Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

Wintergreen Resort, Virginia
$231 avg/night
Minimum Stay 2 Nights
Bed 2

Bed

Bath 2

Bath

Home Condo

Property Type

Sleep 6

Max Sleeps

Night 2 nights

Min Stay

2 bedroom 2 bath and a queen sofa bed. Sleeps 4-6 very comfortably.
This is our second condo here as we’ve fallen so in love with Wintergreen as a four season resort.
(Dobie is our other condo also 2/2 with Queen Sofa bed next to the Mountain Inn also ski in ski out ~ beginner slope
VRBO property ID 7973682)

Welcome home to the Highlands. Overlooking the advanced Black Diamond ski Slope.
Read all of my description here for lots of information if you are new to the area...
Take your vacation up a few notches in our thoughtfully curated space.
Feel instantly relaxed when you step inside and see the never ending backdrop of vast peaks and valleys.
Newly renovated with fresh finishes throughout. Both bedrooms have brand new carpet, mattresses and bedroom furniture & closet with plenty of hangers provided. Brand new tile flooring in each bathroom as well. We offer central heat and a/c or grab some readily available fresh cut firewood and cozy up by the fireplace. We have a full size washer and dryer, laundry basket, lint rollers, iron and ironing board etc.
Our condo sleeps 6 very comfortably with a *Queen sofa bed in the living room. You’ll find 2 full bathrooms, a shower in the primary/King bedroom and a shower/tub in the guest bath. Queen guest bedroom - Stream your favorite show or movies on any of the 3 smart tv’s in king bedroom, guest bedroom & 65 inch smart tv in family room- 3 TVs total.
Highlands is our personal condominium when we visit Wintergreen and it is cleaned and sanitized thoroughly as we would our own home and according to recommended guidelines prior to every check in.

Plenty of extra linens, Bath Towels, dish towels and essential paper products including paper towels, hand soap, TP, garbage bags etc. restocked prior to every check in. Keurig K-cup and standard coffee pot and filters provided so you can brew a pot of your favorite coffee or bring your favorite single use K-cup flavor. Whether you’re meeting up with friends or spending time with family- take a break from the hustle and bustle atop this beautiful Mountain Resort.

*While we are home owners in Wintergreen we are no way affiliated with Wintergreen Inn Resort- you as our guests staying in our Wintergreen home have access to the Chestnut Springs outdoor Pool & Pavilion seasonally- *We are Not Club members and do Not have access to the indoor pool or fitness center so if you are wanting to use these two facilities we graciously ask that you please “Do Not” book with us as we are not able to offer access.

New to Wintergreen Take a moment and Google “Wintergreen Resort” for real time current events and download their App- as there's almost always something fun happening on the mountain!

Our Highlands condo is just a short walk across the street to the newest eatery on the mountain “Fire @ Frost” for all things gourmet pizza. We have many lovely hiking trails or a short drive to local state parks, several wineries, breweries, restaurants & antique stores.
Historic “Monticello” the Estate of Thomas Jefferson has reopened with enhanced cleaning and safety measures in place- they offer a beautiful garden and tours of the estate & are family friendly-located in nearby Charlottesville. Check out Blue Ridge Fruit Loop- we love Strawberry picking nearby as well.

Shenandoah National Park is just a short drive and
Devils Backbone restaurant and brewery, Blue Mountain Restaurant and Brewery, Blue Toad Hard Cider Brewery & Bold Rock Cidery are a few of the local faves & just 15 min drive from the condo.

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

Feature Features

  • SKI

    Close To Skiing Ski-in/ski-out Access
  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    2 Bedrooms Bed Sheets Provided Sofa Bed
  • KITCHEN

    Coffee/tea Maker Dishwasher Ice Maker Microwave Oven Paper Towels Refrigerator Spices Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Onsite Parking Wheelchair-accessible Parking Available
  • INTERNET

    Free WiFi, With Speed Of 500+ Mbps (good For 6+ People Or 10+ Devices)
  • OUTDOORS

    Balcony Outdoor Furniture
  • POOL/SPA

    Outdoor Pool
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Fishing Nearby Golf Nearby Hiking Nearby Hiking/biking Trails Nearby Kayaking Nearby Snow Sports Gear Winery Tours Nearby
  • ENTERTAINMENT

    Books Games Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Playground
  • LOCATION HIGHLIGHTS

    In The Mountains
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    1 On-site Accessible Parking Spaces If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Upper Floors Accessible By Stairs Only Wheelchair-accessible Parking

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 6

Map Map

School District Availability

Review Review

  • amy

    Submitted Feb 7, 2026

    Stayed Jan 30, 2026

    Clean, cute condo and Mountain View is amazing

  • Tama

    Submitted Jul 9, 2023

    Stayed Jul 7, 2023

    Beautiful condo. Very clean and the kitchen is well stocked with equipment. The view is awesome. The beds were comfy. The condo is modern and has great seating both inside and on the balcony. Would definitely stay there again.

