Vacation Home Rentals By Owner In Wintergreen Resort, VA

$343.15

Family Friendly Mountain Home! Great Location on Devils Knob

Wintergreen Resort, Virginia, United States

Beautiful family friendly mountain home in a great location within the Wintergreen Resort on the prestigious Devil’s Knob loop. A few minutes’ walk to the Wintergreen Spa, several hiking trails, and the Nature Foundation Center! Only one mile from the Wintergreen Mountain Inn, the Market, skiing, tubing, snowboarding, and multiple restaurants!brbrThere are also many wineries and breweries in the area and the Blue Ridge Parkway is only a few minutes away, as well!brbrIn addition to its great location, the house has an ideal open floor plan that is perfect for any family gathering. brIts main floor includes the living room, dining room, and kitchen are all connected as one, open living area in a beautiful spacious setting. It also includes 3 bedrooms/2.5 bathrooms; Master Suite w/private bathroom/jetted tub/King size bed, Second Bedroom: King size bed, Third Bedroom: Queen bed and a Day BedbrThe Upstairs Den is perfect for either the children or visiting families. It is a spacious open area that has a bunk bed, a day bed w/ trundle, a pull-out sofa bed, recliner chairs and another full-bathroom.brGuests can enjoy the outdoor patio, spacious deck, beautiful front porch, the outdoor fire pit in such a lovely and relaxing setting! Also enjoy the basketball hoop and corn hall game.brThis quiet, beautifully decorated mountain home offers all the necessary amenities to make your stay as comfortable as possible. brbrAmenities: brHigh-Speed Internet, 2 Smart TV, Xbox w/games (you can also bring your own favorite games), and a Foosball table.brA washer/dryer, fully equipped kitchen, dishwasher, microwave, crock-pot, toaster, coffee machine and KeurigbrMassage Chair (use under your own discretion)brOutdoor fire-pit, heater, Charcoal Grill, Electric Grill brThis cozy house is also stocked with plenty of games, movies, and books for everyone to enjoy!brbrWe provide hand soaps, paper products, and laundry/dish washing detergents. We have electric grill and a charcoal grill (Bring your own charcoal)brbrAREA ATTRACTIONS: brThree Ridges Overlook (0.5 miles), Blue Ridge Parkway (4.5 miles), Shenandoah National Park/Skyline Drive-Rockfish Gap (18 miles)brLake Sherando and Lake Monacan (canoeing, kayaking, biking, fishing, sand volleyball court, sandy beach, and picnic areas)brDAY TRIPS: Charlottesville (45 miles), Richmond (110 miles), Washington, D.C. (150 miles)

