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Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Ski-in/ski-out condo near Wintergreen Resort

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

2 bedrooms, desk, travel crib, WiFi
Fridge, microwave, oven, stovetop
A row of modern multi-story buildings with balconies, a ski lift, and a snow-covered landscape.
A modern living room with a fireplace, a television mounted on a wooden wall, and a foosball table.
A room with a foosball table and a Christmas tree.

Reviews

10 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Air conditioning
  • Gym
  • Outdoor Space

Explore the area

View in a 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

Room options

About the area

Wintergreen

Near the slopes.Within half a mile (1 km) of this condo, you'll find Wintergreen Resort and George Washington National Forest. Reids Gap Trailhead is within 6 miles (10 km) and Raven's Roost Overlook is within 9 miles (15 km).
View more Condo rentals in WintergreenOpens in a new window

What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 km
  • Bold Rock Hard Cider Nellysford Cidery - 17 min drive - 19.1 km
  • Rockfish Gap Entrance Shenandoah - 28 min drive - 35.3 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

  • ‪Hill Top Berry Farm & Winery - ‬20 min drive
  • ‪Belties - ‬16 min drive
  • ‪The Edge - ‬10 min walk
  • ‪The Market - ‬11 min walk
  • ‪Devils Backbone Brewing Company - ‬12 min drive

About this property

Entire place

You'll have the entire condo to yourself and will only share it with other guests in your party.

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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  • Kitchen
  • Washer
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Property amenities

Ski

  • Close to skiing
  • Ski-in/ski-out access
  • Snowboarding nearby

Internet

  • Available in the condo: WiFi

Parking and transportation

  • Car recommended
  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided
  • Sofa bed

Bathroom

  • 2 bathrooms
  • Bathtub
  • Bathtub or shower
  • Hair dryer
  • Shower
  • Towels provided

Living spaces

  • Dining table
  • Fireplace

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Balcony

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Location highlights

  • In a village
  • In the mountains

Things to do

  • Arcade/game room
  • Foosball table
  • Golf
  • Gym
  • Ski-in/ski-out access
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Sledding nearby
  • Swimming nearby
  • Wildlife walks nearby
  • Winery tours nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Property located in a resort

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 24

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

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.

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Property Registration Number 1497

Property is also known as

orp5b58923x

Frequently asked questions

How close is Diamond Adventure at Wintergreen Resort *FULLY UPDATED* to the airport?

This condo is 41.3 mi (55-min drive) away from the Weyers Cave, VA (SHD-Shenandoah Valley Regional) airport, the closest popular airport to the property.

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

As of Jul 2, 2026, prices found for a 1-night stay for 2 adults at Diamond Adventure at Wintergreen Resort *FULLY UPDATED* on Jul 5, 2026 start from CA $231, excluding 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.

Does Diamond Adventure at Wintergreen Resort *FULLY UPDATED* have an airport shuttle?

Airport shuttle services are not available at this condo.

Does Diamond Adventure at Wintergreen Resort *FULLY UPDATED* offer free breakfast?

This condo does not offer free breakfast.

Is there a casino at Diamond Adventure at Wintergreen Resort *FULLY UPDATED*?

No, there is no casino at this condo.

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

Check-in begins at 4:00 PM.

Is there free parking at Diamond Adventure at Wintergreen Resort *FULLY UPDATED*?

Free parking is not available at this condo.

Does Diamond Adventure at Wintergreen Resort *FULLY UPDATED* have a pool?

This condo does not have a pool.

Does Diamond Adventure at Wintergreen Resort *FULLY UPDATED* have a spa?

There are no spa services available at this condo.

How close is Diamond Adventure at Wintergreen Resort *FULLY UPDATED* to downtown Wintergreen?

This condo is 3.3 mi away from Wintergreen.

Diamond Adventure at Wintergreen Resort *FULLY UPDATED* Reviews

Reviews

10

Exceptional

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

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

Joe A.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was as advertised. Great location.
Stayed 3 nights in Feb 2026
Verified

10/10 Excellent

Jennifer B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
This was a dream of a condo! Responsive host, beautiful vibe and view, and right on the slopes.
Stayed 2 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

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

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

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

Chris G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Outstanding location! Fabulous view, ski right in/out, newly renovated, very clean, the deluxe massage chair is amazing! We actually got snowed in and were scrambling to find overnight accommodations since there were new guests arriving and the owners were so helpful in assisting us. Thank you so much. We will DEFINITELY be back!!
Stayed 3 nights in Feb 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

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

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

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

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

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

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

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

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