Entire home

Upscale and Family-Friendly in Wintergreen

Photo gallery for Upscale and Family-Friendly in Wintergreen

A hot tub area with wooden deck, wicker chairs, and a glass door leading to a sauna.
A deck with outdoor furniture, a fire pit, and a view of the surrounding trees.
A room with a bunk bed, a large wall mural, and several bean bags.
A spacious living room with a stone fireplace, large windows, a sofa, and a dining area.
A modern living room with a pool table, a sofa, a coffee table, and a TV mounted on the wall.

Reviews

9.6 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Family fun awaits
    Top-rated for families.
  • Beach equipment
    A rare find — beach equipment ready to go for your days by the sea.
  • Centrally-located
    You're never far from where you need to be with this convenient location.
  • Discover nearby landmarks
    Walk to Wintergreen Resort

Popular amenities

  • Spa pool on site
  • Patio
  • Kitchenette
  • Swimming pool
  • Toys
  • Barbecue

Explore the area

View map
Roseland, VA
  • Place, George Washington National Forest
    ‪1 min walk‬
  • Place, Wintergreen Resort
    ‪9 min walk‬
  • Place, Bold Rock Hard Cider Nellysford Cidery
    ‪19 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪64 min drive‬

Rooms & beds

5 bedrooms (sleeps 16)

BR1: Main level master

1 King Bed

BR2: Main level king

1 King Bed

BR3: Lower level king

1 King Bed

BR4: Lower level 2 queens

2 Queen Beds

BR5: Upper level bunk room

2 Single Bunk Beds

Living Room 1

1 Double Sofa Bed

4 bathrooms

Lower level hall bath

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Main level hall bath

Soap · Towels provided · Bathtub or shower · Toilet · Hair dryer

Master bathroom

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Upper level bunk room ensuite bathroom

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Spaces

Deck or patio
Kitchen
Kitchenette
Number of living rooms
Dining area

Add dates for prices

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  • Pool
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (180 reviews)
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About the area

Wintergreen

Located in Wintergreen, this holiday home is in the mountains. Zeus Digital Theater and Waynesboro Heritage Museum are cultural highlights, and some of the area's attractions include Wildlife Center of Virginia and Shenandoah Valley Art Center. Kayaking and fishing offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and mountain biking nearby.
View more Holiday homes in WintergreenOpens in a new window
Map
Roseland, VA

What's nearby

  • George Washington National Forest - 1 min walk - 0.0 km
  • Wintergreen Resort - 9 min walk - 0.8 km
  • Raven's Roost Overlook - 3 min drive - 2.1 km
  • Bold Rock Hard Cider Nellysford Cidery - 19 min drive - 20.8 km
  • University of Virginia - 54 min drive - 75.9 km

Getting around

  • Staunton Station - 42 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 57 min drive

Restaurants

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

Frequently asked questions

Does Upscale and Family-Friendly in Wintergreen have a pool?

Yes, this property has a pool.

How much does it cost to stay at Upscale and Family-Friendly in Wintergreen?

As of 29 October 2026, prices found for a 1-night stay for 2 adults at Upscale and Family-Friendly in Wintergreen on 3 November 2026 start from NZ$1,734, 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 Upscale and Family-Friendly in Wintergreen pet-friendly?

Yes, this property allows cats and dogs (limit 4 total).

How much is parking at Upscale and Family-Friendly in Wintergreen?

On-site parking is available at the property.

What time is check-in at Upscale and Family-Friendly in Wintergreen?

Check-in begins at 4:00 PM.

What time is check-out at Upscale and Family-Friendly in Wintergreen?

Checkout is at 10:00 AM.

Where is Upscale and Family-Friendly in Wintergreen located?

This family-friendly Wintergreen holiday home is located in the mountains, within a 15-minute walk of George Washington National Forest and Wintergreen Resort. Raven's Roost Overlook is 3 mi (4.8 km) away.

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. 34 out of 40 reviews
Rating 8 - Good. 4 out of 40 reviews
Rating 6 - Okay. 2 out of 40 reviews
Rating 4 - Poor. 0 out of 40 reviews
Rating 2 - Terrible. 0 out of 40 reviews

