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The Wintergreen Chalet

Photo gallery for The Wintergreen Chalet

A wooden cabin with a snow-covered roof, a visible staircase, and a sign indicating '58 South Forest Dr.'
A kitchen with wooden cabinets, a granite countertop, a refrigerator, a sink, and a window with a view of trees.
A hot tub on a wooden deck with a wooden railing and a white fence in the background.
A stone fireplace with a deer head, a wooden ceiling, and a stone wall.
A hallway with a vanity, wooden chair, and framed pictures on the walls.

Reviews

9.2 out of 10
Wonderful

Highlights

  • Arcade/game room
    A rare find - fun for all ages with on-site arcade/game room.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Wintergreen Resort
Sleeps 14•6 bedrooms•9 beds

Popular amenities

  • Shared communal pool
  • Hot tub on site
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning

Explore the area

View in a map
Roseland, VA
  • Place, Wintergreen Resort
    ‪6 min walk‬
  • Place, Bold Rock Hard Cider Nellysford Cidery
    ‪21 min drive‬
  • Place, University of Virginia
    ‪56 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪66 min drive‬

Rooms & beds

6 bedrooms (sleeps 14)

2nd floor

2 Single Beds

2nd floor

1 Queen Bed

Lower level

2 Queen Beds

Lower level

1 Queen Bed

Lower lever

2 Single Beds

Main floor Master

1 King Bed

4 bathrooms, 1 half bathroom

Bathroom 1

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Spaces

Deck or patio
Kitchen
Garden

About this property

The Wintergreen Chalet

The Wintergreen Chalet is a sprawling 6-bedroom 4.5 bath home located at the top of Devil's Knob Mountain within the Wintergreen Resort in the Blue Ridge Mountains of Virginia. The home sleeps 12-14 comfortably and is available for rent daily, weekly or monthly.

Our home is set on a private road at one of the highest elevation points in the resort and offers beautiful seasonal views of the Shenandoah Valley. It is within 1 mile of most amenities including golf, tennis, snow skiing, swimming, hiking, restaurants and the Winter Garden Spa. The large wooded lot provides plenty of privacy and a great place for little explorers to climb the natural rock formations surrounding the property.

In addition to the professionally decorated 4,000 square-foot interior the home has over 1,000 square feet of outdoor deck space. A 6-person hot tub is also provided for year-round fun.
Our prices include all fees. No hidden fees.

Add dates for prices

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House Rules

Check in after 4:00 PM
Minimum age to rent: 23
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 allowed: in designated areas

Important information

You need to know

Property Registration Number 1503
Property # 2370886vb
This property is managed by a private host (a party not acting within their trade, business or profession). EU consumer law, including the right of withdrawal, will not apply to your booking. The cancellation policy set by the private host will cover your booking.
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 indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
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. Fishing offers a great chance to get out on the surrounding water, or you can seek out an adventure with mountain biking, mountain climbing and hiking/biking trails nearby.
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Map
Roseland, VA

What's nearby

  • Wintergreen Resort - 6 min walk - 0.6 km
  • Bold Rock Hard Cider Nellysford Cidery - 21 min drive - 21.8 km
  • Rockfish Gap Entrance Shenandoah - 31 min drive - 38.1 km
  • University of Virginia - 56 min drive - 76.9 km
  • John Paul Jones Arena - 60 min drive - 78.6 km

Getting around

  • Staunton Station - 43 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 58 min drive

Restaurants

  • ‪Belties - ‬20 min drive
  • ‪Hill Top Berry Farm & Winery - ‬23 min drive
  • ‪Devils Backbone Brewing Company - ‬15 min drive
  • ‪The Edge - ‬6 min drive
  • ‪The CopperMine - ‬6 min drive

Frequently asked questions

Is The Wintergreen Chalet pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at The Wintergreen Chalet?

As of 21 Aug 2026, prices found for a 1-night stay for 2 adults at The Wintergreen Chalet on 19 Oct 2026 start from £866, 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.

How much is parking at The Wintergreen Chalet?

On-site parking is available at the property.

What time is check-in at The Wintergreen Chalet?

Check-in begins at 4:00 PM.

What time is check-out at The Wintergreen Chalet?

Checkout is at 11:00 AM.

Where is The Wintergreen Chalet located?

This family-friendly Wintergreen holiday home is located in the mountains, within a 5-minute walk of George Washington National Forest and Wintergreen Resort. Reids Gap Trailhead and Raven's Roost Overlook are also within 9 miles (15 km).

About the host

Hosted by Martha Walker

Host profile image
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