Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Wintergreen Resort, Virginia
$252 avg/night
Minimum Stay 1 Nights
Bed 2

Bed

Bath 2

Bath

Home Condo

Property Type

Sleep 8

Max Sleeps

Night 1 nights

Min Stay

Updated 2 bedroom/2 bathroom slope-side condo with amazing mountain views. Short walk around the building gets you to our door! Slope side to enjoy the best of Wintergreen skiing in the winter months or for hiking and mountain adventures during the rest of the year. View the fireworks from your private balcony on the 4th of July and New Years. Located in the heart of Wintergreen and high atop Upper Diamond Hill, it is convenient for skiing, dining, hiking and just relaxing with some of the most beautiful views.

Prime, High Demand Location
With just a short 5 minute walk to Mountain Inn, restaurants, shops, and concerts, this is the perfect slope-side getaway.

Enjoy your morning tea or coffee on the deck overlooking the breath-taking mountain sunrises or your sipping your glass of wine as the day winds down and the last light illuminates the slopes with the amazing colors. Catch the best views the mountain has to offer with amazing private fireworks views from the deck.

Gated (during peak demand) slope-side parking right in front of the condo reserved for our Diamond Hill guests.

The space
High end updates top to bottom finish this space off in grand splendor. Our well appointed condo is furnished with all the comforts of home that you'd want from preparing meals to relaxing in front of the wood burning fire or watching the 65 TV after an amazing day on the mountain. Our bedrooms are furnished with high end comfortable beds and linens. We have a washer and dryer and provide laundry detergent, dish detergent, dish washer detergent, paper towels, toilet paper and hand soap. With conveniently located USB outlets throughout the condo, your devices are always charged up and ready to go!

The second bedroom has a Twin XL over Queen bunk bed with a Twin XL trundle. Other exciting updates on the horizon include massage chair, arcade game and foosball table.

The living room is equipped with Queen and Twin Sleeper sofas with upgraded gel foam mattresses (installed for stays after 10/26/2022) to allow for maximum flexibility for your sleeping arrangements.

Personal code electronic door locks on the condo and ski locker to relieve you of the worry of losing keys while out shredding up the mountain. No more coordinating with others in your party to get into the locker at the end of the day!

Note: No access to resort amenities (gym, indoor pool, racquet courts) granted with rental.

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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 Cookware/dishes/utensils Dishwasher Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking
  • INTERNET

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

    Balcony
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Towels Provided
  • WORKSPACES

    Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Fishing Nearby Fitness Center Golf Nearby Golfing On Site Hiking Nearby Hiking/biking Trails Nearby Sledding Nearby Swimming Nearby Wildlife And Game Walks Nearby Winery Tours Nearby
  • ENTERTAINMENT

    Arcade/game Room Foosball Table Games Smart TV
  • LIVING SPACES

    Fireplace
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Travel Crib
  • LOCATION HIGHLIGHTS

    In A Village In The Mountains
  • 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 : 8

Map Map

School District Availability

Review Review

  • Mike-Anthony

    Submitted Jun 17, 2023

    Stayed May 11, 2023

    5 STARS will stay at again!!!!!

  • Blayre G.

    Submitted Feb 18, 2026

    Stayed Feb 13, 2026

    Very organized information and amazing communication from host ahead of arrival; the view and location are amazing, and the accommodations were comfortable and made for an easy and fun adventure! Will definitely stay here again.

  • Joe A.

    Submitted Feb 12, 2026

    Stayed Feb 9, 2026

    Everything was as advertised. Great location.

  • Chris S.

    Submitted Feb 5, 2026

    Stayed Jan 22, 2026

    It was perfect and as described! Great location, great view of one of the main ski runs. Seemed to be updated recently and super clean! The massage chair is a GREAT Touch after you are done skiing. Couldn't recommend this place any higher, It was Great!

  • Susan J.

    Submitted Jan 10, 2026

    Stayed Jan 5, 2026

    Amazing spot! Ski in - out was so convenient and a quick walk to the village! Phyllis was amazing and the condo was beautiful! Would definitely book this condo again!

  • Susie P.

    Submitted Jan 4, 2026

    Stayed Dec 19, 2025

    The unit was in great condition and clean. Excellent views and ski in/ out was great to have.