4

Bed

3

Bath

10

Sleeps

$652.03

/ Nightly

Private Vacation Home

Mountain Escape: Golf, Hiking, Hot Tub & Scenic Views at 5BR Wintergreen Home

Wintergreen Resort, Virginia, United States

The Hot Tub Time Machine is a beautiful 5 bedroom, 4 bathroom home that sleeps 12 located in the Blue Ridge Mountains of Virginia on the 12th Fairway of Devil’s Knob Golf Course in Wintergreen Resort. brbrThe Hot Tub Time Machine boasts beautiful seasonal views of the Shenandoah Valley and is within 1 mile of most amenities includes golf, tennis, snow skiing, swimming, hiking, restaurants and the WinterGarden Spa. brbrA 6 person hot tub is provided for year round fun and relaxing. A gas grill is provided. brbrImportant things to note: brPlease note that fireplaces are not available for guest use. brDue to allergies, this property is not pet friendly. brPlease do not wear ski/snowboard boots and dirty hiking boots in the house. brNo skis or snowboards in the home. There is a ski closet on the front of the house that will hold these items.brPlease clean and cover the grill after use. For the sake of the wildlife (especially bears), DO NOT LEAVE FOOD OR TRASH OUTSIDE! Lock all cars and house doors!brSince we do not live on the mountain full time, we do have outdoor only security cameras on the property. brAs you plan your trip to the mountains, please remember we do get rain, snow, ice, some foggy days, and some occasional inconveniences which are out of our control. Winter weather in the Blue Ridge Mountains can occur from November through April. The mountain roads can be icy and could be dangerous in winter weather. For the safety of you and your party, please be prepared to drive in snow and/or ice during these months. This means 4-wheel drive/AWD, good tires, and/or chains. We cannot give refunds due to weather.brbrProperty layout is as follows:brUpper Level – 1 Queen bedroom, Twin bed, full bathroom with shower.brMiddle Level – Living Room, Dining Room, Kitchen, access to rear deck, King bedroom with full bathroom including Tub/Shower combination. brLower Level – King Bedroom, Queen Bedroom, Twin Bunk and standalone twin bed bedroom, 2 full bathrooms with tub/shower combinations, Laundry RoombrbrThings to Do:br-Wintergreen Resort: ski, golf, tennis, spa, nature center, restaurants, br-Pools: As our guest you’ll have free access to 2 outdoor pools (Memorial Day to Labor Day); Chestnut Springs on the mountain (heated) with a pavilion area. You also also have free access to the Rhodes Farm outdoor pool, pavilion area, tennis court, volleyball pit, horseshoe area at Stoney Creek, Wintergreen’s property just down the mountain in the valley. br-Lake Monacan: located in Stoney Creek just down the mountain in the valley. Fee for use available Sunday through Friday.br-Outdoors: Minutes from the Upper Shamokin Falls Trail, a family friendly hike with amazing waterfalls; just a few mile from Skyline Drive/Blue Ridge Parkway; multiple mountain biking trails.br-Adulting: 151 craft beverage trail that features multiple wineries, cideries, a distillery, a meadery, and breweries/restaurants.br-Children: Trillium Nature Center, Treehouse, Discovery Ridge Adventure Center (rock climbing wall, ninja warrior course, mini golf, bungee jumping). br-You will have full access, at regular resort prices, to all other resort facilities including but not limited to skiing, golf at Stoney Creek, dining, the spa and all other activities, with the following limitations:br- The WinterGarden Aquatics and Fitness center may be used as part of a spa treatment at the WinterGarden Spa.brbrInternet: High Speed WiFi

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Bath

Sleeps

$287.81

/ Nightly

Private Vacation Home

Mountain home close to resort, trails, breweries, & more!

