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

No, pets are not allowed at this property.

Diamond Adventure at Wintergreen Resort *FULLY UPDATED* - Latest Reviews, Deals & Photos 2025

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

Offering ski-in/ski-out access, this condo building in Wintergreen is in the mountains, within a 5-minute walk of Wintergreen Resort and George Washington National Forest, and close to winter activities such as sledding. Reids Gap Trailhead and Sherando Lake Recreation Area are also within 9 mi (15 km).

10/10 Excellent

Meredith G.

Mar 4, 2025

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

Dave S.

Mar 20, 2025

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.

Jan 11, 2025

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

Mike-Anthony

Jun 17, 2023

Liked: Cleanliness, amenities, property conditions & facilities, communication

5 STARS will stay at again!!!!!

Stayed 3 nights in May 2023

10/10 Excellent

Allison Packer C.

Feb 4, 2025

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

Vinny and Megan V.

Jan 5, 2025

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

Kirsten T.

Jul 10, 2022

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.

Jan 28, 2024

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

Meredith M.

Jan 27, 2024

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

Derek A., Chapel Hill

Mar 11, 2023

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

Glen K.

Dec 31, 2023

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

Jan 5, 2024

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.

Jan 11, 2025

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

Lacie M.

Jan 18, 2023

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

Meredith M.

Feb 19, 2025

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

Stayed 3 nights in Jan 2025

10/10 Excellent

Holly B.

Feb 15, 2025

Stayed 4 nights in Jan 2025

10/10 Excellent

Lisa K.

Jan 7, 2025

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

Sarah L.

Jan 7, 2025

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

8/10 Good

Ricardo

May 14, 2024

Liked: Property conditions & facilities, communication

Stayed 3 nights in May 2024

10/10 Excellent

Michelle G., Camden

Feb 12, 2024

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

Matt H.

Dec 23, 2022

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.

Nov 6, 2022

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.

Oct 23, 2022

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

Oct 16, 2022

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

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Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

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