9 Best Chalets in Wintergreen Resort, VA

Shangri-la! A Perfect Getaway for everyone! is a recently renovated chalet in Beech Grove where guests can make the most of the garden and shared lounge. This property offers access to a patio, free private parking, and free Wifi. Outdoor dining is also possible at the chalet. The air-conditioned chalet also provides a flat-screen TV, a fully equipped kitchen with a dishwasher, a seating area, washing machine, and 3 bathrooms with a walk-in shower. The accommodation has a fireplace. The nearest airport is Shenandoah Valley Regional Airport, 42 miles from Shangri-la! A Perfect Getaway for everyone!.

Internet • Child Friendly • Kitchen • Air Conditioner • Tv • Parking • Other

Enjoy this charming 3-bedroom, 2-bathroom house located on the slopes of Tyro. Step outside, strap on your boards or skis, and hit the slopes!

We provide all essential amenities, including linens for the bedrooms and bathrooms, soaps, K-cup coffee, creamers, towels, and full kitchen supplies. Stay connected with complimentary Wi-Fi and smart TVs. You'll also find snacks, hot chocolate, green tea, popcorn, a complimentary bottle of wine, firewood, and a firewood starter available for your convenience.

This location is perfect for winter skiing and spring and summer hiking. It is also conveniently close to great breweries and wineries. Enjoy a peaceful atmosphere with breathtaking sunrise views over the mountains.

- "Great property, very comfortable. We enjoyed the location and convenience to the slopes... even with Lower Tyro closed. Everything you could want for a mountain stay! The home is very nice and the owners are prompt to respond. Planning a return visit!" - "Our family ski weekend got canceled due to Wintergreen ending their season due to warm weather, but thankfully we were still able to enjoy our time in a beautiful home. The sunrises from Treeloft are breathtaking. So many "extras" such as additional toiletries, snacks, coffee, etc. were provided. We had our grandchildren with us, and they took advantage of some of the games and puzzles. There was plenty of firewood and we enjoyed cozy fires. Ironically, our first full day we spent there we were under a winter weather advisory. It rained, sleeted and was foggy ALL day. Because we were in such an idyllic setting, we were able to spend a perfect day with family and enjoyed watching the wintry mix from the comfort of indoors. The fog was so thick, we couldn't even see the slope outside our window. The grandkids said it was like we were perched in the clouds. All of those "extras" sure came in handy! Check-in was easy and convenient. Communication response with the owner, Jimmy, was immediate. The beds were extremely comfortable...much more so than I would expect. The grandkids loved the spiral staircase and the loft bedroom. Treeloft is an ideal place to enjoy time with family...we hope to be back again!"

Gorgeous Blue Ridge Mountain Weekend Escape!
Well mannered Pets welcomed with owners permission. Must ask ahead. We welcome you to our gorgeous mountain escape!! For discriminating guests who seek the finest accommodations and our property is one of the only large ski in ski out home for rent at Wintergreen Resort. Superb for a family ski vacation, beautiful for a summer get away to beat the heat, or a sneak away to see the beautiful autumn colors.

There are beautiful views of the mountains from every room. The spacious main deck allows watching the skiers race down the mountain in the winter, or relaxing and dining at tree top level. Our great room includes a cathedral ceiling and cedar post construction, as well as a dramatic floor to ceiling stone fireplace. Decorated with comfortable but elegant furnishings and tasteful accessories.

The three upstairs bedrooms are spacious with lots of windows. Romantic king-size master suite on the main floor. Two small guest rooms on the lower level. Four and half baths, pillow-top mattresses, down comforters and pillows in all bedrooms.

Lower Level includes large screen TV, DVD , plus game room with ping pong table, hockey table, and dart board, with access to the lower deck.

Our home is located a few minutes drive to the Mountain Inn, Tennis Center, Wintergreen Spa, the Nature Foundation and the famous Devils Golf Course. The 27 hole Stoney Creek Golf Course, Clubhouse, Lake Monocan and more tennis courts are just 20 minutes down the mountain in the valley section of Wintergreen. There are also numerous restaurants, breweries, wineries and hard cider places near by. It is a terrific location.

9 guests maximum

- "The property was beautiful and fit our family well. The open floor plan was important to me so that the family could be together for everything. We would have liked for the hot tub to be working but it want that big a deal. The Smeallie’s were very communicative and kind. I would recommend this location and the Smeallie’s to family and friends." - "The house is beautiful! The owners go above and beyond to make sure you have everything you need. The location is perfect!!! We can’t wait to come back."

This secluded Chalet has minimal stairs, most rooms and deck on same level. Ideal work-from-home alternative for staycation or weekend get-away for families. This cozy home features high vaulted ceilings, 3 large bedrooms, 2 full bathrooms and a huge deck that wraps around the entire back of the home with terrific mountain views through the treetops. Located just 150 yds from top of 3 slopes, easy public access w/o need to shuttle.