9.2/10

Cleanliness

9.8/10

Check-in

9.8/10

Communication

9.8/10

Location

9.6/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location, walking (hiking) distance from some great overlooks, the old Appalachian trail and a waterfall (the latter of which is just a bit farther out. Had everything you’d need for a great stay with the family and lots of space for relaxing.
Stayed 5 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Really nice place with a ton of amenities definitely recommend this place to anybody looking for a sweet getaway
Stayed 3 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was very clean and had all amenities needed for a great trip!
Stayed 4 nights in Feb 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great location to Wintergreen. The house was cozy and the hosts responsive. Great for family and friends to visit.
Stayed 3 nights in Jan 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic Stay! The home was exactly as expected and was perfect for our families. The kids had so much fun in their room and we appreciated how well stocked the kitchen & linens were. We will definitely be back!!
Stayed 2 nights in Feb 2026
Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was big,comfortable and clean. We appreciated being able to bring our pets too.The hot tub was hot but was a bit dirty. Our family enjoyed the sauna and deck area and had a wonderful stay!
Stayed 3 nights in Mar 2026
Verified review

10/10 Excellent

Liked: Check-in, communication, listing accuracy
Definitely a 5 star! We had a great stay. The house was perfect for our family, well appointed and comfortable. 15 of us skied 3 full days and the hot tub and Steam room were an added delight! We would certainly stay here again! Thank you
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
A beautiful, well-appointed house. The hot tub and sauna were fantastic. We will definitely come back!
Stayed 2 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Clean and spacious
Stayed 4 nights in Dec 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Jennifer was an amazing host. She stayed in touch and was always helpful. The property is beautiful with all the comforts of home. Would definitely recommend.
Stayed 4 nights in Jan 2026
Verified review

10/10 Excellent

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

Excellent house!

We absolutely loved our stay. Great hiking access point and very family/pet friendly. Would love to come stay again!
Stayed 3 nights in Oct 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
This home was just as promised! Comfortable, clean, and fashionable furniture and decor. Kitchen was well stocked, and the bonus fridge in the basement was a plus! Gorgeous sunset views, either on the patio or from the living room couch. Plenty of room for our multigenerational family stay. Super close to breweries, cideries, and wineries, in addition to antique stores in the cutest little towns! Highly recommend!
Stayed 4 nights in Mar 2026
Verified review

10/10 Excellent

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

Amazing place

Perfect place to get away. Much nicer than any rentals I've stayed in previously.
Stayed 2 nights in Dec 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, listing accuracy
Clean and plenty of space. Beautiful location although very high in the mtns
Stayed 3 nights in Nov 2025
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
House was amazing as shown in the photos. Plenty of room for everyone and great layout. Our kids were a little older but loved the upstairs kids lair with the rock wall. Great walking culdesac and quiet neighborhood but just a couple of minutes from the spa and gym, Frost and Fire and the slopes. I don’t want to rent this house again, I want to buy it! Great hosts and great house. Have rented nearly every year and this is the best house yet!
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

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

Great Stay in Wintergreen

We really enjoyed the house. Great location, close to the slopes and plenty of room for our two families to spread out. Thank you!
Stayed 3 nights in Jan 2025
Verified review

10/10 Excellent

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

Perfect family get away!

We had a wonderful stay. The view out of the living room was spectacular and the house had a good layout. We had everything we needed and then some. Kids had a blast! Would definitely stay again!
Stayed 4 nights in Dec 2023
Verified review

10/10 Excellent

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

Family Thanksgiving

Perfect home for a family gathering!
Stayed 7 nights in Nov 2023
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Extended family hiking trip with six adults and two young kids. The house works really well if you want a large common space but also want to give a family privacy with their own space on the lower level. The kids playroom, large dinner table for dinner and cards and hot tub/sauna were a huge hit and used everyday during our stay.
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

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

Awesome Place

Great House! We very much enjoyed our time there. We will be going back to this one again next year.
Stayed 3 nights in Jan 2024
Verified review

10/10 Excellent

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

Absolutely refreshing!

It was very nice. Beautiful home, friendly people
Stayed 2 nights in Jun 2024
Verified review

10/10 Excellent

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

Family weekend

This home was very nice with an open floor plan that worked well for our family. The game room, hot tub, and sauna were bonuses to entertain our teens…and adults as well!
Stayed 3 nights in Nov 2024
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Well appointed house and property, lots of space, all amenities included. Comms with host were timely and responsive.
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

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

Beautiful House with Beautiful Scenery

We loved the house. We stayed with our family and another family. House was great. Kids (5total) loved the bunk room. Right next to a trail with amazing views. Owner was very responsive.
Stayed 4 nights in Aug 2023
Verified review

10/10 Excellent

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

Peaceful weekend

Had a wonderful stay in Wintergreen! It was off-season, so the area was particularly peaceful. The home was very well stocked, which was important to us as a family that enjoys cooking--high-end appliances, clean/new pots and pans, properly sharp knives, etc. It's also a great home for kids--the top floor bunk bed room was a hit, as was the arcade and shuffleboard table. And it was great to be such a short walk to really nice vistas and trails.
Stayed 3 nights in Mar 2025
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