Wintergreen Resort, Virginia, United States

3-story single-family mountain chalet on a quiet street at Wintergreen Resort. King master en suite on third floor with Mountain View’s, Queen bdrm downstairs next to bunk room w/ two bunks - full on bottom & twins on top (total 4 beds in bunkroom). 2 story great room with towering stone fireplace adjacent to kitchen, dining room, large deck, and foyer half bath. Please note home does not have air conditioning. Temps are generally 20 degrees cooler than off the mountain. Shady tree cover and plenty of fans.We have access to the Chestnut Springs outdoor pool seasonally from 2 to 6pm.brbrFour-season resort with hiking, golf, horseback riding, watersports, fishing, hiking, pools and a lake with beach. In winter skiing, snowboarding, and tubing. Close to resort shops, restaurants and bars. 10 minutes to breweries, wineries, distilleries, antiquing, parks and more. Tons of great hiking trails near!brbrGuests can enjoy two swimming pools–Chestnut Springs on the mountain brand Rodes Farm in the valley. The two pools are in well-landscaped settings and offer large pavilions which can be reserved for private parties. Both sites have playgrounds for children. Both pools restrict guests to afternoon hours.brbrRodes Farm also has a park with picnic tables, a pond, a joint pickleball and tennis court and horseshoes as well, plus an archery range managed by the Wintergreen Sporting Club. brbrBring your bikes, this is one of the flattest streets at Wintergreen and ends in a cul-de-sac, perfect for little ones who want to bike all day long.brbrHiking trails galore, both within walking distance, and a short drive away.brbrLarge wrap-around front porch with grill, deck chairs, hammock, and sunset and sunrise views. brbrGolf year round in the Rockfish River valley on our nationally ranked Stoney Creek Golf Course, and you'll discover why Conde Nast Traveler magazine selected Wintergreen as one of the Top 50 Golf Resorts in the World. Upon completion of this gem, the Open Doctor Rees Jones remarked, I think what Stoney Creek is to me, is one of the great settings in mountain golf. And why not Offering spectacular vistas of the Blue Ridge Mountains, the Monocan, Shamokin and Tuckahoe nines wind their way through the Rockfish Valley and combine to make this a contemporary design classic. With elevation changes, contoured greens and the occasional side hill lie, Jones brought the natural elements of the landscape into play: meandering streams, hardwood forests and pristine wetlands.brbrWintergreen Resort features Lake Monocan, a private lake tucked into the Rockfish Valley at the base of the mountain. Lake Monocan is a 20-acre lake perfect for swimming and cooling off during the summer months. Guests can relax and play on the sandy beach area, pack a picnic to enjoy in the shaded picnic area. A larger pavilion is available to rent for private parties or events. Watercraft rentals including paddleboards, kayaks and aquabikes are available for rent so guests can explore the entire lake. The Beach Hut can answer any questions and offers snacks and drinks for sale. There are convenient restrooms with showers available for lake-goers. Guests are permitted to bring their own beach chairs, shades, kayaks or paddleboards.brbrDiscovery Ridge Adventure Center at Wintergreen Resort is where your family vacation begins, with indoor and outdoor fun for the entire family. Experience a thrilling Blue Ridge family vacation in the mountains - with a host of activities that will satisfy even the most adventurous spirit. Archery - think Hunger Games, Robin Hood, your childhood summer camp! Test your skill with a bow & arrow. Bungee trampoline - a hybrid trampoline / bungee apparatus, enabling jumpers to reach heights of 25 feet and higher. brbrClimbing tower - a 25-foot structure with a belay apparatus on top, featuring varying degrees of difficulty. brbr4 TV's, board games, playing cards, puzzles, books, well equipped kitchen allows you to cook and dine on site. Large screen television for movies at night. brbr3 minute drive to Wintergreen shops, restaurants, and attractions and so much more within easy drive https://www.nelson151.com/map/brbrFor your convenience, we provide firewood, linens and towels and a starter supply of toilet paper, paper towels, trash bags, dish detergent, laundry detergent and hand soap.brbrOn the mountain, we are a short drive to The Market, The Edge, Mountain Inn, Wintergarden Spa, the Discovery Ridge Adventure Center, ski slopes, and The Plunge Tubing Park. brbrOff the mountain, enjoy the many local breweries, wineries and restaurants - Short drive to Devils Backbone Basecamp and Brewpub, Bold Rock Cidery, Ski Barn for ski rentals, Blue Ridge Pig for barbecue, Black Bear Creamery for ice cream, Basic Necessities for brunch, lunch and dinner, & Chirios Pizza for pizza (they deliver!) There is also a grocery store, ABC Store, Dollar General, pharmacy, and antiquing in Nellysford.brbrShort drive, 3 minutes, to the slopes. Ski boot and glove dryer included! Gorgeous floor to ceiling stone fireplace is center piece of cozy living room. Apres Ski in front of fire while enjoying both sunrise and sunset views.brbrThe Plunge is Virginia's largest tubing park. Imagine being on top of a ten story building and looking out over a hill that's longer than three football fields. Now imagine going downhill on a tube at speeds reaching 30 mph. That's The Plunge! Thrills and chills without the spills. To make it even easier, our conveyor lift will bring you and your tube comfortably and quickly back up the hill so you can do it again and again. Some of our guests call it the scream machine and we think you'll agree! It's just plain tubular fun. Because after all, anyone can slide!

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Bath

Sleeps

$437.97

/ Nightly

Private Vacation Home

Calm Creek Retreat - minutes from slopes, hot tub, large cozy family room!

Wintergreen Resort, Virginia, United States

After a day on the slopes, return to Calm Creek Retreat for a relaxing hot tub soak and cozy night in by the fire!brbrStep into this spacious home with open first floor - great for gathering with family and friends. Well stocked kitchen with dishes and cookware, large shaded deck with a grill and dining area, soak in the hot tub or enjoy the rocking chairs by a fire pit and listen to the babbling brook as you take in the scenes of the 7th fairway of Devil’s Knob golf course. Brand new comfy couch to relax in front of the fireplace and watch a movie on multiple provided streaming services. brbrThe house has two bedrooms with king beds and two bedrooms with queen beds. Downstairs there is a half bath adjacent to the entry and a Jack and Jill style bathroom with private sink areas and a shared toilet/bathing area between a king and queen bedroom. Upstairs, the king and queen bedrooms each have a private bathroom with the queen bathroom also having a hall entrance for anyone sleeping on the queen sofa bed in the loft to use. There are room darkening/noise muffling curtains that can be pulled across the opening of the loft for privacy. There are balconies off of each king bedroom. brbrThe house is minutes from multiple popular hiking trails of various degrees of difficulty. Guests are welcome to use an assortment of games, puzzles and DVDs. brbrWasher/dryer available. Please bring detergentbrbrFor security purposes, this property has a doorbell camera at the front entrance and a security camera overlooking the side yard/corner of back deck