- "We loved our stay! It was an excellent location and close to a lift for 2 blue and 2 black runs. Everything was clean and comfortable. My family had an excellent time and we would be thrilled to stay here again!" - "Everything was great! Plenty of room for 2 adults and 3 teenage boys. This was probably the best stocked house we have booked through VRBO. We appreciated how much thought the owner put into making it feel like home." - "Enjoyed getting out of the city for some peace and quiet."

Welcome to The Moose Lodge at Wintergreen – Your Mountain Escape Awaits!

Gather your family and friends and make unforgettable memories in this beautiful 4-bedroom chalet located in the heart of Wintergreen Resort. Comfortably sleeps 12 adult guests with a pull out sofa and loft daybed trundle for the kids, The Moose Lodge is your perfect year-round getaway for skiing, hiking, leaf-peeping, or simply relaxing in nature.

Inside, you'll find a spacious and inviting layout featuring:

Fully equipped/stocked kitchen with gas stove, ice maker and beverage cooler!
A cozy living room with large windows, vaulted ceilings, and a pull-out sofa bed for extra space.

Four Bedrooms (one is a loft) and 3 full bathrooms-don't worry about brining your hair dryer!

Washer/Dryer, Iron and Ironing Board, and Central Heating & AC

Fast WiFi throughout the home to stay connected (if you want to!). Game Room has a dedicated work space.

Whether you’re soaking in the hot tub after a day on the slopes, enjoying the fire pit under the stars, playing games in the game room (Pool table, Ping Pong, Air Hockey and board games provided), or grilling dinner on the deck (Propane Grill), The Moose Lodge offers everything you need to feel right at home.

We're located just 0.7 miles from the ski lodge, making it easy to hit the slopes, grab a bite, or explore all that Wintergreen Resort has to offer.

We can’t wait to host you — come experience mountain comfort at its finest at The Moose Lodge!

Tv • Fireplace/Heating • Hot Tub • Balcony/Terrace • Security/Safety • Kitchen • Child Friendly • Other • Laundry • Sports/Activities • Barbecue/Outdoor Cooking • Bedding/Linens

Wintergreen Ridge Retreat: Cozy Mountain Getaway

Welcome to Wintergreen Ridge Retreat, your perfect escape at Wintergreen Resort, VA! Just 3 minutes from the ski slopes and snow tubing, our spacious and comfortable home offers a seamless blend of
four seasons adventure. Whether you're carving down the slopes, exploring over 30 miles of hiking trails, or simply unwinding in the peaceful surroundings, this retreat has it all.

The space
Bedrooms:
The retreat comfortably accommodates up to 10 guests across 3 well-appointed bedrooms and loft bedroom. The main level features 2 cozy bedrooms for easy access (Bedroom 2 King and Bedroom 3 two Queen Beds). While the upper level offers a private sanctuary the primary bedroom with attached bathroom (Bedroom 1 King). Loft is upstairs with twin bunk bed.

Bathrooms:
With 2 full bathrooms and a convenient half-bath on the main level, plus another full bathroom upstairs, there's plenty of space for everyone to refresh and relax after a day of exploration.

Amenities:
Outdoor Adventures:
Take advantage of two community pools, perfect for a summer swim. (Chestnut Springs on the mountain
and Rodes Farm in the valley). In the winter skiing, snowboarding, or snow tubing just minutes away. Indoor adventure park for family fun!

Local Attractions:
Indulge in local dining with seven options just a short drive away. Explore nearby wineries and breweries for a taste of the region, or immerse yourself in nature with countless hiking trails right at your doorstep.

Why You'll Love Wintergreen Ridge Retreat:

This home is your gateway to both excitement and relaxation, making it the ideal base for your Wintergreen adventures. Whether you're seeking thrills on the slopes or a peaceful retreat in the mountains, Wintergreen Ridge Retreat offers everything you need for an unforgettable stay.

We are pet friendly! **Please let us know if you have a pet. We have a one time Pet Fee: $130.** No more than 2 dogs.


Book your stay at Wintergreen Ridge Retreat today and discover the best of Wintergreen Resort!

Guest access
Guest has full access on our property.

