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Orchard House with Wintergreen Advantage

Photo gallery for Orchard House with Wintergreen Advantage

A spacious living room with a fireplace, large windows, and a cozy seating area.
A wooden staircase with a geometric railing, a large wooden door, and a small table with a lamp.
A spacious living room with a large sectional sofa, a coffee table, and a fireplace. There is a staircase leading to an upper level, and wooden paneling on the walls.
Pool
Exterior

Reviews

10 out of 10
Exceptional
Nestled in the mountains, this 5-bedroom vacation home accommodates 10 guests with 5 bathrooms. It includes 1 hot tub and 1 indoor pool. Enjoy kayaking, fishing, hiking, and biking nearby. The property features a patio. Skiing opportunities are also accessible in the area. Wintergreen Resort and Raven's Roost Overlook are nearby attractions.

Highlights

  • Private garden
    A rare find — relax in the peaceful, private garden space.
  • Discover nearby landmarks
    Close to Wintergreen Resort
5 bedrooms5 bathroomsSleeps 10

Popular amenities

  • Indoor pool
  • Spa pool on site
  • Garage parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View map
Wintergreen, VA
  • Place, Wintergreen Resort
    ‪14 min walk‬
  • Place, Bold Rock Hard Cider Nellysford Cidery
    ‪20 min drive‬
  • Place, University of Virginia
    ‪55 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪65 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

2 Double Beds

Bedroom 3

1 King Bed

Bedroom 4

2 Single Beds

Bedroom 5

1 King Bed

5 bathrooms

Bathroom 1

Bathtub · Toilet · Jetted bathtub

Bathroom 2

Toilet · Shower only · Jetted bathtub

Bathroom 3

Toilet · Shower only · Jetted bathtub

Bathroom 4

Toilet · Shower only · Jetted bathtub

Bathroom 5

Toilet · Shower only · Jetted bathtub

Spaces

Deck or patio
Kitchen
Kitchenette
Balcony
Separate dining area
Garden
Dining area

About this property

Orchard House with Wintergreen Advantage

A Beautifully Appointed Mountain Retreat at Wintergreen
Orchard House is a distinctive five-bedroom, six-and-a-half-bath mountain home near Wintergreen’s Devils Knob area and less than a mile from the Wintergarden Spa. Thoughtfully refurnished in 2023, the home pairs beautiful antiques and collected pieces with comfortable contemporary furnishings, creating an inviting retreat that feels both sophisticated and wonderfully livable.
At the heart of the home is the dramatic great room, where soaring vaulted ceilings and a wall of windows bring the mountain setting indoors. Handsome wood bookcases, a wood-burning fireplace, and generous seating create an ideal gathering place, while an 85-inch television makes evenings by the fire just as appealing as days spent exploring Wintergreen.
The spacious, beautifully equipped kitchen was designed for cooking and gathering, with glass-front cabinetry, a dedicated coffee station, gas range, double ovens, three dishwashers, an expansive center island, and a separate prep sink. Just beyond, the dining room's impressive table seats 10—perfect for leisurely breakfasts before a day on the slopes, celebratory dinners, or long evenings spent together.
One of Orchard House's most special features is its expansive outdoor deck, accessible directly from the main living areas. Surrounded by the natural beauty of Wintergreen, the deck offers multiple seating areas, outdoor dining, and retractable awnings for comfortable days outside. It is a wonderful place for morning coffee, afternoon conversation, dinner outdoors, beautiful mountain sunsets, and quiet evenings beneath the stars.
The first-floor primary suite is a retreat of its own, with a fireplace framed by built-in bookcases, a Peloton Bike+, and the unusual convenience and privacy of two full bathrooms, each with its own dressing and closet area.
Upstairs, an open loft and charming reading room with a desk overlook the great room. Two generously sized bedrooms—one with a King bed and one with two Queen beds—each offer a private full bathroom, walk-in closet, and flat-screen television.
For guests who appreciate additional privacy, Orchard House offers two separate accommodations just steps from the main house and easily reached from the back deck. The private guest house is especially spacious, with a King sleeping area, comfortable living area, wood-burning fireplace, full kitchen, washer and dryer, large full bathroom, and its own deck. It offers the privacy of a separate residence while remaining conveniently connected to the main house.
A separate carriage-house bedroom above the two-car garage offers two Twin beds, a wet bar, private full bathroom, and gas fireplace, creating another comfortable and private space for guests.
Outside, a fenced backyard provides additional space for families to enjoy the mountain setting. A convenient laundry room off the main kitchen, easy outdoor access, and ample parking in the circular driveway make the house as practical as it is beautiful.
Whether the day is spent skiing, hiking, enjoying the resort, or simply lingering over coffee and a good book, Orchard House offers something increasingly rare in a vacation rental: the warmth, character, and thoughtful details of a beautifully furnished private home, with room for everyone to relax and enjoy being together.
Special Features
• Five bedrooms and 6.5 bathrooms
• Flexible accommodations: 3 Kings, 2 Queens, and 2 Twins
• Expansive furnished deck with outdoor dining, multiple seating areas, and retractable awnings
• Multiple fireplaces
• First-floor primary suite with two private full bathrooms and dressing areas
• Well appointed kitchen with recently upgraded appliances
• First floor private guest house with King bed, living area, wood-burning fireplace, full kitchen, full bath, washer/dryer, and private deck
• Separate carriage-house bedroom with two Twin beds, gas fireplace, wet bar, and private full bath
• Full laundry facilities
• Central air conditioning
• High-speed Wi-Fi
• Two-car garage and ample circular-driveway parking
• Non-smoking
• Just two steps to the main entrance
• Near Devils Knob and less than one mile from the Wintergarden Spa, outdoor and indoor pools and fitness facilities

