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Above the Clouds! Perfect Escape for Families!

Photo gallery for Above the Clouds! Perfect Escape for Families!

Living area
Living area
Dining
Private kitchen
Exterior

Reviews

10 out of 10
Exceptional
4 bedrooms3+ bathroomsSleeps 103200 sq ft

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning

Explore the area

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

Rooms & beds

4 bedrooms (sleeps 10)

Ground Level Bedroom

1 Queen Bed

Primary

1 King Bed

Upstairs Bedroom 1

1 Queen Bed

Upstairs Bedroom 2

2 Single Beds

3 bathrooms, 1 half bathroom

Ground Level Bathroom

Bathtub or shower · Toilet

Main Level

Toilet

Primary Bathroom

Toilet · Shower only · Jetted bathtub

Upstairs Bathroom

Bathtub or shower · Toilet

Spaces

Deck or patio
Porch or lanai
Kitchen
Dining area

About this property

Above the Clouds! Perfect Escape for Families!

Breathe in the fresh mountain air when you stay at The Retreat at Wintergreen in the Blue Ridge Mountains. This updated and spacious family-friendly home located in a quiet cul-de-sac includes two gas fireplaces, second floor deck, and a play area for the kiddos. The mountain has something for everyone from hiking, skiing, and swimming, to beer and wine tasting. The house is a short drive to the Wintergreen Spa and Lodge, and a quick walk to Devil's Knob Overlook and an Old Appalachian Trailhead.

This spacious home has two large entertaining areas. On the main level enjoy the beautiful floor to ceiling windows offering a seasonal sunset mountain view with an up-to-date kitchen. Walk out onto the second floor porch to have your morning cup of coffee while listening to nature's serenade. The main floor also includes a gas fireplace, the master bedroom and bathroom with exposed beams and an extra half bathroom.

The other entertaining space is located in the basement which has a gas fireplace along with a TV and fridge as well as another area for outdoor covered seating.. A full bedroom, bathroom, laundry room, and garage are also located on this level.

The third floor boasts beautiful exposed hardwood ceilings and a special children's nook where they can enjoy playing games, coloring, and other kid-centric activities. Two bedrooms and one bath can also be found on this level.
Our prices include all fees. No hidden fees.

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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

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, a first aid kit and a deadlock

About the area

Wintergreen

Located in Wintergreen, this holiday home is in a rural area and in the mountains. The area's natural beauty can be seen at Shenandoah National Park and Rockfish Gap Entrance Shenandoah, while Zeus Digital Theater and Wayne Theatre are cultural highlights. Wildlife Center of Virginia and War Fields are also worth visiting. Discover the area's water adventures with nearby fishing, or enjoy the great outdoors with hiking and mountain biking.
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Map
Wintergreen Resort, VA

What's nearby

  • Wintergreen Resort - 14 min walk - 1.2 km
  • Bold Rock Hard Cider Nellysford Cidery - 14 min drive - 17.1 km
  • University of Virginia - 37 min drive - 61.2 km
  • Downtown Mall - 41 min drive - 66.6 km
  • Monticello - 44 min drive - 69.5 km

Getting around

  • Staunton Station - 49 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 58 min drive

Restaurants

  • ‪Belties - ‬20 min drive
  • ‪Iron & Ale At Wintergreen Resort - ‬24 min drive
  • ‪Devils Backbone Brewing Company - ‬17 min drive
  • ‪The Market - ‬5 min drive
  • ‪The Edge - ‬6 min drive

Frequently asked questions

Does Above the Clouds! Perfect Escape for Families! have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Above the Clouds! Perfect Escape for Families!?

As of 2 Apr 2026, prices found for a 1-night stay for 2 adults at Above the Clouds! Perfect Escape for Families! on 29 Jun 2026 start from £251, 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 Above the Clouds! Perfect Escape for Families! pet-friendly?

No, pets are not allowed at this property.

How much is parking at Above the Clouds! Perfect Escape for Families!?

On-site parking is available at the property.

What time is check-in at Above the Clouds! Perfect Escape for Families!?

Check-in begins at 4:00 PM.

What time is check-out at Above the Clouds! Perfect Escape for Families!?

Checkout is at 11:00 AM.

Where is Above the Clouds! Perfect Escape for Families! located?

Situated in the mountains, this holiday home is within 1 mile (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

10

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. 22 out of 22 reviews
Rating 8 - Good. 0 out of 22 reviews
Rating 6 - Okay. 0 out of 22 reviews
Rating 4 - Poor. 0 out of 22 reviews
Rating 2 - Terrible. 0 out of 22 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Diana F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house is absolutely amazing! The host made everything so easy, and the house was very well-equipped. The check-out process was super easy! We loved it, and it's definitely among the top houses we've stayed in!
Stayed 2 nights in Feb 2026
Verified

10/10 Excellent

Andrea M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We absolutely loved our stay at Brett’s cabin. It is very spacious and clean, has 2 fireplaces and an outdoor fire pit, ample sitting areas, and had everything we needed to enjoy a weekend in wintergreen. We are hoping to return soon!
Stayed 2 nights in Oct 2025
Verified

10/10 Excellent

Hallie R.