  • Ben C.

    Submitted Apr 13, 2026

    Stayed Apr 10, 2026

    We loved our stay and would love to return. Great view. Very clean and well appointed.

  • Grant N.

    Submitted Feb 24, 2026

    Stayed Feb 20, 2026

    Great condo!

  • ERIC M.

    Submitted Jan 31, 2026

    Stayed Jan 25, 2026

    This condo is fantastic! The place was super clean and comfortable with amazing views of the mountain valley below. We were there to ski and the easy access to the Highland Chair Lift just behind the condo was really convenient. The condo was well stocked with the essentials, which was appreciated, and host was super accommodating and responsive. We were scheduled to arrive during a snow storm and the host made arrangements to allow us to check-in a day early to beat the weather. We had a great stay and will definitely be back!

  • Joel H.

    Submitted Jan 12, 2026

    Stayed Jan 4, 2026

    Second time staying at the Condo in Wintergreen. The location is perfect, space immaculate, and beautiful. The condo has all you will need. Perfect for a get away.

  • Jason M.

    Submitted Jan 5, 2026

    Stayed Dec 29, 2025

    The condo was warm, welcoming, with a spectacular view. The access to the resort was easy to get to providing us with more time on the slopes . The condo was also walking distance...even in the cold weather to the bake-house where we got pizza, cookies and some hot chocolate. The check in was easy and though I didn't get to respond to Niquita quickly she was ever present asking about our stay during the stay. Sorry, I was having fun . When we come to wintergreen again we will most certainly be staying there.

  • Jake M.

    Submitted Dec 30, 2025

    Stayed Dec 21, 2025

    Had a great ski trip

  • Kathryn O.

    Submitted Dec 5, 2025

    Stayed Nov 28, 2025

    The host was very responsive. The condo had beautiful views and was maintained well. We had a great stay!

  • Bill B.

    Submitted Nov 28, 2025

    Stayed Nov 21, 2025

    Beautiful condo and well maintained. Everything was as advertised. Great host. Very pleased with the entire experience.

  • Kellie S.

    Submitted Nov 11, 2025

    Stayed Nov 7, 2025

    Great location and great stay

  • Anthony M.

    Submitted Nov 6, 2025

    Stayed Nov 2, 2025

    The space is great with every amenity you would need. The host was wonderful and super responsive. I would highly recommend and will be booking with the host again.

  • Leslie H.

    Submitted Oct 20, 2025

    Stayed Oct 17, 2025

    What a great spot! Parking is just outside the door, access is easy, and the condo was spotless. The balcony and view of the black diamond courses was stunning, we spent so much time out there! Hiking and dining are nearby, and the kitchen has everything we needed to cook breakfast and dinner when we chose to stay in. We can’t wait to visit again!

  • Brandon G.

    Submitted Oct 12, 2025

    Stayed Oct 10, 2025

    We have been to Wintergreen too many time to count and this was by far our favorite place we’ve stayed. The views were gorgeous and the place was immaculate. It was overall a very comfortable stay. You will not be disappointed staying there.

  • melissa a.

    Submitted Oct 5, 2025

    Stayed Oct 3, 2025

    Had another awesome stay! The weather was great. The sunrises and views were amazing. The condo is equipped with everything you need. Very clean. Decorated very nicely. Look forward to another visit soon!

  • Kelly F.

    Submitted Sep 22, 2025

    Stayed Sep 20, 2025

    Beautiful view! Clean and Comfortable ,everything you would need! So quiet this time of year.Would repeat this condo again!Owner very attentive!

  • Sandra T.

    Submitted Sep 6, 2025

    Stayed Sep 2, 2025

    Beautiful condo with gorgeous views of the mountains. Everything clean and comfortable. Host is awesome. We will be back.

  • s g.

    Submitted Sep 5, 2025

    Stayed Aug 29, 2025

    Perfect location. Magnificent view. Great furniture. Remodeled unit - very nice. Very clean. Only down side was we had to buy toilet paper, paper towels, soap for shower and dishwasher soap (for a 3 night stay). Hand soap dispenser was broken in bathroom And I missed that a blow dryer is not provided. Would return but bring supplies. View of sunrise from porch.

  • Debbie O.

    Submitted Aug 26, 2025

    Stayed Aug 22, 2025

    The condo was beautifully decorated, and the view from the balcony was spectacular! The condo was meticulously clean and had most everything we needed. It would have been nice to have bedside table lamps in the queen bedroom. Also, the lamps in the king bedroom above the bed, appeared to have a very weak battery and did not provide sufficient light for reading. Those were minor things. The owner of the condo was pleasant and accommodating. I would definitely stay at that condo again!

  • Kisha C.

