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Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Photo gallery for Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Snow and ski sports
Slope-side View
Living area
Living area
Osaki Encore Massage Chair

Reviews

10 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Ski-in/ski-out access
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Balcony

Explore the area

View map
Wintergreen Resort, VA
  • Place, Wintergreen Resort
    ‪1 min walk‬
  • Place, Bold Rock Hard Cider Nellysford Cidery
    ‪17 min drive‬
  • Place, University of Virginia
    ‪54 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪62 min drive‬

Rooms & beds

2 bedrooms (sleeps 8)

Living room

2 Double Sofa Beds

Primary Bedroom

1 King Bed

Secondary Bedroom

1 Single Bed and 1 Queen Bed

2 bathrooms

Guest Bath

Bathtub or shower · Bathtub · Toilet

Primary en suite

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Dining area

About this property

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

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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House Rules

Check in after 4:00 PM
Minimum age to rent: 24
Check out before 10:00 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
There is a rental agreement that must be signed within 48 hours of booking. The security deposit is also due within 48 hours of booking.
Smoking: No smoking or burning of any substance (including incense) is permitted inside the condo;
Pets: are not permitted at any time.

Important information

You need to know

Property Registration Number 1497
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

About the area

Wintergreen

Located in Wintergreen, this condo is in the mountains. Swannanoa Palace and Plumb House Museum are local landmarks, and the area's natural beauty can be seen at Shenandoah National Park and Rockfish Gap Entrance Shenandoah. Travelling with kids? Consider Wildlife Center of Virginia and War Fields. Enjoy the area's slopes with snowboarding and skiing, and don't miss out on the sledging.
Map
Wintergreen Resort, VA

What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 km
  • Bold Rock Hard Cider Nellysford Cidery - 17 min drive - 19.1 km
  • Blue Ridge Parkway North Entrance - 27 min drive - 34.3 km
  • University of Virginia - 54 min drive - 75.6 km
  • John Paul Jones Arena - 56 min drive - 75.9 km

Getting around

  • Staunton Station - 47 min drive
  • Weyers Cave, VA (SHD-Shenandoah Valley Regional) - 55 min drive

Restaurants

  • ‪Belties - ‬16 min drive
  • ‪Hill Top Berry Farm & Winery - ‬20 min drive
  • ‪Iron & Ale At Wintergreen Resort - ‬20 min drive
  • ‪The Edge - ‬10 min walk
  • ‪The Market - ‬11 min walk

Frequently asked questions

Is Diamond Adventure at Wintergreen Resort *FULLY UPDATED* pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Diamond Adventure at Wintergreen Resort *FULLY UPDATED*?

As of 6 May 2026, prices found for a 1-night stay for 2 adults at Diamond Adventure at Wintergreen Resort *FULLY UPDATED* on 7 Aug 2026 start from AU$253, 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.

How much is parking at Diamond Adventure at Wintergreen Resort *FULLY UPDATED*?

On-site parking is available at the property.

What time is check-in at Diamond Adventure at Wintergreen Resort *FULLY UPDATED*?

Check-in begins at 4:00 PM.

What time is check-out at Diamond Adventure at Wintergreen Resort *FULLY UPDATED*?

Checkout is at 10:00 AM.

Where is Diamond Adventure at Wintergreen Resort *FULLY UPDATED* located?

Offering ski-in/ski-out access, this condo building in Wintergreen is situated in the mountains, within 1 mile (2 km) of Wintergreen Resort and George Washington National Forest, and is convenient for winter activities, such as sledging. Reids Gap Trailhead and Sherando Lake Recreation Area 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. 36 out of 38 reviews
Rating 8 - Good. 2 out of 38 reviews
Rating 6 - Okay. 0 out of 38 reviews
Rating 4 - Poor. 0 out of 38 reviews
Rating 2 - Terrible. 0 out of 38 reviews

10/10

Cleanliness

10/10

Amenities

9.0/10

Property conditions & facilities

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Holly M.

We had an incredible stay this past week. The condo
Stayed 4 nights in Feb 2026
Verified

10/10 Excellent

Blayre G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Susan J.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Chris S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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!
Stayed 3 nights in Jan 2026
Verified

10/10 Excellent

Patrick E.

Liked: Cleanliness, check-in, communication, location, listing accuracy
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
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Susie P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The unit was in great condition and clean. Excellent views and ski in/ out was great to have.
Stayed 3 nights in Dec 2025
Verified

10/10 Excellent

Emily H.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Unit was well appointed with essentials and kitchen was well stocked!
Stayed 4 nights in Dec 2025
Verified

10/10 Excellent

Leslie L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Our stay was great! The highlight of our stay was the massage chair. We came to relax and that is pure relaxation. The space was beautiful and relaxing. The arcade game was a big hit with our kids. The only negatives about the place was that the coffee maker was clearly not cleaned, and had not been cleaned for some time as there were some mold present. Also, the trundle part of the bunk bed cannot be pulled out and used. Both of these things are not a huge deal (we cleaned the coffee maker and used it, and we just didn't use the trundle bed and had to make our kids sleep in the full bed because they were scared to stay on the top bunk...it was a bit rickety). None of these things are major enough to make me not want to stay here again. Those minor things do not outweigh the tons of positive things about the place. Such a great place for a weekend getaway!
Stayed 2 nights in Mar 2026
Verified

10/10 Excellent

Daniel W.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Great
Stayed 2 nights in Nov 2025
Verified

10/10 Excellent

Meredith G.

