, 205 reviews

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.

Superhost

A modern two-story home is set among trees, featuring multiple balconies and large windows. A stone pathway guides guests to the entrance, with well-maintained grass and rocky landscaping surrounding the property. Scenic mountain views are visible in the background, enhancing the serene atmosphere.

4.8 out of 5 average rating, 143 reviews

Windy Knoll Adventure | River Front | Hot Tub!

Discover our Black Modern Charm Home, a private retreat atop 35 acres with sweeping mountain and Shenandoah River views. Relax in the hot tub overlooking the river, fish or kayak below, and unwind by the campfire in this peaceful woodland setting. 🌲♨️ Designed for comfort and escape, this modern retreat is perfect for unplugging, reconnecting, and enjoying nature at its finest. Book now for a true mountaintop getaway. ✨

Popular amenities for Winchester house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 146 reviews

The exterior of the mountain retreat is shown, featuring a rustic wooden structure with a metal roof. A stone pathway leads to the entrance, complemented by a lawn dotted with shrubs. Colorful chairs are positioned on the porch, providing a space for outdoor relaxation amidst the scenic views.

Home in Lost City

Mountain Retreat-Stunning View/Hot tub/Pool

5 out of 5 average rating, 110 reviews

Home in Massanutten

Top 1% ~ Fireside Ski Retreat w/ 2 King Suites

5 out of 5 average rating, 113 reviews

A circular fire pit is surrounded by six gray Adirondack chairs, set on gravel. Beyond, a spacious wooden deck is visible, featuring a covered area and a picnic table. The yard is fenced with trees providing a natural backdrop.

Home in Hedgesville

Spacious Retreat for Groups, Well Stocked

4.97 out of 5 average rating, 209 reviews

The exterior of the farmhouse is showcased at dusk, highlighting the blend of historic and modern architecture. A stone path leads to the welcoming entry, framed by glowing flower pots. The wraparound porch features multiple illuminated windows, reflecting a cozy and inviting ambiance.

Home in Harpers Ferry

Historic Farmhouse w/ Heated Pool, Harpers Ferry

4.93 out of 5 average rating, 122 reviews

A spacious pool area features a heated in-ground pool and spa surrounded by lounge chairs. A well-maintained lawn and shaded seating areas complement the outdoor space, while a house is visible in the background, nestled among the trees.

Home in Marshall

Clean 5BR w Heated Pool, Spa - Horse, Wine Country

4.76 out of 5 average rating, 291 reviews

An aerial view showcases the nine-acre estate featuring a charming stone house, surrounded by vibrant fall foliage. The swimming pool is visible adjacent to a patio area, with a gazebo nearby. The spacious driveway accommodates several vehicles, enhancing accessibility.

Home in Strasburg

Cedar Creek Wayside Castle

5 out of 5 average rating, 100 reviews

A spacious solarium features large windows allowing plenty of natural light to fill the room, with views of the surrounding greenery. A comfortable seating area is arranged with a mix of sofas and chairs, complemented by various plants adding a touch of nature. The heated concrete floor enhances comfort in this inviting gathering space.

Home in Knoxville

An Escape Bordering National Park land 1 mi to C&O

4.91 out of 5 average rating, 153 reviews

An inviting outdoor space is presented, featuring a wooden deck with several Adirondack chairs. A hot tub is positioned at one end, surrounded by lush greenery. The farmhouse is visible in the background, showcasing a screen porch and a tree-lined yard.

Home in Quicksburg

Overbank Riverfront Estate~Hot Tub~Pool~Views

Weekly house rentals

4.93 out of 5 average rating, 170 reviews

A spacious screened porch features a comfortable sectional sofa arranged around a wooden coffee table. Natural light filters through the screens, providing views of the surrounding trees and expansive yard.

Home in Luray

Cabin on River with Private Waterfront, Fast Wifi

4.96 out of 5 average rating, 246 reviews

A charming cabin is positioned on a stone patio, framed by trees. The early morning sun casts warm light over the scene, enhancing the natural landscape. A fire pit is visible in the foreground, surrounded by a low stone wall, creating an inviting outdoor gathering space.