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 3859122vb
Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Wintergreen

Located in Wintergreen, this holiday home is in the mountains. Wintergreen Resort and Sherando Lake Recreation Area are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Wildlife Center of Virginia and Shenandoah Valley Art Center. Kayaking, fishing and swimming offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking/biking trails nearby.
Map
Wintergreen, VA

What's nearby

  • Wintergreen Resort - 14 min walk - 1.2 km
  • Bold Rock Hard Cider Nellysford Cidery - 20 min drive - 21.1 km
  • Rockfish Gap Entrance Shenandoah - 30 min drive - 37.4 km
  • University of Virginia - 55 min drive - 76.2 km
  • John Paul Jones Arena - 59 min drive - 78.0 km

Getting around

  • Staunton Station - 41 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 61 min drive

Restaurants

  • ‪Belties - ‬19 min drive
  • ‪Devils Backbone Brewing Company - ‬14 min drive
  • ‪Margarita's The Flavor of Mexican - ‬18 min drive
  • ‪The Edge - ‬5 min drive
  • ‪Iron & Ale At Wintergreen Resort - ‬23 min drive

Frequently asked questions

Does Orchard House with Wintergreen Advantage have a pool?

Yes, this property has an indoor pool.

How much does it cost to stay at Orchard House with Wintergreen Advantage?

As of 4 Sept 2026, prices found for a 1-night stay for 2 adults at Orchard House with Wintergreen Advantage on 1 Nov 2026 start from AU$2,011, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

Is Orchard House with Wintergreen Advantage pet-friendly?

No, pets are not allowed at this property.

How much is parking at Orchard House with Wintergreen Advantage?

On-site parking is available at the property.

What time is check-in at Orchard House with Wintergreen Advantage?

Check-in begins at 4:00 PM.

What time is check-out at Orchard House with Wintergreen Advantage?

Checkout is at 11:00 AM.

Where is Orchard House with Wintergreen Advantage located?

Situated in the mountains, this holiday home is within 1 mi (2 km) of George Washington National Forest and Wintergreen Resort. Raven's Roost Overlook is 2.9 mi (4.6 km) away.

About the host

Hosted by Reservations

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Premier Host

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