  • Patrick E.

    Submitted Jan 2, 2026

    Stayed Dec 30, 2025

    Amazing Condo and owner. Great access to slopes, well appointed and clean. Beautiful views and can walk to everything in the heart of the resort

  • Emily H.

    Submitted Dec 30, 2025

    Stayed Dec 26, 2025

    Unit was well appointed with essentials and kitchen was well stocked!

  • Daniel W.

    Submitted Nov 10, 2025

    Stayed Nov 8, 2025

    Great

  • Dave S.

    Submitted Mar 20, 2025

    Stayed Mar 6, 2025

    The nicest places we’ve stayed. Ski in / ski out. Walkable to entire village. That massage chair was a dream

  • Meredith G.

    Submitted Mar 4, 2025

    Stayed Feb 28, 2025

    The location is very convenient with amazing views of the slopes and terrain park.

  • Allison Packer C.

    Submitted Feb 4, 2025

    Stayed Jan 23, 2025

    We came for a weekend of family skiing. The condo was beautiful, clean, and had so many fun touches. The location right on a green slope cannot be beat. The kitchen had everything we needed. The view was spectacular. And the massage chair was divine. I would definitely recommend and would be thrilled to stay again in the future.

  • Brittnay S.

    Submitted Jan 11, 2025

    Stayed Jan 6, 2025

    So for those of you asking “how far from the slopes?” It is literally 90 paces (for a 5’5” momma) from door around the unit, to put on your skis. Easy peasy. You want to cook for your kiddos? it’s all there. Coffee set up, 3 pans of varying sizes, glassware to cook brownies. Tupperwares to store stuff during your stay. Bring a cooler and plan meals because the close resort store (your paying for convenience) is super pricey (10 for a carton of ice cream) .The massage chair will make you want to not leave at all anyways….If you want a delicious dinner out and don’t mind a little drive, the Mill street grill in staunton was great. Check the menu its a bit pricey but neat as it was a 19 century flour mill. Great ski house. Would love to return.

  • Dustin Z.

    Submitted Jan 11, 2025

    Stayed Dec 29, 2024

    This unit is as advertised and in a perfect location. Very clean with all the amenities you would need. The kids LOVED the message chair, big hit. Thanks for a wonderful getaway, we have already been asked to rebook!

  • Lisa K.

    Submitted Jan 7, 2025

    Stayed Dec 14, 2024

    Property had everything that we needed and more. Very comfortable beds! Would definitely stay again!

  • Sarah L.

    Submitted Jan 7, 2025

    Stayed Jan 4, 2025

    We booked a 2 night stay at Diamond Adventure at Wintergreen and were so happy that we did! The condo is one of the ones right off Diamond Hill ski slope and the high speed Blue Ridge Express 6 person lift goes right by the windows. It faces East and is just a lovely place. Beyond location, the condo itself is perfect for our family of 5 - mom, dad and 3 kids: 15 yo boy and 2 10 yo girls. We had plenty of room for sleeping and family dinner- it was fun to wave to the kids on the lift outside and convenient for one parent who doesn’t ski to feel “right there”. Host was great and we did have to reach out with a question about parking she was right on it. The condo has washer /dryer, a kitchen and a very well-placed mirror over the table so you could keep an eye on the football game no matter where you sat. But the hero is the massage chair- can’t say enough about the MASSAGE CHAIR!!! We were very comfortable and sad to leave, would rent again. It is actually ski in and ski out depending on the snow, your lift ticket already being loaded in your card, and whether slope right there is open and groomed- but we got lucky and it was! We drove our 10 yo beginner girls around to the lodge to get their lessons and let them enter the slopes by the main area which is much easier- (and 2 minutes drive) but my son and I both went into the slopes/resort off the parking lot which was awesome and probably once in a lifetime thing for us. Thank you!

  • Vinny and Megan V.

    Submitted Jan 5, 2025

    Stayed Dec 31, 2024

    Overall we had a great stay at Diamond Adventure at Wintergreen over New Year’s. Condo was in a convenient location, walkable to the resort and slopes. Kids had a blast with the games and everyone loved the massage chair. We are already thinking about next year!

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Total

Includes taxes and fees
$252+
View details