Chalet in Massies Mill, VA
8 guests · 3 bedrooms · 3 baths
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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 - 4 min drive
* Blackrock Park and trail – 3 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
Hikes with streams and waterfalls (easy to difficult) - short drive
- https://www.wtgpoa.org/all-trails
Current Events - Wintergreen Weekly Newsletter
* Operating hours of shops, restaurants, and activities at the resort
* https://www.wintergreenresort.com/the-wintergreen-weekly/
Pickleball / Tennis - Rodes Farm Center (in the Valley):
* Play tennis or pickleball at the community's first come, first served court at Rodes Farm Center. Certain blocks of time are scheduled for tennis or pickleball. Please review the rules here:
* https://www.wtgpoa.org/rodes-farm-tennis-pickleball-fall-2023
* 1070 Rodes Farm Dr, Nellysford, VA 22958
Swimming Pools (2)
Up to six (6) guests must be pre-registered in order to use either of the outdoor community pools. Guest hours are 2-6 PM, Memorial Day to Labor Day. Please contact if your party is planning to swim. Community pools have locations have parking on site. Primary registered guest must bring photo ID.
* Rodes Farm Center (in the Valley)
** 1070 Rodes Farm Dr, Nellysford, VA 22958
** https://www.wtgpoa.org/rodes-farm
* Chestnut Springs Park (up the Mountain)
** 94 Timber Camp Dr, Wintergreen Resort, VA 22967
** https://www.wtgpoa.org/chestnut-springs
Nearby Trails (at the Mountain):
* The Plunge at Blackrock Park (3 min drive):
** https://www.alltrails.com/explore/trail/us/virginia/the-plunge
* Three Ridges Overlook + The Plunge (3 min drive):
** https://www.alltrails.com/explore/trail/us/virginia/three-ridges-overlook-to-the-plunge-via-the-brimstone-trail
* Laurel Ridge Loop (5 min drive):
** https://www.alltrails.com/explore/trail/us/virginia/laurel-ridge-loop-trail
* Cedar Cliffs North and Main Trail Loop (7 min drive)
** https://www.alltrails.com/explore/trail/us/virginia/cedar-cliffs-north-and-main-trail-loop
* Hemlock Springs and Cedar Cliffs Trail Loop (7 min drive)
** https://www.alltrails.com/explore/trail/us/virginia/hemlock-springs-and-cedar-cliffs-trail-loop
* Old Appalachian Trail Out-and-Back from Hemlock Drive
** https://www.alltrails.com/explore/trail/us/virginia/old-appalachian-trail-out-and-back-from-hemlock-drive
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 - 4 min drive
* Blackrock Park and trail – 3 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
Hikes with streams and waterfalls (easy to difficult) - short drive
- https://www.wtgpoa.org/all-trails
Current Events - Wintergreen Weekly Newsletter
* Operating hours of shops, restaurants, and activities at the resort
* https://www.wintergreenresort.com/the-wintergreen-weekly/
Pickleball / Tennis - Rodes Farm Center (in the Valley):
* Play tennis or pickleball at the community's first come, first served court at Rodes Farm Center. Certain blocks of time are scheduled for tennis or pickleball. Please review the rules here:
* https://www.wtgpoa.org/rodes-farm-tennis-pickleball-fall-2023
* 1070 Rodes Farm Dr, Nellysford, VA 22958
Swimming Pools (2)
Up to six (6) guests must be pre-registered in order to use either of the outdoor community pools. Guest hours are 2-6 PM, Memorial Day to Labor Day. Please contact if your party is planning to swim. Community pools have locations have parking on site. Primary registered guest must bring photo ID.
* Rodes Farm Center (in the Valley)
** 1070 Rodes Farm Dr, Nellysford, VA 22958
** https://www.wtgpoa.org/rodes-farm
* Chestnut Springs Park (up the Mountain)
** 94 Timber Camp Dr, Wintergreen Resort, VA 22967
** https://www.wtgpoa.org/chestnut-springs
Nearby Trails (at the Mountain):
* The Plunge at Blackrock Park (3 min drive):
** https://www.alltrails.com/explore/trail/us/virginia/the-plunge
* Three Ridges Overlook + The Plunge (3 min drive):
** https://www.alltrails.com/explore/trail/us/virginia/three-ridges-overlook-to-the-plunge-via-the-brimstone-trail
* Laurel Ridge Loop (5 min drive):
** https://www.alltrails.com/explore/trail/us/virginia/laurel-ridge-loop-trail
* Cedar Cliffs North and Main Trail Loop (7 min drive)
** https://www.alltrails.com/explore/trail/us/virginia/cedar-cliffs-north-and-main-trail-loop
* Hemlock Springs and Cedar Cliffs Trail Loop (7 min drive)
** https://www.alltrails.com/explore/trail/us/virginia/hemlock-springs-and-cedar-cliffs-trail-loop
* Old Appalachian Trail Out-and-Back from Hemlock Drive
** https://www.alltrails.com/explore/trail/us/virginia/old-appalachian-trail-out-and-back-from-hemlock-drive
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
We loved our time here. Great location for ski in/out and the amenities are excellent. Host was easily accessible and would love to stay here again.
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.
$$$$
Top rated by guests
10Outstanding
(8 Ratings)
"We loved our time here. Great location for ski in/out and the amenities are excellent. Host was easily accessible and would love to stay here again. "
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