    Submitted Aug 21, 2025

    Stayed Aug 15, 2025

    Relaxing with beautiful views.Decor was beautiful and comfortable. Anything you could possibly need was available! Highly recommend.

  • Stewart B.

    Submitted Aug 13, 2025

    Stayed Aug 6, 2025

    Great view. Well furnished. Very comfortable.

  • Ben A.

    Submitted Aug 5, 2025

    Stayed Jul 22, 2025

    One of the most comfortable and clean property we stayed in. We had a great time and enjoyed the view!

  • Submitted Jul 21, 2025

    Stayed Jun 27, 2025

    We enjoyed our stay at the condo. Our host was very responsive to any request. It's obvious she wants her guests to be happy. It's located in a very accessible area of the mountain. We would definitely stay again.

  • Scott R.

    Submitted Jun 22, 2025

    Stayed Jun 20, 2025

    We’ve stayed at several places at Wintergreen and this was definitely the best. Very nicely remodeled inside and very clean. By far the best view from balcony that we’ve ever had at Wintergreen. Would highly recommend this condo and would love to stay again in the future.

  • melissa a.

    Submitted Jun 16, 2025

    Stayed Jun 13, 2025

    We had a fabulous stay! The view is amazing. The condo is perfectly appointed. Everything needed is on hand. Great location. We will definitely be back! Thank you for sharing such a great place!

  • Vicki K.

    Submitted May 27, 2025

    Stayed May 23, 2025

    We go away Memorial weekend to celebrate our daughter's birthday. Wintergreen is a beautiful area and the condo is like home away from home. It has everything we need.

  • Michael F.

    Submitted May 18, 2025

    Stayed May 15, 2025

    Probably the best VRBO we have ever stayed in! Perfectly clean and well appointed! Definitely recommend to everyone!

  • Leanne K.

    Submitted May 12, 2025

    Stayed May 7, 2025

    If I could give this property a rating higher than 10 out of 10, I would. First of all, the listing is 100 percent accurate. It very accurately describes the property and it gives all the details that a traveller needs to know on arriving. The condo is very well maintained and equipped. The owners have a great attention to detail and have included lots of extras like a laundry basket, hangers, extra blankets, etc. The kitchen is very well equipped for self-catering; dish soap and dishwasher detergent are provided; the tea towels are new and a new sponge was provided for washing up. There is also wood provided for the log burner although it was too warm for a fire while we were there. It is a comfortable and well-maintained property. Also, it is spotlessly clean. The cutlery is clean; the glasses are clear; the bedding is new and clean; the bathrooms are clean; the floors are clean. This is a rare and special place. And if that isn't enough, the location is incredible. It is a very quiet resort with spectacular views of mountains and valleys. The sun rises over the mountains and there is a spectacular sunrise every morning. The only noise we heard was the singing of birds. It is located very close to the Blue Ridge Parkway and is conveniently located (less than an hour) to Liberty University. It is a great mountain escape. I would definitely stay here again.

  • Chad R.

    Submitted Apr 15, 2025

    Stayed Apr 13, 2025

    The place is beautifully decorated. Quality everything. Kitchen well equipped. View is amazing! Cant wait to visit again.

  • Catherine T.

    Submitted Mar 23, 2025

    Stayed Mar 21, 2025

    We were so happy with this Highlands condo. Such a peaceful place, beautiful mountain sunrise views, and a very clean and well-appointed space. The happy surprises just kept coming, exactly as in the listing. And the beds were sooo comfortable. :)

  • Melanie W.

    Submitted Mar 12, 2025

    Stayed Mar 7, 2025

    Wonderful, quiet condo with plenty of space and amenities. Gorgeous mountain views!

  • chad k.

    Submitted Mar 2, 2025

    Stayed Feb 28, 2025

    Absolutely beautiful place for our family. We had the best time. Incredibly gracious hosts matched only by the view and proximity to the slopes. Be mindful of the local police. 25 MPH means 25

  • Whitney S.

    Submitted Feb 24, 2025

    Stayed Feb 20, 2025

    Our stay was amazing! The unit was spotless and fully stocked. We were able to communicate with the owners and receive quick responses. The view is spectacular! Highly recommend!

  • Lloyd F.

    Submitted Feb 18, 2025

    Stayed Feb 14, 2025

    Wonderful condo in the Highlands complex. High end finishes and decor. Great views. You can walk to the Highlands ski slopes from this unit.

  • Clint S.

    Submitted Feb 13, 2025

    Stayed Jan 31, 2025

    Check in was easy, condo was great, mountain views were amazing and ski-in/ski-out location was awesome. Would recommend.

  • Julie S.

    Submitted Feb 10, 2025

    Stayed Feb 8, 2025

    This is a beautiful condo, well appointed on the inside. And we were very pleased with its location, given it’s proximity to both the slope access and the spa.