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

Great house for families

Spacious house fully loaded with anything a family needs for a great weekend away! The house was beautiful and we enjoyed our stay.
Stayed 3 nights in Oct 2022
Response from VrboOwner on 12 Sept 2023
Thank you for the kind words. So glad you and your family enjoyed your time at the house. Come back any time!
Verified

10/10 Excellent

Sean S.

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

Family getaway

Absolutely perfect!
Stayed 3 nights in Dec 2024
Verified

10/10 Excellent

Christopher C.

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

Amazing!

The place was spectacular. Hope to be able to stay again in the future.
Stayed 2 nights in Sep 2023
Verified

10/10 Excellent

Laura B.

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

Wonderful stay at the Retreat

We had a great stay! The home was well equipped with everything we needed. The home was spacious and clean. We will definitely keep it in mind for another trip to Wintergreen.
Stayed 2 nights in Jan 2023
Verified

10/10 Excellent

Erik J.

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

Family fun weekend

This is the second time our family has stayed in this house. It was a great place for us and we hope to be back!
Stayed 2 nights in Mar 2023
Response from VrboOwner on 12 Sept 2023
We are so happy you enjoyed your time a second time! You and your family are always welcome at "The Retreat".
Verified

10/10 Excellent

Christina R.

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

Wonderful!!

This house was so great. Super clean, great location very well organized. A perfect place to spend the weekend. Our whole family loved it. Would definitely recommend highly.
Stayed 3 nights in Feb 2025
Verified

10/10 Excellent

Haley E.

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

Great place to stay

We loved our stay! The home was beautiful and clean. They had everything you need to stay with children including dishes, toys, a baby gate, etc. They even had a cute little kids rocking chair to play with. It was so nice to go and have what you need in a beautiful location!
Stayed 3 nights in Nov 2024
Verified

10/10 Excellent

Erik J.

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

Fantastic house!

This house was fantastic! It was very clean and had everything you could want readily available. We would love to return to this house in the future. It was the perfect place for our family to gather for some fall fun!
Stayed 2 nights in Oct 2022
Response from VrboOwner on 12 Sept 2023
Thank you for letting "The Retreat" be part of your family memories! We are glad you had a great time and look forward to hosting your family again soon!
Verified

10/10 Excellent

Meredith S.

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

Relaxing and Comfortable

The best part about this accommodation is all the space! Everyone had their own area to hang out. It was well stocked with everything we could possibly have needed, and the candies were a welcomed treat. Communication with the property owners was prompt and helpful. The neighbors were even cordial! Will definitely stay here again.
Stayed 3 nights in May 2025
Verified

10/10 Excellent

Ginger F.

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

Lovely. Awesome ski weekend l!

Exactly as advertised. Thank you.
Stayed 3 nights in Feb 2023
Verified

10/10 Excellent

Valerie N.

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

Delightful Holiday

This property is exactly as described and a wonderful place to relax, work, and enjoy the mountain. The home is well maintained, beautiful, and has a fully stocked kitchen to bake, cook, & entertain. We had a great time baking cookies, making dinners and having dinner around the dinner table which seats 6. Absolutely wonderful staff and great hosts! It felt like a resort inside the resort.
Stayed 10 nights in Dec 2021
Response from VrboOwner on 12 Sept 2023
Thank you so much for the very nice review. We are happy to hear you enjoyed your time at The Retreat over the holiday season. You were a fantastic guest and would welcome you back any time!
Verified

10/10 Excellent

Linda J.

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

Beautiful, large, comfortable, and convenient location

We loved our stay at this beautiful home. Everything was extremely clean, and the bathrooms and kitchen looked new. The family room furniture is so comfortable for a large group to recline and relax after a day of skiing. The kitchen was stocked with coffee k-cups, a nice double griddle pan, toaster, and Belgian waffle maker, which made family breakfast so nice and easy. We loved our stay here and had no complaints. We hope to return to the same property again—no need to look anywhere else in Wintergreen. This home had everything we wanted.
Stayed 2 nights in Feb 2023
Verified

10/10 Excellent

Andrea H.

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

Perfect Winter Weekend Retreat

My family and another family enjoyed a delightful weekend at this cabin near Wintergreen. The home is well appointed (I really appreciated the quality of the kitchen equipment) and very clean, and the layout lends itself well to two families having ample privacy and gathering space. The cabin is a five minute drive from the Wintergreen resort as well as places to sled and play in the snow, and we made wonderful memories here. I also appreciate how accessible the property manager and owner were when I needed instructions on how to re-ignite the fireplace pilot light. I feel grateful for having been able to stay here, and would absolutely return and recommend it to other families.
Stayed 3 nights in Jan 2025
Verified

10/10 Excellent

Amy H.

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

Open the door and say, WOW!

