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Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Family-friendly slopeside fun near snowboarding

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

Fridge, microwave, oven, stovetop
Exterior
Interior
Terrace/patio
Interior

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
    ‪12 min drive‬
  • Place, Shenandoah National Park
    ‪19 min drive‬
  • Airport, Weyers Cave, VA (SHD-Shenandoah Valley Regional)
    ‪50 min drive‬

Room options

About the neighborhood

Wintergreen

This condo places you next to Wintergreen Resort and George Washington National Forest. The condo includes a kitchen, a fireplace, and a balcony.
View more Condo Rentals in WintergreenOpens in a new window

What's nearby

  • Wintergreen Resort - 1 min walk - 0.0 miles
  • Bold Rock Hard Cider Nellysford Cidery - 12 min drive - 9.6 miles
  • Shenandoah National Park - 19 min drive - 14.4 miles
  • University of Virginia - 38 min drive - 38.5 miles
  • Monticello - 45 min drive - 43.6 miles

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

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.
The condo is air-conditioned and features a kitchen, 2 bathrooms, and a balcony, and there's space to spread out with 2 bedrooms. Other standard amenities include a washing machine, a fireplace, and a sofa bed.

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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

  • This property doesn't allow pets

Children and extra beds

Children allowed: ages 0-17

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
  • Check-in: 4:00 PM
  • Check-out: 10:00 AM
  • Minimum check-in age: 24
Property Registration Number 1497

We should mention

Details about charges, deposits, or other important information:

  • This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
  • Charges for extra guests may apply and vary depending on the property's policy.
  • A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
  • Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
  • Onsite parties or group events are strictly prohibited.
  • Onsite safety features include a carbon monoxide detector, a fire extinguisher, and a smoke detector.

Property is also known as

orp5b58923x

Frequently asked questions

What's there to do close to this condo?

This condo is located in Wintergreen and just steps from Wintergreen Resort and George Washington National Forest. Reids Gap Trailhead is also within a driving distance of 3.8 mi.

Is there parking available at this condo?

No, there isn't parking available at the condo.

Is this condo adjacent to a casino?

No, this condo is not connected to a casino.

Is there an indoor pool at this condo?

No, there is no indoor pool at this condo.

What do couples enjoy most about Diamond Adventure at Wintergreen Resort *FULLY UPDATED*?

There are many amenities for couples at this condo, including a fireplace, fireplaces in some condo units, as well as ski-in/out access.

Are there hot tubs at Diamond Adventure at Wintergreen Resort *FULLY UPDATED*?

No, this condo doesn't have a spa tub.

Does this condo offer breakfast?

No, this condo doesn't offer breakfast.

Does this condo allow pets to stay for free?

No, pets aren't allowed at this condo.

Does this condo have connecting rooms?

No, this condo doesn't feature connecting guestrooms.

How close is the airport from this condo?

The closest major airport to this condo is Weyers Cave, VA (SHD-Shenandoah Valley Regional), which is about 24.1 mi away.

Can I book a room with a balcony at Diamond Adventure at Wintergreen Resort *FULLY UPDATED*?

Yes, every condo unit at Diamond Adventure at Wintergreen Resort *FULLY UPDATED* comes with a balcony with some featuring mountain views.

Diamond Adventure at Wintergreen Resort *FULLY UPDATED* Reviews

Reviews

10

Exceptional

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

10/10

Cleanliness

10/10

Amenities

9.0/10

Property conditions & facilities

Reviews

10/10 Excellent

Susan J.

Liked: Cleanliness
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

10/10 Excellent

Susie P.

Liked: Cleanliness
The unit was in great condition and clean. Excellent views and ski in/ out was great to have.
Stayed 3 nights in Dec 2025

10/10 Excellent

Patrick E.

Liked: Cleanliness
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

10/10 Excellent

Emily H.

Liked: Cleanliness
Unit was well appointed with essentials and kitchen was well stocked!
Stayed 4 nights in Dec 2025

10/10 Excellent

Daniel W.

Liked: Cleanliness
Great
Stayed 2 nights in Nov 2025

10/10 Excellent

Dave S.

Liked: Cleanliness

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

Meredith G.

Liked: Cleanliness

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

Meredith M.

Liked: Cleanliness
Stayed 3 nights in Jan 2025

10/10 Excellent

Holly B.

Stayed 4 nights in Jan 2025

10/10 Excellent

Allison Packer C.

Liked: Cleanliness

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

Brittnay S., Nc

Liked: Cleanliness

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

Dustin Z.

Liked: Cleanliness

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

Lisa K.

Liked: Cleanliness

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

Sarah L.

Liked: Cleanliness

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

Vinny and Megan V.

Liked: Cleanliness

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

8/10 Good

Ricardo

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

10/10 Excellent

Michelle G., Camden

Liked: Cleanliness

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

8/10 Good

Tracey M.

Liked: Cleanliness

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

Meredith M.

Liked: Cleanliness

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

Treasure B., Raleigh, NC

Liked: Cleanliness

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

Glen K.

Liked: Cleanliness

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

Mike-Anthony

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

10/10 Excellent

Derek A., Chapel Hill

Liked: Cleanliness

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

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

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