Other things to note
WINTERGREEN ACTIVITIES: Wintergreen Ski Resort, Discovery Ridge Adventure Center, Wintergreen Adaptive Sports, Shamokin Springs Nature Preserve, The Plunge Snow Tubing Park, Stony Creek Golf Course, on-site dining, walking trails, panoramic viewing platform

ATTRACTIONS: Appalachian Trail Head (8.9 miles), Blue Ridge Parkway (5.0 miles), Three Ridges Overlook (5.5 miles), Shenandoah National Park (19.2 miles), Appomattox Court House National Historical Park (57.8 miles)

WINE and BEER: Devil's Backbone Basecamp Brewpub (8.7 miles), Hill Top Berry Farm and Winery (14.1 miles), Wood Ridge Farm Brewery (20.7 miles), Seven Arrows Brewing Company (20.8 miles), Blue Mountain Brewery (21.6 miles), Veritas Vineyards and Winery (22.3 miles), Afton Mountain Vineyards (22.6 miles) HIKING: Highlands Leisure Trail (1.7 miles), Upper Shamokin Falls Trail (1.8 miles), Appalachian Trail-Three Ridges Hike (5.0 miles), Crabtree Falls (20.7 miles)

AIRPORT: Charlottesville Albemarle Airport (49.2 miles)
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WATER ACTIVITIES: While the resort’s pools are reserved for members only, this property has access to the HOA pools at Chestnut Springs on the mountain (94 Timber Camp Dr) and Rodes Farm in the valley (Stoney Creek). These pools operate from the Saturday of Memorial Day Weekend through Labor Day. Unaccompanied guests of property owners may use the pools from 2 pm until 6 pm daily. With a guest pass, six guests can access the pool. The limit on people using WPOA pools per property is six. In addition to the pools, there are two fresh water lakes with swimming nearby. Lake Monocan, a 20-acre lake and park operated by the resort that is located at 239 Camping Ridge Lane in Stoney Creek. There is a fee per person to enter and it is closed to the public on Saturdays. Sherando Lake Recreation Area is also nearby. Known locally as the jewel of the Blue Ridge Mountains. Families enjoy picnicking in this shaded and woody area, while relaxing on the sandy beach of a 25-acre spring-fed lake. Access to multiple trailheads and rustic architecture provide numerous points of interest for families to enjoy. $8 per vehicle up to 8 passenger capacity for day use.

Currently, due to a new policy of Wintergreen resort, unaccompanied guests (renters) are not allowed access to the gym, indoor pools or Devils Knob golf course.

Cleaning products • Garden view • Shampoo • Hot water • Free dryer – In unit • Body soap • Conditioner • Free washer – In unit • Hair dryer • Shower gel

Welcome to Tequila Sunrise! Located slope-side at Tequila and Lower Tyro, our home offers a true ski-in/ski-out experience—step outside and you're on the slopes!

Inside, you'll find an open floor plan featuring a fully stocked kitchen, a cozy family room that seats eight, and a huge wall of windows to watch stunning sunrises and skiers.

In warmer months, enjoy the double-level deck, perfect for relaxing with family and friends amidst beautiful views. Your unforgettable getaway awaits!

The space
Welcome to Our Home! Ideal for families with children or groups of friends, our comfortable house has plenty of beds for everyone. Located directly on the ski slope, you can ski right out the back door onto a blue run, surrounded by breathtaking mountain views.

Spanning 1,900 square feet, the main level has an inviting open floor plan with ample seating. Our kitchen is fully stocked with all the essentials, including a crockpot, blender, toaster, mixer, French press, coffee pot, and microwave—perfect for cooking, grilling, or entertaining. Relax in the living area with a 65" smart TV to access your favorite streaming services and enjoy fast Wi-Fi. Set the mood with candles in the fireplace (please do not start a fire!).

The upstairs loft features a double bed with a memory foam mattress, a cozy leather sofa (ideal for extra sleeping space), an additional TV, and a gaming system for entertainment.

In the basement you'll find three more bedrooms. The master suite has a queen bed, a standing desk, a full bath, and a lower balcony where you can catch the sunrise reflected in the mirrored armoire doors. The second bedroom offers two sets of bunk beds and its own full bath, with easy access to the back deck. The third bedroom features a lofted bed and a set of bunk beds, perfect for younger guests. All bedrooms have high-end mattresses and linens. Please note that the lower bedrooms do not have TVs.

A washer and dryer are available in the basement, with laundry detergent provided for your convenience.

Step outside to enjoy our upper deck with ample seating and a Big Green Egg grill. The lower deck features seating for six and a propane fire pit—an ideal spot for relaxing with friends over drinks.

Parking is easy with space for two cars directly in front of the house, and additional parking is available just a minute away in the Wintergreen lots.

Guest access
You'll have full access to the house except for one locked linen closet in the basement and a locked attic space in the loft.

Other things to note
For your safety, please refrain from using the fireplace. Instead, enjoy the cozy ambiance created by our remote-control candles. The lower deck features a propane fire pit for relaxing. Additionally, we have a Solo Stove available for use on the front deck only; please utilize the provided pavers to protect the wooden deck surface. Thank you for your cooperation!