  • Karen Yanting T.

    Submitted Feb 4, 2025

    Stayed Jan 17, 2025

    We had a great time staying at WinterGreen for a week during the MLK holiday, and this house deserves a five-star review. In addition to being satisfied with the location, interior decoration, and cleanliness, seeing the sunrise every morning on the balcony was also our most pleasant surprise and favorite. This is a place we will come back to.

  • Kathleen B.

    Submitted Jan 27, 2025

    Stayed Jan 24, 2025

    We have stayed in multiple places over the years and this by far is one of the best!! It was in a great location not only for skiing, but a spectacular view. It was absolutely clean and had everything we needed for cooking etc we will recommend and definitely be back. Thank you!!

  • Sandra C.

    Submitted Jan 12, 2025

    Stayed Jan 10, 2025

    We loved this condo! Great views, cleanliness and price!!!

  • Jenni S.

    Submitted Jan 6, 2025

    Stayed Jan 3, 2025

    Weekend ski trip with mom and three teens. Everything you need and a comfortable and very clean condo. Nicely updates with all amenities. Close to the ski resort and as easy as can be. Thank you so much! We will be back!Jenni

  • Emily A.

    Submitted Jan 3, 2025

    Stayed Dec 26, 2024

    This is an immaculate and well-equipped condo in the Wintergreen resort community. It has a spectacular view and great communication with the owner. I highly recommend it!

  • Michael C.

    Submitted Nov 30, 2024

    Stayed Nov 26, 2024

    We have stayed in quite a few condos at Wintergreen and this condo has been our favorite. The condo was extremely clean and had every amenity you would expect at a VRBO. View is amazing as expected. We highly recommend.

  • Debbie D.

    Submitted Nov 11, 2024

    Stayed Nov 8, 2024

    We had fun checking out the area hikes and breweries!

  • Janelb62

    Submitted Nov 7, 2024

    Stayed Oct 25, 2024

    Condo is very clean. King bed was super comfortable! Great views…great condo!

  • Pam M.

    Submitted Oct 24, 2024

    Stayed Oct 18, 2024

    Highlands Condo was great. Amazing views, cozy accommodations and everything we needed for our family to enjoy a weekend away! The owner checked in on us during our stay to make sure everything was OK. We'll choose this spot again if we are going back to Wintergreen! :)

  • Cathy M.

    Submitted Oct 14, 2024

    Stayed Oct 10, 2024

    This is the 2nd time we’ve rented this condo at Highlands and we love it. The condo has been completely renovated and is one of the nicest rentals we have experienced in Wintergreen. Each Fall we enjoy apple picking, hiking, leaf viewing, wineries, breweries and art festivals. It is our happy place. We will rent this condo again.

  • melissa a.

    Submitted Oct 7, 2024

    Stayed Oct 4, 2024

    Had a nice Fall weekend getaway-the condo was amazing, awesome view, great location and was beautifully equipped. Will definitely be coming back! Thank you for sharing this great place!

  • Shana S.

    Submitted Sep 29, 2024

    Stayed Sep 27, 2024

    We had an amazing time at Highlands! The view was even better than advertised, it was great having all of the detailed info in the description. All amenities you could need. Great hiking, breweries, and vineyards near by! The resort has everything you could need. Highly suggest looking into having dinner at Farmhouse at Veritas!!! I may have missed it in the description, but make sure you bring your own shampoo, conditioner and soap for the shower!

  • Renee H.

    Submitted Sep 2, 2024

    Stayed Aug 30, 2024

    We loved the location of your condo. The sunrises are some of the best we have seen.

  • Vicki R.

    Submitted Aug 2, 2024

    Stayed Jul 25, 2024

    My friend and I stayed in the condo for the Racquet Wars tennis tournament. Gorgeous! The condo is in impeccable condition. It was the perfect space for the two of us and would be more than comfortable for two couples. The balcony was wonderful for breakfast and evening drinks. The location is fantastic....super close to the Devils Knob tennis and golf center (walking distance), the Fire and Frost restaurant which you don't want to miss (even closer walking), and a quick drive down to The Market for some fantastic sandwiches. Niquita was a wonderful host, checking in with us to make sure we had no issues with check in and everything was going smoothly. The beds and pillows were incredibly comfortable and I can be a little picky about that and have had some terrible experiences, but not here. Great night's sleep! We will definitely stay here again!

  • Steve L.

    Submitted Jul 21, 2024

    Stayed Jul 19, 2024

    Nice place and very clean. Views are wonderful. I’ve stayed at other VRBOs where they wanted us to sweep, wipe counters, take out garbage, etc. it was great this owner just wants you start dishwasher and turn down the ac. Perfect! After all we do pay a cleaning fee. Easy short walk to trails, pizza shop and resort restaurants. Would definitely stay here again.

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Total

Includes taxes and fees
$227+
View details