Game Room, Sauna, Bonus Apartment Near Wintergreen Resort!

Nellysford, Virginia
$604 avg/night Minimum Stay 2 Nights
Bed 6

Bed

Bath 4

Bath

Home Private Vacation Home

Property Type

Sleep 20

Max Sleeps

Night 2 nights

Min Stay

Hillside Hideaway at Wintergreen

Your perfect mountain retreat awaits in Virginia’s scenic Valley & Ridge Region!

A Home Designed for Every Occasion

Leave the hustle and bustle behind and escape to Hillside Hideaway, a unique and spacious mountain home nestled in the breathtaking landscape of Wintergreen. Known for its stunning vistas and year-round outdoor activities, Wintergreen offers the ideal setting for an unforgettable getaway.

Fully Equipped Kitchen: Perfect for preparing hearty meals for family and friends.
Cozy Living Spaces: Expansive windows provide stunning views and fill the home with natural light.
Recreation Room with Private Bar: Unwind with a game of pool or enjoy a drink at your private bar.

The property features six bedrooms and four-and-a-half bathrooms, with enough space to accommodate up to 18 guests comfortably:

Main House: Five bedrooms and three-and-a-half bathrooms.
Apartment-Style Living Space: Located above the garage, it includes three beds and one full bathroom, offering additional privacy for large groups or multiple families.
Unwind in Nature

Step outside and soak up the beauty of the Blue Ridge Mountains:

Relax on the screened porch with your morning coffee.
Take in the stunning views from the expansive deck.
Retreat to the sauna for ultimate relaxation.
Exciting Adventures Await

Located minutes from Wintergreen Resort, Hillside Hideaway offers year-round activities:

Winter Adventures: Skiing, snowboarding, and snow tubing.
Summer Fun: Golfing, hiking, and swimming at nearby Lake Monocan (public access available daily except Saturdays; additional membership fees apply).
Local Hiking: Explore nearby trails like Crabtree Falls or Spy Rock for incredible views of Virginia’s wilderness.

After a day of exploring, unwind at one of the region’s favorite breweries or wineries along the Nelson 151 Trail, including Blue Mountain Brewery, Veritas Vineyard & Winery, and Bold Rock Hard Cider.

Proximity to Educational Institutions

For those visiting local colleges, Hillside Hideaway is conveniently located near:

University of Virginia: Approximately 30 miles away in Charlottesville.
James Madison University: Approximately 50 miles away in Harrisonburg.




Property Highlights
Newly added EV Charger
6 Bedrooms
4.5 Bathrooms
Game Room with Private Bar
Sauna
Screened Porch
Expansive Deck with Mountain Views
Garage with Upper-Level Apartment-Style Living Space
Keyless Entry
Important Rules

To preserve the tranquil atmosphere of the area, the following community rules are strictly enforced:

Quiet hours: 8 PM - 8 AM
No loud music, drone use, or parking on neighboring lands.
Trespassing on neighboring properties is prohibited.
Occupancy limits are strictly enforced to prevent parties or gatherings.
Booking & Cancellation
Check-In: 4:00 PM (keyless entry begins at this time).
Check-Out: 10:00 AM.
Guests may cancel up to 30 days before arrival for a refund (administrative fees and insurance are non-refundable). Optional Cancel For Any Reason and Standard Travel Insurance are available for purchase.

Book your stay at Hillside Hideaway today and experience the perfect blend of relaxation and adventure in Virginia’s stunning mountain landscape!




Note:  This home is in the mountains and is subject to seasonal weather and other natural changes. It is likely this home may occasionally experience insects, arachnids, and other wildlife. Preventative treatments are performed regularly, and guests can help reduce encounters by keeping food sealed and minimize light exposure at night. As this is part of the natural setting, refunds or moves are not offered for such occurrences. Please consider this before booking.

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  • Feature Features
  • Map Map
  • School District Rates & Availability
  • Review Review

Feature Features

  • SKI

    Close To Skiing
  • PETS

    No Pets Allowed
  • SAFETY

    Carbon Monoxide Detector Not Reported (host Has Not Indicated Whether There Is A Carbon Monoxide Detector On The Property; Consider Bringing A Portable Detector) Smoke Detector Not Reported (host Has Not Indicated Whether There Is A Smoke Detector On The Property)
  • BEDROOM

    6 Bedrooms
  • GENERAL

    Unit Size: 4406 Sq Ft (409 Sq M)
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine
  • PARKING

    Electric Car Charging Station On Site Onsite Parking
  • INTERNET

    Internet Access
  • OUTDOORS

    Barbecue Grill Firepit Patio
  • POOL/SPA

    Sauna
  • BATHROOMS

    4.5 Bathrooms Bathtub Or Shower Hair Dryer
  • THINGS TO DO

    Fishing Nearby Golf Nearby Hiking Nearby Hiking/biking Trails Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Foosball Table
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 20

Map Map

School District Rates & Availability

Review Review

  • Leslie

    Submitted Nov 12, 2022

    Stayed Nov 4, 2022

    Loved the house and space. We didn't see the garage door opener the first night, and attempted the code listed on the sheet for the garage, and it didn't work. We needed that extra bedroom, and even though the call was answered saying someone would call back within 20 minutes, no one ever called back. The next day we found the garage door and texted to let them know. The only other problem we encountered was a patio door that was unlocled when we arrived, but the lock was broken and did not work. Otherwise, everything was great!

