Chalet in Massies Mill, VA
8 guests · 3 bedrooms · 3 baths
Reasons to book
Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
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About this chalet rental
Alpine Ascent – Luxury Ski-In/Ski-Out Chalet with Mountain Views at Wintergreen Resort
Welcome to Alpine Ascent, where luxury meets adventure at this fully renovated 3BR/3BA slope-side chalet perched directly on the Tyro ski slope at Wintergreen Resort. Alpine Ascent blends modern comfort, refined style, and true ski-in/ski-out convenience with beautiful mountain scenery. Glide out for first tracks in the morning or sip wine by the fire pit as skiers pass by at dusk.
Inside, contemporary design meets alpine charm. Warm wood textures, plush furnishings, and curated décor create a cozy yet upscale vibe perfect for relaxing after a day on the slopes or after exploring the beauty of the Blue Ridge Mountains in any season. In spring and summer, guests can head out for numerous scenic hikes for all levels, sample award winning wineries and cideries, or play a round of golf under bright mountain skies. When autumn arrives, the chalet becomes a front-row seat to the region’s fiery foliage, with gorgeous mountain views that wrap the home in color.
This cozy, stylish cottage truly has it all for year-round enjoyment — a place where comfort, adventure, and the best of Wintergreen come together effortlessly.
The Space - Sleeps 6 guests privately (up to 8 guests total):
* Bedroom 1: King bed, private ensuite bathroom with beautifully tiled shower
* Bedroom 2: Queen bed, adjacent to a full bathroom with shower
* Bedroom 3 (Upper Level – Closed Loft): Queen bed, attached bathroom with shower
* Living Room: Queen sofa bed
The open living area flows into an upscale kitchen and spacious dining space, ideal for entertaining or enjoying family meals. Step outside onto the private deck for panoramic mountain views, or unwind around the outdoor fire pit as snowflakes fall.
Highlights & Amenities:
* True Ski-In/Ski-Out Access to Tyro Slope — no shuttles, just step out to the path and go
* Fully Renovated — floor-to-ceiling modern finishes
* Mudroom with ski gear storage
* Upscale kitchen with Keurig (pods + drip), premium-quality cookware, utensils, accessories, and dining set--this is one of the best stocked kitchens in the resort!
* Smart TV and free high-speed WiFi
* Google Speaker and Nest Hub to listen to your favorite music
* Fire Pit & Deck with Mountain View’s
* Washer & Dryer
* Central Air Conditioning & Heating
* Two Onsite Parking Spaces (four steps down from lot to main level entry)
* Safety Essentials: Smoke & carbon monoxide detectors, fire extinguisher, fire blankets
Hypoallergenic Friendly:
- Pet-Free & Smoke-Free Property
- Hardwood floors, tile floors
- High MERV allergen filters
Nearby Attractions:
* Ski-out/Ski-in access to Tyro slope at the home
* Scenic Overlook (Blackrock Dr) - 1 min drive
* The Market at Wintergreen – 2 min drive
* Shops and restaurants at Wintergreen Resort - 2 min drive
* Blackrock Park – 2 min drive
* Founder's Vision Overlook (Wintergreen Dr) - 5 min drive
* Raven’s Roost Overlook (Blue Ridge Parkway) – 10 min drive
* Bold Rock Nellysford Cidery – 15 min drive
* University of Virginia, Charlottesville – 45 min drive
* Carter Mountain Orchard – 55 min drive
* Numerous hikes with streams and waterfalls (easy to difficult) - short drive
- https://www.wtgpoa.org/all-trails
* See the Wintergreen Weekly newsletter for operating hours of shops, restaurants, and activities at the resort
- https://www.wintergreenresort.com/the-wintergreen-weekly/
Welcome to Alpine Ascent, where luxury meets adventure at this fully renovated 3BR/3BA slope-side chalet perched directly on the Tyro ski slope at Wintergreen Resort. Alpine Ascent blends modern comfort, refined style, and true ski-in/ski-out convenience with beautiful mountain scenery. Glide out for first tracks in the morning or sip wine by the fire pit as skiers pass by at dusk.
