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The Wintergreen Chalet

Photo gallery for The Wintergreen Chalet

Exterior
Exterior
Exterior
Room
Dining

Reviews

9.6 out of 10
Exceptional
6 bedrooms4+ bathroomsSleeps 14

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning

Explore the area

View in a map
Roseland, VA
  • Place, Wintergreen Resort
    ‪5 min walk‬
  • Place, Bold Rock Hard Cider Nellysford Cidery
    ‪13 min drive‬
  • Place, University of Virginia
    ‪37 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪49 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.

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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

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
Property Registration Number 1503

We should mention

This property does not have any lifts

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 War Fields. Make sure you get close to the area's animals with activities such as game walks and birdwatching.
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Map
Roseland, VA

What's nearby

  • Wintergreen Resort - 5 min walk - 0.4 km
  • Bold Rock Hard Cider Nellysford Cidery - 13 min drive - 16.7 km
  • University of Virginia - 37 min drive - 60.8 km
  • Downtown Mall - 41 min drive - 66.3 km
  • Monticello - 43 min drive - 69.1 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
  • ‪Iron & Ale At Wintergreen Resort - ‬24 min drive
  • ‪Devils Backbone Brewing Company - ‬16 min drive
  • ‪The Market - ‬5 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 1 Apr, 2026, prices found for a 1-night stay for 2 adults at The Wintergreen Chalet on 6 Apr, 2026 start from S$528, 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 1 mi (2 km) of George Washington National Forest and Wintergreen Resort. Reids Gap Trailhead and Raven's Roost Overlook are also within 9 miles (15 km).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 20 out of 27 reviews
Rating 8 - Good. 6 out of 27 reviews
Rating 6 - Okay. 1 out of 27 reviews
Rating 4 - Poor. 0 out of 27 reviews
Rating 2 - Terrible. 0 out of 27 reviews

9.4/10

Cleanliness

9.4/10

Check-in

9.6/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

robert b.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Home was perfect for our big group. Very clean!
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Hillary K.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House suited our needs perfectly
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Gary R.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Outstanding place for a large group.
Stayed 3 nights in Oct 2025
Verified

8/10 Good

david d.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Nice house. Host was very responsive
Stayed 2 nights in Jan 2026
Verified

10/10 Excellent

Billy S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was great. House was just what we wanted
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Brian D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home made for a great ski weekend after Christmas. It was clean, with plenty of room for everybody. I definitely would rent it again if the need arises.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Nicole D.

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was great! Lots of space for six moms getting away for the weekend.
Stayed 2 nights in Oct 2025
Verified

8/10 Good

Bin W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
the host is welcome. but the facility does not maintain well. When we get there, the first problem is water leaking in kitchen. After two hours they fixed it. And then, power outage and fire alarm battery. They fixed quickly.
Stayed 3 nights in Dec 2025
Response from VrboOwner on 9 Jan, 2026
There were a few unfortunate mishaps. The leak was crazy! Guests checked out that morning with no leak. Thankful to WPOA for fixing it as quickly as possible! These guests had many more people in the house than their reservation stated.
Verified

10/10 Excellent

Scott L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place!

We had a group of six guys for a getaway weekend. Great place, would definitely stay here again. Enjoyed the open kitchen / living area and natural light.
Stayed 3 nights in Oct 2024
Verified

10/10 Excellent

Katherine W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Christmas and New Years Holiday

Very spacious. Lots of room and close to the resort!
Stayed 5 nights in Dec 2024
Verified

10/10 Excellent

William W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wintergreen Chalet

We had a great Thanksgiving weekend in the Wintergreen Chalet.
Stayed 3 nights in Nov 2021
Verified

10/10 Excellent

Thomas M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great spot for a family get together!

The whole family needed a central spot to get together for Christmas and we found this spot in Wintergreen that was perfect for our needs. The house was big enough for everyone, had a large kitchen and dining room, and was plenty of space for us to relax and enjoy the holidays. It's a bit dated in some rooms but the price and location were just right for us. Would absolutely recommend and stay there again!
Stayed 4 nights in Dec 2024
Verified

10/10 Excellent

Jennifer S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fun times with friends

Close to slopes and big enough for everyone to have their own space.
Stayed 4 nights in Jan 2025
Verified

10/10 Excellent

Renee S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful house in a great location

The pictures do not do this house justice. Kitchen was modern and had everything we needed. Beds were comfortable. Lots of space for everyone.
Stayed 2 nights in Jan 2025
Verified