This home far exceeded our expectations!! It was perfect for our girls get-away! It’s in a beautiful and relaxing location . We spent lots of time on the large deck. They even provided s’more forks for our evening fire and dessert s’mores! They thought of everything you could possibly need and the little surprise touches were wonderful! Everything was beautiful, extremely clean and comfy (the beds, the couches and chairs)! It was very spacious and had room for relaxation, playing games, crafts, tv watching, a place especially for the kids was adorable! We had the best time and this place accommodated our every need and were already planning our next escape! Check it out and ENJOY!
Stayed 1 night in Jun 2024
Verified

10/10 Excellent

Jessica S.

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

Great house!

Wonderful house. It felt very spacious — plenty of space for our group to spread out. Big windows with beautiful views, well stocked kitchen, comfortable beds. A 5 minute drive to the skiing at Wintergreen. The owner sent us an extremely helpful pdf brochure ahead of time with very detailed information about the house. Our only challenge was with climate control — in winter, with the heat running, the living areas and master bedroom felt cool while the other bedrooms felt warm. Just keep that in mind when allocating bedrooms to the people in your party. :)
Stayed 3 nights in Jan 2024
Verified

10/10 Excellent

John D.

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

Perfect, Special, Quality Time!

We know the Wintergreen Retreat ranks as one of our best vacation homes yet! Our children and grandkids met in this beautiful mountain home for Thanksgiving as well as a birthday celebration. This house is so well appointed with.....just about everything! Not only were we able to cook Thanksgiving dinner there but just about all our other meals. We wanted especially to be "home" for dinner, so we did not miss the stunning sunsets over the mountains! And the stars at night..my goodness...amazing! The home is decorated in such a warm and comforting style. From the super comfortable, plush reclining sofas to the lovely flooring, striking windows...you just wanted to sit in that great room and take it all in! They even had some tasteful holiday decorations about that made it even more welcoming. You can see careful attention was paid to details throughout the whole, very clean house, with quality furnishing, bedding, towels etc. including current, well cared for games for both adult and children. They especially loved both the puzzle and Lego table downstairs! The owners were also very efficient and promptly answered all emails or calls. We had a minor inconvenience happen in the home through no fault of ours or the owners. They responded and made arrangements immediately, on a holiday weekend! They were also caring enough to leave some Happy Birthday balloons and chocolates for the birthday celebration. Wintergreen property is AMAZING! So many opportunities to hike right in Wintergreen. A favorite was the Shamokin Waterfall hike..so pretty! We also went off property to striking Crabtree Falls. That was also amazing! All in all..a fabulous home, perfect holiday, birthday, quality time spent, and precious memories made in such a beautiful setting. So thankful for that experience!
Stayed 6 nights in Nov 2022
Verified

10/10 Excellent

Kristen H.

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

Great stay!

We had a fabulous stay. The house was clean and very accommodating for 8 friends. Very spacious and had everything we needed! Thanks!
Stayed 2 nights in Nov 2022
Verified

10/10 Excellent

Norma A.

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

Excellent

Our family loved this Wintergreen retreat. It was beautiful, clean, comfortable, and well stocked. We would definitely go there again.
Stayed 2 nights in Oct 2022
Verified

10/10 Excellent

Kate N.

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

Definitely Going Back

We had a great experience at The Retreat! Check in was easy and Brett's communication was great and answered all of our questions in a timely manner. You can tell the house has been well maintained and cared for. It was better than we expected, we will definitely be back!
Stayed 1 night in Jul 2022
Verified

10/10 Excellent

Debra S.

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

A place above the clouds!

Thank you for sharing your wonderful home with my family. We were finally able to be together after 2 years, due to Covid-19. The attention to detail in the house made it feel like a home away from home. You provided everything anyone would need, plus so much more! The kids loved the surprise candy in the refrigerator. It wasn't always the best weather, but the house had more than enough room to pass the time together. The family was able to do some tubing, hiking and other activities that were offered at the resort. A thoughtful gesture by you providing our New Year's Eve box. We celebrated at the Wintergreen Resort, which had amazing fireworks! Once again, thank you Brett for promptly answering my many questions. We haven't stopped talking about our time together. Would love to come back someday.
Stayed 5 nights in Dec 2021
Response from VrboOwner on 12 Sept 2023
Debra, thank you so much for the kind words. We are so happy your family had a wonderful time together and we hope you come stay again soon!

About the host

Hosted by Brett Sullivan

Host profile image
Hi my name is Brett. My family and I enjoyed visiting Wintergreen and the Blue Ridge Mountains so much we decided to make it permanent with a second home. We love exploring all of the different outdoor activities and supporting the local business along the 151 corridor. I look forward to working with you to ensure you enjoy it just as much as us.

Why they chose this property

This property is where memories are made! There is space dedicated for large groups but also when the kids want to watch a movie they can scamper downstairs to have their own time and space. Additionally, this house is located in a secluded area near the Devil's Knob Overlook at Wintergreen, which allows you to hear nothing but birds chirping and the wind blowing through the leaves. This house has also been lovingly maintained and you can see that in the craftmanship and cleanliness throughout the property.

Premier Host

They consistently provide great experiences for their guests
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