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Entire condo

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Family-friendly slopeside fun near snowboarding

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

Fridge, microwave, oven, stovetop - Diamond Adventure at Wintergreen Resort *FULLY UPDATED* (Wintergreen Resort)
Interior - Diamond Adventure at Wintergreen Resort *FULLY UPDATED* (Wintergreen Resort)
Interior - Diamond Adventure at Wintergreen Resort *FULLY UPDATED* (Wintergreen Resort)
Exterior - Diamond Adventure at Wintergreen Resort *FULLY UPDATED* (Wintergreen Resort)
Terrace/patio - Diamond Adventure at Wintergreen Resort *FULLY UPDATED* (Wintergreen Resort)
High atop Upper Diamond Hill, Wintergreen condo offers a haven with mountain views and slope-side convenience. Take in the morning sunrise from your private balcony or sip wine as the day winds down, surrounded by amazing colors. Enjoy ski-in/ski-out access during winter months or hiking adventures year-round.

Reviews

10 out of 10
Exceptional

Entire condo

2 bedrooms2 bathroomsSleeps 8

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Air-conditioning
  • Gym
  • Outdoor space
The current price is AU$721
includes taxes & fees
20 Jan - 21 Jan

Add dates for prices

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.

Property amenities

Ski

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

Internet

  • Available in the condo: WiFi

Parking and transport

  • Car recommended
  • Parking on site

Kitchen

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

  • Smoke-free property

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

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Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are 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

Pets not 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
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
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
Property Registration Number 1497

We should mention

A car is recommended for transport to and from this property

Property is also known as

orp5b58923x

About the area

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.
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Map
Wintergreen Resort, VA

What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 km
  • Bold Rock Hard Cider Nellysford Cidery - 12 min drive - 15.3 km
  • Shenandoah National Park - 19 min drive - 23.1 km
  • University of Virginia - 38 min drive - 61.9 km
  • Monticello - 45 min drive - 70.2 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
  • ‪Devils Backbone Brewing Company - ‬13 min drive
  • ‪Iron & Ale At Wintergreen Resort - ‬20 min drive
  • ‪Trager Bros Coffee Shop - ‬21 min drive

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 17 Jan 2026, prices found for a 1-night stay for 2 adults at Diamond Adventure at Wintergreen Resort *FULLY UPDATED* on 20 Jan 2026 start from AU$721.20, 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 a 5-minute walk 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).

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Diamond Adventure at Wintergreen Resort *FULLY UPDATED* Reviews

Reviews

Exceptional

All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative.
More informationOpens in a new window
Rating 10 - Excellent. 27 out of 29 reviews
Rating 8 - Good. 2 out of 29 reviews
Rating 6 - Okay. 0 out of 29 reviews
Rating 4 - Poor. 0 out of 29 reviews
Rating 2 - Terrible. 0 out of 29 reviews

10

Cleanliness

10

Location

9.0

Property conditions & facilities

Reviews

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

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

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

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

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

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

10/10 Excellent

Michelle G., Camden

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

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

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

10/10 Excellent

Treasure B., Raleigh, NC

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

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

10/10 Excellent

Sarah L.

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

A Special Place!

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!
Stayed 2 nights in Jan 2025

10/10 Excellent

Mike-Anthony

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

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

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

10/10 Excellent

Derek A., Chapel Hill

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

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

10/10 Excellent

Matt H.

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

Great location

What a fabulous place. Great view, great location and great host. Right on the slopes and wonderfully outfitted
Stayed 3 nights in Dec 2022

10/10 Excellent

Chris H.

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

Nice place

The condo was very clean, cute and modern. We will definitely be staying here again in the future.
Stayed 2 nights in Nov 2022

10/10 Excellent

Ann K.

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

Great stay in Wintergreen.

Owner communication was great. Awesome sunrise. Very clean. Comfortable bed. Overall great stay.
Stayed 2 nights in Oct 2022

10/10 Excellent

Cathy M., Chapel Hill, NC

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

Beautiful and comfortable condo

We had a wonderful stay at Diamond Adventure Condo. The unit has recently been completely remodeled so everything was brand new and very clean. The bed was very comfy and the kitchen was well stocked. The unit was well appointed with very comfortable furnishings that made us feel right at home. The morning sunrises were stunning directly out the front windows of the unit. It is centrally located within Wintergreen for easy access to everything and is just a short walk to the ski lodge and shops. During our stay we enjoyed apple picking in Tyro, many beautiful hikes including part of the AT and visited many of the local breweries, cideries and wineries. We will definitely stay at this condo again in the future.
Stayed 4 nights in Oct 2022

10/10 Excellent

Meredith M.

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

10/10 Excellent

Holly B.

Stayed 4 nights in Jan 2025

8/10 Good

Ricardo

Liked: Property conditions & facilities, communication
Stayed 3 nights in May 2024