  • Tara Cohee A.

    Submitted Feb 3, 2026

    Stayed Dec 26, 2025

    We had a wonderful stay with our extended family. Our only issue was the water, it never seemed to get hot enough. We did let them know and they were planning to address it, it just didn’t happen before we left.

  • Janine B.

    Submitted Dec 14, 2025

    Stayed Dec 12, 2025

    We needed to gather as a family just for the weekend and it was perfect..the younger ones want to come back to enjoy the area next

  • Christopher C.

    Submitted Aug 17, 2025

    Stayed Aug 15, 2025

    Great stay with plenty of room

  • Tanesha W.

    Submitted Aug 10, 2025

    Stayed Aug 6, 2025

    We loved every part of the house and surroundings. It was a wonderful experience and would absolutely do it again.

  • Doreen C.

    Submitted Aug 10, 2025

    Stayed Jul 25, 2025

    My family of 15 were in Nellysford for a family event and the size of the house was perfect for our group. The layout was great for our family with my grandsons in the bunk room. The game room was also perfect for them to hang out. Plenty of inside space to meet our needs. The house was well stocked with kitchen items and inside was clean. Screened porch wasn’t really useable without a good cleanup from leaves and debris. Outdoor space was very limited. Parking was a bit difficult to maneuver cars in and out of narrow driveway. The AC wasn’t working properly and we froze our first night. It was set too low and was not able to be adjusted. We had to turn the unit off to make it bearable. Maintenance company didn’t come on Saturday instead just sent me a message with a picture telling me how to adjust, which I already knew. If someone had come they would have known that and they could have gotten it fixed on Saturday instead of having to wait until Monday. We had to spend the entire weekend turning ac on and off to maintain a comfort level. I am still waiting for a response to my request for a reimbursement for our inconvenience. It was difficult not having one person to call if we had a problem.

  • Felicia G.

    Submitted May 26, 2025

    Stayed May 23, 2025

    This was the most ideal location for what we needed for our bachelorette party. It was in close distance to the wineries we went to, and it comfortably fit all of us. There were 18 that stayed in the house, and there wasn’t a moment where we felt like we were all on top of each other. It was a stunning house in the middle of a beautiful location where we all felt safe and happy.

  • Cindi S.

    Submitted Apr 19, 2025

    Stayed Apr 11, 2025

    There was so much to do, you don’t have to leave the place. However, it’s a great area to explore as well.

  • Evangeline H.

    Submitted Apr 3, 2025

    Stayed Mar 27, 2025

    Great spot for a bachelorette weekend! Plenty of room

  • Elizabeth H.

    Submitted Feb 24, 2025

    Stayed Feb 14, 2025

    This was the perfect house for our group of 9 adults and 3 children to celebrate our parents' 75th birthdays. The kitchen was well equipped, we loved the pool and foosball tables, and the table was big enough to fit all of us. The extra room above the garage came in handy, as well. We enjoyed being close to hiking trails, breweries, and other fun things close by. We've bookmarked this house for future family gatherings!

  • Beth C.

    Submitted Nov 5, 2024

    Stayed Oct 29, 2024

    Our daughter got married at Silver Fox Lavendar Farm and this was the perfect retreat for the whole family! It is a wonderful space. Would love to return.

  • Freda N.

    Submitted Oct 23, 2024

    Stayed Oct 17, 2024

    Cleanliness… better than average Needs TLC in replacing burned out bulbs: lamps, inside fridge, over the stove. Mattress in MBR main level terrible. Others fair. Great house…. Needs some TLC

  • Dana M.

    Submitted Sep 23, 2024

    Stayed Sep 20, 2024

    Spacious, well-equipped home with lots of space and nice touches, such as the bar/game room as well as the cozy living room area. Had a wonderful stay. The only thing that would prevent me from returning to this place is the trash removal situation. It was very inconvenient to have to gather up all of our trash for the 3 night stay and haul it away, especially without trucks. Additionally, the fact that the trash place wasn't even open on our check-out date made it that much more inconvenient. This really needs to be addressed, as this is a service that should have a MUCH better process, given the expense of the house/service fees.

  • Mark K.

    Submitted Sep 9, 2024

    Stayed Sep 5, 2024

    Enjoyed the stay in this unique property. Kitchen was fully stocked and worked well for our group. Also enjoyed large clubroom / bar area. We would rent this house again.

  • Amy H.

    Submitted Jun 26, 2024

    Stayed Jun 17, 2024

    Good time. Suggestion: instructions re: the pool are very vague and where to find the key on the fridge also vague. Need to clarify # of guest and location of key. (keychain in magnetic basket on fridge) Need a new outdoor rug under fire pit. Lots of crickets!!

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Total

Includes taxes and fees
$604+
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