Conditioner • Hair dryer • Shampoo • Bathtub • Free washer – In unit • Cleaning products • Body soap • Shower gel • Mountain view • Hot water

Welcome to The Ski House! Renovated ski-in/ski-out single family chalet on Eagle Swoop. Enjoy gorgeous, 50 mile+ views of the Blue Ridge from the back deck while taking a soak in the hot tub. Wake up early and enjoy an amazing sunrise. Walk to some of the best hiking trails and lookouts on the mountain. The location of this home simply cannot be beat! And WTG is now part of the Indy Ski Pass!

The space
The Ski House offers 1,250 sf of living space with high vaulted ceilings, two large bedrooms on the main level and a spacious loft on the second level, perfect for the kids! A modern kitchen stocked with everything one might need. We provide coffee beans, a grinder and a drip coffee maker. If you prefer Kuerig, we have one of those too... just please bring your own pods. Relax in the living room and cozy up in front of the stone, wood burning fire place. The bedrooms are furnished with comfortable, cozy beds, linens and towels for your use. There is a washer and dryer and we provide laundry detergent, dryer sheets, and dish washer detergent.

The living room and loft both have Smart TVs.

Guest access
You will have access to the entire house and deck. Enjoy the incredible views and, during ski season, the ease of skiing in and out of this private chalet. Off street parking for 3 vehicles. Sorry, no pets. HOT TUB: Please use the hot tub responsibly, and at your own risk. Follow all posted instructions and rules which can be found in the Welcome binder and within the home. Homeowners and Hosting Management Company are not responsible for any accidents or injuries which may occur from guest negligence. Thank you!

Other things to note
Wintergreen is a four-season resort. While there is plenty of skiing during the winter (a big welcome to Indy Pass holders, WTG recently joined the Indy community!) many other adventures can be enjoyed throughout the rest of the year. Miles of hiking trails, a beautiful golf course, tennis, Lake Monocan and the Discovery Ridge Adventure Center. When it is time to relax and rejuvenate, book a treatment at the Wintergreen Spa or try one of the two pools, Chestnut Springs and Rodes Farm on a warm, summer day (open from Memorial Day through Labor Day, 2-6pm daily). Rodes Farm also has tennis and archery. Venture off the mountain and visit a local brewery or winery... we are a short drive to Nelson 151 breweries, wineries, cideries and distilleries. Pick berries at Critzer family farm or plan a day trip to the Blue Ridge Tunnel, Natural Bridge, Luray Caverns, Sky Line Drive, Charlottesville or Staunton. There is so much to enjoy, all year round. *Please note, the Wintergarten Pool, hot tubs, fitness center, Devils Knob Golf and Tennis and Devils Knob Grill are only available to Wintergreen members. Lake Monocan is open to all guests Sunday through Friday, reserved for WTG members only on Saturdays.* (Open from Memorial Day through Labor Day)

Ski Information:
This home is right on the top of Eagle Swoop. This hill has THREE BLACK DIAMOND slopes (Big Acorn, Upper Sunrise and Sunrise Glades) and FIVE BLUE SQUARE slopes (Eagle Swoop, Upper Tyro, Lower Tyro, Tequila and Lower Sunrise) Please note, Black Diamond slopes are Most Difficult and for expert skiers only. Blue Squares are More Difficult. If Green Circle slopes are required for beginners, they can be found by the Resort just a very quick drive from the house.

When the trails are open, access is limited to ticketed skiers only. Wintergreen ski lift tickets operate using RFID cards which can be purchased or picked up at the resort ticket and rentals office. Visit the WTG website. Once purchased, these cards can then be reloaded online without having to go to the ticket window. If you do not have one of the reloadable cards and need to purchase a lift ticket, simply ski down the hill to the ticket office. From there, with a valid ticket/card you can start to use the chairlifts back up the mountain. When you want to take a break, simply step off of the Big Acorn chairlift and ski back to the chalet!

When the trails are not open for skiing, this is an excellent place to hike, enjoy a picnic lunch and take in the incredible views of the Blue Ridge!

Amenities:
The Market: Located at the corner of Mountain Inn Loop and Blackrock Drive. Just a short walk or drive from the house... Convenient market offering basic food staples and sundries, hot breakfast sandwiches and coffee, great lunch sandwiches and a selection of wine and beer.

Down the Mountain:
Blue Ridge Grocery (IGA) and Dollar General can be found in Nellysford on Route 151.

The Farmer’s Daughter Market
3079 Rockfish Valley Hwy, Nellysford, VA 22958


If you are planning a trip with a larger group and require the short term rental of a second property, please let us know and we can share the links to the other homes we manage.

For additional information on Wintergreen and surrounding area, please see the Guidebook that is included within this listing!

We look so forward to hosting you!

Free dryer – In unit • Hangers • Bed linens • Mountain view • Hair dryer • Cleaning products • Essentials • Hot water • Free washer – In unit • Extra pillows and blankets