Inside, contemporary design meets alpine charm. Warm wood textures, plush furnishings, and curated décor create a cozy yet upscale vibe perfect for relaxing after a day on the slopes or after exploring the beauty of the Blue Ridge Mountains in any season. In spring and summer, guests can head out for numerous scenic hikes for all levels, sample award winning wineries and cideries, or play a round of golf under bright mountain skies. When autumn arrives, the chalet becomes a front-row seat to the region’s fiery foliage, with gorgeous mountain views that wrap the home in color.
This cozy, stylish cottage truly has it all for year-round enjoyment — a place where comfort, adventure, and the best of Wintergreen come together effortlessly.
The Space - Sleeps 6 guests privately (up to 8 guests total):
* Bedroom 1: King bed, private ensuite bathroom with beautifully tiled shower
* Bedroom 2: Queen bed, adjacent to a full bathroom with shower
* Bedroom 3 (Upper Level – Closed Loft): Queen bed, attached bathroom with shower
* Living Room: Queen sofa bed
The open living area flows into an upscale kitchen and spacious dining space, ideal for entertaining or enjoying family meals. Step outside onto the private deck for panoramic mountain views, or unwind around the outdoor fire pit as snowflakes fall.
Highlights & Amenities:
* True Ski-In/Ski-Out Access to Tyro Slope — no shuttles, just step out to the path and go
* Fully Renovated — floor-to-ceiling modern finishes
* Mudroom with ski gear storage
* Upscale kitchen with Keurig (pods + drip), premium-quality cookware, utensils, accessories, and dining set--this is one of the best stocked kitchens in the resort!
* Smart TV and free high-speed WiFi
* Google Speaker and Nest Hub to listen to your favorite music
* Fire Pit & Deck with Mountain View’s
* Washer & Dryer
* Central Air Conditioning & Heating
* Two Onsite Parking Spaces (four steps down from lot to main level entry)
* Safety Essentials: Smoke & carbon monoxide detectors, fire extinguisher, fire blankets
Hypoallergenic Friendly:
- Pet-Free & Smoke-Free Property
- Hardwood floors, tile floors
- High MERV allergen filters
Nearby Attractions:
* Ski-out/Ski-in access to Tyro slope at the home
* Scenic Overlook (Blackrock Dr) - 1 min drive
* The Market at Wintergreen – 2 min drive
* Shops and restaurants at Wintergreen Resort - 2 min drive
* Blackrock Park – 2 min drive
* Founder's Vision Overlook (Wintergreen Dr) - 5 min drive
* Raven’s Roost Overlook (Blue Ridge Parkway) – 10 min drive
* Bold Rock Nellysford Cidery – 15 min drive
* University of Virginia, Charlottesville – 45 min drive
* Carter Mountain Orchard – 55 min drive
* Numerous hikes with streams and waterfalls (easy to difficult) - short drive
- https://www.wtgpoa.org/all-trails
* See the Wintergreen Weekly newsletter for operating hours of shops, restaurants, and activities at the resort
- https://www.wintergreenresort.com/the-wintergreen-weekly/
Amenities at Luxury Ski-in/Ski-out Chalet with Mountain Views at Wintergreen Resort
Non-smoking
No pets allowed
Family friendly
Map of Massies Mill, VA
Ratings and reviews
10 / 10Outstanding·Feb 2026
This was the first time we had ever traveled and had ALL of the things needed at our fingertips without having to bring them from home. Our host was rather efficient in response time and most helpful with any of our needs.
10 / 10Outstanding·Feb 2026
Beautiful unit and an incredible location right on the slope. So easy to ski in/ski out! Check-in and check-out were also very smooth, and we appreciated the communication from the hosts leading up to our stay. It was also great to have the house already stocked with coffee and some other essentials. We would definitely stay again!
10 / 10Outstanding·Feb 2026
The Hosts did a great job of communicating and the house was very clean.
10 / 10Outstanding·Jan 2026
The house was awesome! Loved the location, decor and everything about it. Owners communicated with us very well and we loved everything about it. Will definitely rent this house again!
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Top rated by guests
10Outstanding
(8 Ratings)
"This was the first time we had ever traveled and had ALL of the things needed at our fingertips without having to bring them from home. Our host was rather efficient in response time and most helpful..."
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