Short Term Rentals
Bear Feet Retreat
Location: Wintergreen Resort, VA
Sleeps: 10 guests
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Situated on Devil's Knob golf course, close to restaurants, hiking, skiing, and tubing, you'll find there's plenty to do and see within walking distance of the property. The large kitchen and open living space is great for families to gather, and the dedicated game room provides entertainment even when the weather doesn't cooperate. This home features 4 bedrooms and 3 bathrooms!
Wintergreen Mountain Retreat
Location: Wintergreen Resort, VA
Sleeps: 8 guests
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​Forget your worries in this spacious and serene space. This newly remodeled 4-bed, 3-bath retreat offers a full kitchen, gas fireplace, outdoor deck with a beautiful view of the golf course. The downstairs features a primary bedroom with a king-size bed and a luxurious ensuite, as well as a guest bedroom with a queen-size bed and private bathroom. Two upstairs bedrooms feature queen-size beds with access to a shared bathroom. Two miles from slopes … your perfect mountain retreat awaits!
Treeloft 17: Ski in/Ski out
Location: Wintergreen Resort, VA
Sleeps: 8 guests
Pet Friendly!
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Ski chalet on Eagles Swoop ski slope. Recently renovated 3BR/3BA mountain top home nestled in the tree tops of Wintergreen Resort. Well-appointed with comfortable and relaxing furnishings, a well stocked kitchen, cozy bedding, 65” OLED TV, EV Charger, and a wood burning fireplace. The deck features a gas grill and bistro style lighting. This Treeloft home comfortably sleeps 2 couples + 4 kids or 3 couples. Ski in/Ski out convenience plus easy walk to views, hiking, resort, and dining.
Pepper's Mountain Pad
Location: Wintergreen Resort, VA
Sleeps: 6 guests
Pet Friendly!
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Welcome to Pepper’s Mountain Pad, nestled in the Blue Ridge Mountains at Wintergreen Resort. Within walking distance to all the resort attractions; this 2-bedroom, 2-bathroom mountain condo has so much to offer.
Mountain House Overlook
Location: Afton. VA (Blue Ridge Parkway)
​Sleeps: 5 guests
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​Unique octagonal house (2 bed, 2 bath) with stunning views of the Blue Ridge Mountains of Virginia. Located 2 miles from I-64, 15 minutes to downtown Waynesboro and an easy 25 min drive to Charlottesville and UVA. Open floor plan, perfect for gathering, and long-range 180 degree views from nearly every room. Fully equipped renovated kitchen. Quality linens and bedding. Rustic, yet modern decor. Home features large fireplace, outside fire pit, wifi, and board games galore. Stargazing and birdwatching heaven.
Greyhaven II
Location: Wintergreen Resort, VA
Sleeps: 11 guests
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Relax with the whole family at this 4 bed, 3.5 bath peaceful place to stay. Located at the top of the mountain a little over a mile from Wintergreen Resort, this house is the perfect escape! Close to skiing, golf, wineries, breweries, and hiking there is something for everyone. Or relax at home on the deck, warm yourself by the fire, and enjoy the closet full of games, puzzles, and DVDs! There is even a secret nook just for the kids! The house is also equipped with Wi-Fi for all of your streaming needs.
Find YOUR Magic
Location: Wintergreen Resort, VA
Sleeps: 12 guests
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This 5 bedroom, 3 bathroom cozy cabin allows you to unplug, unwind, soak up the mountain air and find the magic with the ones you love to travel with. Centrally located with just a short walk to the main Wintergreen Resort, market, and an abundance of hiking trails including "The Plunge". This cozy cottage won't disappoint and has ample room for everyone. It is also walkable to the ski slopes (Tyro) in the winter!
The Bear Witch
Location: Wintergreen Resort, VA
Sleeps: 10 guests
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​Bring the whole family to this great place with lots of room for fun. This home features 4 bedrooms and 4 bathrooms, sleeping up to 10 guests. Recently renovated with new HVAC, hot tub and decks, pool table, poker table, new bedding and TV in each bedroom, well supplied kitchen, 72" TV and beautiful view of the forest.
Fairy Tale House
Location: Wintergreen Resort, VA
​Sleeps: 7 guests
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​Come to this 3 bedroom, 2.5 bathroom home and relax by the cozy gas fireplace, enjoy a hot chocolate after hiking one of the many trails at Wintergreen or a long day of skiing. This home is perfect for families. Sit on the deck and enjoy the private wooded views while you grill up dinner. Very close proximity to the lodge, slopes and hiking.
The Hideaway at the Waterfall
Location: Wintergreen Resort, VA
​Sleeps: 11 guests
​Pet Friendly!
