Dragon's Back, 9BR 10BA in Wintergreen

Top rated by guests
Welcome to Dragon's Back, perched on the mountainside with glorious views
Gourmet kitchen
Kitchen, open to living room
Large kitchen island
Two full size refrigerators (side by side), 2 ovens, microwave
review stars
10Outstanding
(7 Ratings)
"A fabulous host: super responsive when we had questions and sent a comprehensive guide book ahead of time which helped us plan the trip."
Brooke S.
Don't miss out! Price and availability may change
10 / 10
Outstanding(7 Ratings)

Chalet in Massies Mill, VA

18 guests · 9 bedrooms · 10 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Great for petsBring all your friends and family, even the furry ones
Top-tier experienceA high end property in this area

About this chalet rental

Welcome to Dragon’s Back, one of Virginia's premier mountain chalets. With 6200 sq ft and some of the best views in the state, this 9 bedroom- each with it's own bathroom- was custom built for groups and sleeps 18 comfortably. You’ll love the oversized gourmet kitchen, grand octagonal dining room, decks with stunning views, game room, and gorgeous bathrooms. Also, pet friendly! Managed by Chris at New School Hosting.

There's a ton to do in the area! Dragon’s Back is about a mile to the slopes and a few minutes’ drive to all the dining and entertainment at Wintergreen. Some of the best hiking trails in the state are off the Blue Ridge Parkway (15 minutes from the home). Also nearby are two sandy-beach-entrance lakes plus a community pool for swimming, and over dozen wineries, breweries, and distilleries- all within a 30 minute drive.

The home layout is as follows:

Main level:
(Note: main entrance enters this level with zero steps from the flat driveway)

- Primary living room with sectional sofa, gas fireplace, extra table and chairs, and big screen TV
- Grand dining area for 20 with custom circular table serving as focal point of room. TV and fireplace also in this room.
- Large, fully stocked gourmet kitchen with 2 full size refrigerators, 2 dishwashers, 2 ovens, 6 burner gas stove, and island / bar seating for 8.
- BR 1: Primary bedroom with king bed, seating area, gas fireplace, and deck access. Ensuite bathroom features double vanities and oversized tile shower with side-by-side shower heads with individual controls
- Attached to BR 1 is an office with its own private half bath
- BR 2: Queen bedroom with ensuite bathroom
- BR 3: Two twin bedroom with ensuite bathroom
- Additional half bath near kitchen
- Laundry room
- Upper deck features multiple sitting areas, dining tables for 12 and 6, and a propane grill and fire table (propane provided for each)

Lower level:

- Additional living room / game room with 3 big screen TVs, kitchenette, shuffleboard table, 2 arcade machines, and table for 6 with lots of games
- BR 4: Queen bedroom with ensuite bathroom
- BR 5: King bedroom with ensuite bathroom
- BR 6: Queen bedroom with ensuite bathroom
- BR 7: King bedroom with ensuite bathroom
- BR 8: Queen bedroom with ensuite bathroom
- BR 9: 2 twin beds with full bathroom just across the hall (shared with common space)
- Lower deck features large octagonal screened in porch with seating and a few smaller dining tables

Other things to note:

- Dragon's Back is pet friendly! We allow up to 2 dogs with a $200 pet fee (total, not per dog or per night). Please do not let your dogs on the furniture, and remember to pick up after them outside :)
- We are open to hosting small weddings or other events, but only with advance notice before booking. Additional charges may apply, and we may decline certain requests. Do not book this property if you intend on having more than 18 people at the property at any time, without checking with us first.
- Wintergreen offers hiking, skiing, snowboarding, tubing, swimming, dining, spa, ropes course, golfing, and much more.
- The large flat driveway can easily fit 6-7 vehicles.
- Wifi is fast with a strong signal throughout the house and decks. Most bedrooms, plus both living rooms and the dining room, feature smart TVs where you can access all the main streaming services.
- We provide a fully stocked coffee bar with multiple coffee drip and Keurig options
- Linens and towels provided
- Guests can enjoy free community pool access in the summer season (though the HOA rules stipulate no more than 6 guests at a time, and the permitted hours are 2-6pm).
- Pack n play, high chair, and board games provided
- We do require a separate rental agreement, which we will send a link to e-sign after you book. There are no additional fees beyond those listed here.
- Please note that if you would like to send packages to the property, you do so at your own risk. USPS is particularly unreliable. We can not be held responsible for late or undelivered packages. Additionally, we charge $25 for any return services requested, in additional to actual postage.

Amenities at Dragon's Back, 9BR 10BA in Wintergreen

Non-smoking
Pets allowed
Family friendly

Map of Massies Mill, VA


Ratings and reviews

10 / 10
Outstanding(7 Ratings)
10 / 10Outstanding·Feb 2026
A fabulous host: super responsive when we had questions and sent a comprehensive guide book ahead of time which helped us plan the trip.
10 / 10Outstanding·Jan 2026
We enjoyed our stay at Dragon's Back for a long snowboarding weekend. The kitchen was well stocked to prepare meals for our group of 14 with teenagers and my work crew. We had minor issues but our host, David was quick to respond and helped us take care of the issue. The house was pet friendly, which was appreciated. We all were looking for a hot tub to sank in after our time on the mountain, that's was the only con of the house. The views are amazing and we will be back!
10 / 10Outstanding·Jan 2026
Beautiful mountain views. Comfortable, up to date bedrooms, and adjoining baths. Interesting dining room- would be great for retreats/ conferences. We had 60 degree weather, but unsure how one would navigate the steep, downhill road in snow/ ice.
10 / 10Outstanding·Jan 2026
This is a beautiful home and great location. The views are spectacular. The host David and was the best. Super responsive and helpful. Highly recommend it!

$$$$
vrbo logo

FAQs

Is parking included with this chalet?

Parking is not specified as an available amenity at Dragon's Back, 9BR 10BA in Wintergreen. For more information, we encourage you to contact the property about where to park.

Is there a pool at this chalet?

We didn’t find pool listed as an amenity for this chalet. It may be worth double checking if a pool is important for your stay.

Is Dragon's Back, 9BR 10BA in Wintergreen pet friendly?

Yes! This chalet is pet-friendly. For more information, we recommend contacting the booking provider about animal policies.

What amenities are available at Dragon's Back, 9BR 10BA in Wintergreen?

We found 3 amenities for this rental. This includes non-smoking, pets allowed, and family friendly.