Home in Chester Gap

The Nest

4.96 out of 5 average rating, 71 reviews

A well-lit deck hosts a modern soaking tub, surrounded by forest views. Steps lead down from the deck, which is adorned with warm lighting that highlights the natural wood. The evening sky offers soft hues as the sun sets beyond the trees.

Home in Harpers Ferry

Gorgeous cabin on Blue Ridge

4.97 out of 5 average rating, 350 reviews

A charming cabin is observed surrounded by a natural landscape, featuring large windows that invite ample daylight. Stone steps lead to the entrance, framed by landscaped greenery. Adjoining seating provides a comfortable area to enjoy the serene setting.

Home in Paris

Ashby's Perch -- A Very Special Retreat

A private outdoor patio area features a fire pit surrounded by four seating chairs and a shaded table under an umbrella. A green lawn is complemented by a fenced perimeter and flower pots, creating a relaxed environment for outdoor gatherings.

4.95 out of 5 average rating, 128 reviews

Shenandoah Getaway | Cozy, Clean & Well-Located

4.92 out of 5 average rating, 258 reviews

A panoramic view of the snowy landscape stretches across the horizon, with undulating hills and valleys visible beneath a clear blue sky. Trees, dusted with snow, create a serene foreground, enhancing the sense of tranquility and nature.

Home in Linden

Valley Vista, stunning views in wine country

4.95 out of 5 average rating, 122 reviews

An open living space features a modern fireplace in the center, surrounded by comfortable seating on a plush area rug. Large windows offer expansive views of the outdoors, while a dining area is visible in the background, illuminated by natural light.

Home in Basye

Unique home with mountain views at Bryce Resort!

Home in Blue Ridge Summit

The exterior of a colonial era spring house showcases a natural stone base supporting a wooden structure. A spacious balcony with wooden railings extends from the second floor. Brightly colored hanging flower pots add a touch of greenery to the inviting façade.

4.99 out of 5 average rating, 614 reviews

Colonial Era Spring House

Private house rentals

Home in Round Hill Village

The exterior of a two-story farmhouse is presented, featuring a white façade and a welcoming front porch. A classic brick chimney adds character, while a well-maintained lawn and brick pathway lead to the entrance. Surrounding trees create a serene atmosphere, enhancing the property’s natural charm.

4.97 out of 5 average rating, 72 reviews

Historic Farmhouse, Fully Renovated in Fall 2023

5 out of 5 average rating, 19 reviews

Home in Clear Brook

Cedar Hill Cottage- 3 mi to I-81 & Rt 11

4.93 out of 5 average rating, 99 reviews

The A-frame lodge features a distinctive shape with a steeply pitched roof and large front windows. A welcoming green door is framed by wooden steps, leading to a spacious deck. Surrounding greenery offers a peaceful, natural setting.

Home in Berkeley Springs

Berkeley Springs Jungle Lodge

5 out of 5 average rating, 26 reviews

Home in Luray

Millstone Cottage | EV Charger, King Bed, Luxury

4.96 out of 5 average rating, 24 reviews

Home in Lovettsville

The Dutchmans Creek Farmhouse

4.88 out of 5 average rating, 16 reviews

A charming exterior showcases a brick and wood house beneath a red awning. Lush green shrubs and manicured lawns frame the entrance, with a brick pathway leading toward the front door. Tall trees provide a natural backdrop, enhancing the serene atmosphere.

Home in Martinsburg

The Boston - Family Escape

A single-story country home is situated amidst a spacious lawn, bordered by mature trees. The exterior features a combination of brick and siding, with a welcoming entrance. The property exudes a tranquil ambiance, surrounded by the greenery of the landscape.

4.96 out of 5 average rating, 78 reviews

Misty Meadow has quite setting in the country.

A two-story house is shown with a covered porch supported by wooden columns. The white exterior contrasts with the lush green lawn and trees nearby. Pathway lights line the walkway leading to the entrance, while the evening sky adds a subtle hue to the scene.