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The Blue Ridge Mountains are calling you to this 3-level, 4 bed/3 bath home for an epic getaway! A family-favorite rental, this home is nestled in the woods at the top of Wintergreen Resort. It brings the perfect balance of comfort & privacy while conveniently located near skiing, golf, & wineries/breweries. Enjoy the woods & a stream from the 180-degree deck with hikes to the AT and a waterfall right out the door.
Positive Altitude
Location:Wintergreen Resort, VA
Sleeps: 10 guests
Pet Friendly!
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You won’t be able to look away from the spectacular Shenandoah Valley and Blue Ridge mountain views offered by this Wintergreen townhouse located 3,600 feet up at the top of the mountain! Enjoy hanging out on the two decks staring out at the spectacular scenery after long days full of skiing, hiking and exploring all that Wintergreen has to offer. With 5 bedrooms and 4.5 bathrooms there is tons of room to bring all your family and friends. The kitchen is fully equipped to prepare your favorite meals. Watch the sunset as you sit in front of the fire and make s'mores. Pets are welcome:) This is one spot guaranteed to leave you with a ‘Positive Altitude!’
Oh Deer
Location: Wintergreen Resort, VA
​Sleeps: 16+ guests
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​OH DEER! Welcome to your perfect escape in the Blue Ridge Mountains! Nestled just steps from the slopes of Wintergreen Ski Resort, our uniquely designed home offers a cozy, family-friendly retreat with all the charm of a luxury lodge--PLUS a creative twist. Each room is inspired by a different aspect of the Wintergreen experience, bringing the mountain magic indoors.
Mountain Retreat
Location: Wintergreen Resort, VA
Sleeps: 8 guests
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​Highly reviewed home relisted under experienced management. Our 3-bed, 3.5-bath home at the top of Wintergreen is only a short walk to reach Wintergreen’s vast trail system and just a short drive to the ski slopes. For a little luxury after your day’s adventure, treat yourself to an evening soak in the home's hot tub, followed by a leisurely 1/4-mile walk to the neighborhood overlook, where mountain views appear endless, or just sit by a cozy fire in our great room.
Peaceful Mountain Home
Location: Wintergreen Resort, VA
​Sleeps: 8 guests
Pet Friendly!
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Charming 3-bedroom, 2.5 bathroom mountain retreat at the top of Wintergreen Resort. Peaceful and private location. Relax in front of the gas fireplace, soak in the hot tub, or sit on the deck and enjoy the views. Spend your day hiking a nearby trail and enjoy visiting local restaurants, breweries, and wineries. Kitchen is fully stocked and there is a new gas grill on deck. Kids will love the upstairs twin bedroom, complete with a play area with books & toys. Separate den with TV and workspace on lower level.
23 Trillium
Location: Wintergreen Resort, VA
​Sleeps: 10 guests
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This stylish, newly remodeled 4br/4ba home is the perfect getaway you have been looking for, in any season! The home has been fully restored with amazing upgraded amenities, yet it retains the simple charm of a mountain getaway. Located on the 16th green of a public course and incredibly close to 37 miles of hiking and biking trails, downhill and cross-country skiing, and Nelson County's 7 wineries, 4 breweries, 3 cideries, and 2 distilleries, this home offers plenty of options for adventure!
The Rockfish Retreat
Location: Wintergreen Resort, VA
​Sleeps: 9 guests
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Sit back, relax, and soak in the views. The 3 bedrooms, 2.5 bathroom Rockfish Retreat is nestled in the foothills of the Blue Ridge Mountains, right in the heart of the Nelson 151 Winery/Brewery Trail. And it has everything you need for a fun and relaxing family get away: hot tub; fire pits, walking trail, toys/games, high-speed fiber internet, and most importantly, peace and quiet. We love the time that we get to spend in Afton and hope you do too!
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Relaxing Cabin in the Woods
Location: Wintergreen Resort, VA
Sleeps: 6 guests
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Welcome to our home! This beautiful 3 bedrooms, 2.5 bathroom mountain cabin is located on the top of Wintergreen Resort, and we are pleased to offer your family the same stress free, relaxing getaway we love to come enjoy! It is in a great location with easy access to skiing, snow tubing, outdoor swimming pools and tons of hiking trails right out the front door. The Mountain Inn and Conference center are also a short distance away.
Slope-Side with a Mountain View
Location: Wintergreen Resort, VA
Sleeps: 6 guests
Pet Friendly!
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This beautiful 3 bedrooms, 3 bathroom Dobie condo unit in Wintergreen Resort will give you views of peace and serenity with all the adventure of the outdoors at your fingertips! This third floor condo unit has the most breathtaking views. It is within sight and a short walking distance to the Mountain Inn and local restaurants.