10/10 Excellent

Jessica D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Second stay here and loved it again

Stayed just after new years with our children and another family. House has plenty of space for everyone and very well laid out. Not too far from slopes, short driving distance. Kids and adults both loved the hot tub after skiing all day. Thanks!
Stayed 4 nights in Jan 2025
Verified

8/10 Good

James D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Large Family Group

Family (including 19, 18 year old children) ranging down to the youngest of 15. Plenty of room and the dining room table is perfect for large groups. Eight total with other family staying in the area and coming over for dinner and game nights.
Stayed 5 nights in Jun 2023
Verified

10/10 Excellent

Erin D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Terrific large house

This house is larger than I expected, two full living areas, lots of decks, large kitchen. The location is perfect in the Wintergreen resort, a short drive from skiing for our group. We appreciated the mudroom area for wet boots, etc. It is an older home but has some updates. The heating was uneven, some bedrooms very warm, others chilly despite baseboard heaters, but we all had a terrific time and slept well. The checkers/chess board was a hit and we loved the hot tub at the end of a cold day on the slopes.
Stayed 3 nights in Feb 2024
Verified

6/10 Okay

Verified traveller

Liked: Check-in, location
Disliked: Cleanliness

Chalet Sorely in Need of Maintenance

The Chalet is an older property that hasn't been maintained adequately. While common areas are large and inviting, there are limitations including dirty kitchen equipment, scratched nonstick frying pans and cutting boards, expired filter on refrigerator water supply, dirty decks and outdoor furniture, 2 exits to the outside that are marked "Do not use," due to unsafe exterior stairs and walkways, large black ants on two floors, an inoperable shower, and noise from some animal life in an exterior bedroom wall at night. Considering the condition of the property, we felt we were overcharged. I have sent the owner an extensive list of items needing attention. Before renting this property, you would do well to be assured maintenance has been done.
Stayed 5 nights in Jul 2023
Response from VrboOwner on 24 Aug, 2023
These guests were extremely high maintenance. They called and texted every day multiple times. Our Homewatch company blew off all deck and cleaned the outdoor furniture before arrival. This home is in the woods on a mountain so debris on outside decks is unavoidable. The cookware in question has been replaced. We have never received a bad review and are working to make improvements throughout the home. 😊
Verified

8/10 Good

david c.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Moutain home base

Comfortable for 11 adults. Plenty of room to dine and congregate together. Bathrooms worked fine and good hot water. Great location for exploring many interests in the area.
Stayed 7 nights in Oct 2022
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wedding at resort

Unforeseen circumstances related to incoming hurricane weather shortened our stay. Power and water were out for a bit otherwise a really really nice place
Stayed 4 nights in Sep 2022
Verified

10/10 Excellent

maggie m.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great property

This is a spacious home, perfect for multiple Families to share! We enjoyed the multiple gathering places throughout the house, the hot tub, spacious well equipped kitchen, gas grill and hot tub! Cell service on the mountain and in the general area is extremely spotty, the house had a decent connection using the WiFi code which was a huge help! We had no problems during our stay. Beds were very comfortable.
Stayed 5 nights in Jun 2022
Verified

10/10 Excellent

Suzan K.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great house for our extended family.

Super!
Stayed 2 nights in Feb 2022
Verified

10/10 Excellent

Verified traveller

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful property!

The property was very comfortable and was only a 5 minute drive away from the ski slopes at Wintergreen. The owner was also responsive to our needs. We’d highly recommend staying here.
Stayed 4 nights in Feb 2022
Verified

8/10 Good

Sandra C.

Liked: Cleanliness, communication, location
Disliked: Check-in

Nice weekend

The property was very nice and the neighborhood was lovely. The kids with me had a great time skiing and I had a relaxing weekend in the jacuzzi. We were never able to get the lock box open for the keys, but we did find the back sliding door unlocked, so we were able to get in. We never could get the wifi to work and we could not get the TV to work properly. We were not there to really be on the internet or watch TV, so it worked out okay. I didn't realize we had to take our own trash to the dumpster, so we left it on the side porch and were charged an extra $50. It would be nice to have trashcans outside of the property and have someone take the trash. I really don't want to put trash in my personal vehicle. Overall, we had a nice time.
Stayed 2 nights in Feb 2022
Verified

8/10 Good

Gabriel G.

Liked: Cleanliness, location, listing accuracy
Disliked: Communication

All is good

A liked the house
Stayed 5 nights in Dec 2021

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