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

Perfect spot on the mountain with the best view

The location is very convenient with amazing views of the slopes and terrain park.
Stayed 3 nights in Feb 2025
Verified

10/10 Excellent

Mike-Anthony

Liked: Cleanliness, amenities, property conditions & facilities, communication
5 STARS will stay at again!!!!!
Stayed 3 nights in May 2023
Verified

10/10 Excellent

Lisa K.

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

Very cozy!!

Property had everything that we needed and more. Very comfortable beds! Would definitely stay again!
Stayed 3 nights in Dec 2024
Verified

10/10 Excellent

Dave S.

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

Ski in / Ski Out Massage Chair!!

The nicest places we’ve stayed. Ski in / ski out. Walkable to entire village. That massage chair was a dream
Stayed 3 nights in Mar 2025
Verified

10/10 Excellent

Dustin Z.

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

Amazing Stay

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!
Stayed 2 nights in Dec 2024
Verified

10/10 Excellent

Kirsten T.

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

Anniversary Get Away

Diamond Adventure was just as advertised. Well appointed and beautifully decorated!
Stayed 2 nights in Jul 2022
Verified

10/10 Excellent

Michelle G.

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

Excellent!!!

Great location and view. Very well stocked especially the kitchen. Owners truly thought of everything to make your stay comfortable.❤️
Stayed 4 nights in Feb 2024
Verified

10/10 Excellent

Derek A.

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

Great Location and Awesome amenities

Place was very clean, great location, easy parking, comfy beds, stocked kitchen, and foosball table and massage chair kept kiddos busy when we weren't skiing. The hallway locker was clutch as well. We'd definitely book this property again.
Stayed 4 nights in Feb 2023
Verified

8/10 Good

Tracey M.

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

Massage chair for the win!

Skiers loved the location and the massage chair. Great property. Def plan to return.
Stayed 1 night in Jan 2024
Verified

10/10 Excellent

Vinny and Megan V.

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

Fun Trip

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!
Stayed 4 nights in Dec 2024
Verified

10/10 Excellent

Meredith M.

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

Never disappoints!!!

This was our second time staying at Diamond Hill and we loved it just as much as the first! The condo has everything you need and the location can’t be beat. We loved being able to ski right out on the slopes and the views are simply stunning! We look forward to hopefully staying here again in the future!
Stayed 4 nights in Jan 2024
Verified

10/10 Excellent

Allison Packer C.

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

Very impressive!

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.
Stayed 3 nights in Jan 2025
Verified

10/10 Excellent

Glen K.

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

Comfortable with great views.

Great condo with high end finishes. We had 4 adults including my elderly mother and were very comfortable. Definitely room for more next time too. The massage chair was amazing and we had a good time with the games. Thanks for the great communication Phyllis. Can’t wait to stay again.
Stayed 3 nights in Dec 2023
Verified

10/10 Excellent

Treasure B.

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

Happy New Year's 2024!

What a great stay at this property. The location was amazing and if we would have had a little bit more snow, we would have been able to ski in/out. This unit has been updated and contains all the necessity items needed while staying on the mountain. We will definitely reach out to reserve this unit again.
Stayed 4 nights in Dec 2023
Verified

10/10 Excellent

Brittnay S.

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

Ski Report

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.
Stayed 4 nights in Jan 2025
Verified

10/10 Excellent

Lacie M.

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

Diamond is accurate; Best VRBO Ever

There is not enough space or time to tell you how great this property actually is. Being a ski in ski out is super important to me as a mom of three teenage boys. It was absolutely perfect for teenagers with the arcade, foosball table, and other fun games. All the sweet little extras made this stay wonderful; such as extra towels, coffee pods, hot chocolate packets, dish soap, and tide pods. The design of the condo was amazing and every inch maximized. The locking storage locker outside was amazing to keep all the snow and dirt OUT! Fireplace was cozy and the massage chair on point. The private porch off the master was cute! I loved being able to drink coffee on the back deck, curled up with a book, watching the terrain park. If you forced me to make one complaint, it would be there wasn’t a peep hole in the door to see out of. But, that’s me LOOKING for a complaint and being an overly cautious person. The beds were super comfortable and the weighted blankets for use in the living room were great! Will always seek this condo out when visiting WinterGreen in the future.
Stayed 2 nights in Jan 2023

About the host

Hosted by Phyllis Schiavone

Host profile image
Avid adventurer, Disney fanatic, die hard skier, scuba diver, and lover of spending magical moments with my husband and two children.

I live in Virginia, have family in the Disney vicinity and friends all over the world!

I look forward to connecting with you as your host and to making your stay as comfortable and enjoyable as possible. My cleaning service is top notch and makes sure to sanitize our home between guests for your safety.

Why they chose this property

We purchased our condo in Wintergreen because we love the community, skiing and how conveniently located it is within the Wintergreen community.

What makes this property unique

Mountain views that take your breath away, people watching as they ski and board down the slopes outside your window.

Languages:

English

Premier Host

They consistently provide great experiences for their guests
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