Wintergreen Condo Ski-in/Ski-out
Location: Wintergreen Resort, VA
Sleeps: 6 guests
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​Come enjoy this beautiful 3 bedroom, 2 bathroom condo home that's right on the slopes, not to mention centrally located for all the fun at Wintergreen. Not only is this home beautiful, but it also has all the necessities for the perfect getaway!
On the Mountain Condo
Location: Wintergreen Resort, VA
Sleeps: 6 guests
Pet Friendly!
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Come relax in this 2 bedroom, 2 bathroom home! Families of all ages will love exploring the area and all it offers; golf, ski, hiking, wineries. Walk to dog park, hiking trails, Nature Center, and Wintergreen Village. Golf course view featuring FAST Wi-Fi and fireplace. It is ~10 minute walk to top of Highlands lift or a 4 minute drive to top of main mountain. You also have access to Rhodes Farm and Chestnut Springs pool in the afternoon in summertime.
Condo with Valley Views
Location: Wintergreen Resort, VA
Sleeps: 4 guests
Come forget your worries in this spacious and serene space on top of the mountain at Wintergreen Resort. This 2-bedroom, 2 bath condo features Smart TVs, free WiFi, a great kitchen with all new appliances and more to ensure a restful stay. Sit on the balcony overlooking Rockfish Valley and the Blue Ridge Mountains while sipping wine or beer from one of the many vineyards and breweries in the area. Dogs are welcome to join you on adventures down the many nature trails!
You'll say "Wow" over this View!
Location: Wintergreen Resort, VA
Sleeps: 4 guests
Welcome to your perfect mountain getaway! Our recently renovated 2-bedroom, 2-bathroom condo offers breathtaking ridge views and all the comforts of home. With two king beds, a fully stocked kitchen, and modern amenities like WiFi, air conditioning, and an in-unit washer/dryer, this is the ideal retreat for your next adventure—whether it's skiing, hiking, or simply relaxing in nature.
Little Bear
Location: Wintergreen Resort, VA
Sleeps: 9 guests
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Welcome to Little Bear (4 bed, 4 bath)! We'd love to provide you with a comfortable stay and clear views so you can enjoy the beauty of the Blue Ridge Mountains!
At Little Bear you will enjoy views down the Blue Ridge Mountain and into the valley. Private street, directly off the hiking trails, and close to the mountain loop, tubing park and Devil Knob Golf course, this is a perfect place for all that Wintergreen has to offer.
Ryders Ridge
Location: Wintergreen Resort, VA
Sleeps: 10 guests
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Welcome to Ryder's Ridge, a designer-decorated 4 bed, 3.5 bath home on a quiet street in Wintergreen with amazing mountain views! Watch the sunset on our expansive back deck with propane firepit, or soak in the brand new hot tub. Inside, you'll love the open floor plan with year-round views, 12' ceilings, and 3200 square feet of professionally designed furnishings. Plus, have some fun in the game room downstairs!
The Pond at Owl Hollow
Location: Lovingston, VA
Sleeps: 6 guests
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Enjoy a secluded getaway nestled in the Blue Ridge Mountains. Owl Holler is 30 minutes south of Charlottesville, under 3 miles to Lovingston Vineyards, and close to other vineyards, breweries, a whiskey distillery and historic Lynchburg. The handbuilt 3 bedroom 2 bath unit is located on 23 acres with a pond, a hiking trail, a fire pit and a balcony with beautiful views. Listen to the owls, look at the stars through our telescope or play on our Ms. Pacman game. Fiber optic cable and internet.
Three Ridge Retreat
Location: Wintergreen Resort, VA
Sleeps: 4 guests
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​Your family will be close to everything when you stay at this centrally-located retreat. A short walking distance to the lodge, restaurants, gift shops, and ski slopes! Beautiful landscapes for hikes and a short drive to Sherando lake and Lake Monocan for summer swims and fishing. Two pools are available for guests to use during the summer. Close to the brewery/winery/distillery trail which is home to names such as Bold Rock and Three Notched. Dog friendly!
Morse Manor
Location: Amherst, VA
Sleeps: 6 guests
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Come relax and enjoy a night under the stars at this cozy 3 bedroom, 2 bathroom home. Gather with family and friends for a vacation or getaway from everything.
The Colleen Cottage
Location: Arrington, VA
Sleeps: 6 guests
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Relax with the whole family at this peaceful place to stay. Big yard for kids to play and patio to sit, chat, and relax.
Located a minute off 29. Saunders brothers orchard, Drumhellers orchard, and Seaman’s orchard are very close by!