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Sleeps

$688.38

/ Nightly

Private Vacation Home

Hot Tub / Bunk Room / EV Charger / King Beds / 3,200 sqft

Wintergreen Resort, Virginia, United States

Welcome to Adrian's Den, a cozy mountain retreat nestled in the heart of Wintergreen Resort. Enjoy not only close proximity to the slopes, but dozens of other all-season amenities.brbr•1mi Walk to Ski Check-inbr•Level 2 EV Charger br•Off-street Parking (5 cars)br•Washer/Dryerbr•Private Hot Tubbr•2 Fireplacesbr•Outdoor Fire Pitbr•Exercise Equipmentbr•4 Br/3 Ba, 3200 SqFtbr•2 King Beds, 1 Queen Bed, 3 Bunk Bedsbr•Multiple Living Spacesbr•High Speed WiFibr•Smart TVsbr•Dimmable Lightsbr•JBL Bluetooth Speakerbr•Ideal Locationbr•Nearby Trails & Overlooks

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Bath

Sleeps

$574.42

/ Nightly

Private Vacation Home

Trail Magic- Sk-in & Ski-out

Wintergreen Resort, Virginia, United States

Summary:brbrTrail Magic | Ski-In/Ski-Out Lodge at Wintergreen Resort with Hot Tub brbrbrbrExperience the magic of the mountains at Trail Magic, a true ski-in/ski-out retreat located in the heart of Wintergreen Resort. This full lodge-style home is designed with comfort, convenience, and year-round adventure in mind. Bring the whole family to this great place with lots of room for fun.brbrbrbrThe Space:brbrWelcome to Trail Magic – Your Ski-In/Ski-Out Mountain Escape at Wintergreen ResortbrbrbrbrNamed after the Appalachian Trail tradition of “trail magic.” Those unexpected moments of kindness and comfort hikers experience along their journey. This luxury retreat is designed to offer the same surprise-and-delight feeling. Whether you're skiing straight onto the slopes or soaking in the hot tub with a glass of wine, you'll find your own version of trail magic here.brbrbrbrLocated directly on Eagle’s Swoop, this ski-in/ski-out home sits in the heart of Wintergreen Resort with adventure at your doorstep all year long. In winter, step outside and hit the slopes; in warmer months, explore nearby hiking trails, scenic overlooks, and the natural beauty of the Blue Ridge Mountains.brbrbrbrProperty Highlights:brbrbrbr- 4 spacious bedrooms, each with connecting en-suite bathroomsbrbrbrbr- Private hot tub with winter mountain viewsbrbrbrbr- Outdoor fire pit, perfect for post-adventure gatheringsbrbrbrbr- Bright, open living spaces with floor-to-ceiling windowsbrbrbrbr- Direct access to Eagle’s Swoop ski trailbrbrbrbr- Lower level includes a boot warmer and ski lounge area, perfect for drying off and stashing your gear in comfort.brbrbrbr- Close to hiking, dining, wineries, and resort amenitiesbrbrbrbrWhether you’re coming for a ski weekend, a mountain getaway, or a peaceful escape, Trail Magic invites you to relax, recharge, and experience a little unexpected magic.brbrbrbr***Same-Day Bookings: Please contact the host prior to booking to confirm the home has been cleaned and is available.***brbrbrbr***Minimum Booking Age: 24+brbrWe kindly request that no parties take place, and guests must be 24 years of age or older to book the home. Thank you for your cooperation!brbrbrbrGuest Access:brbrGuest has access to whole propertybrbrbrbrThe Neighborhood:brbrWintergreen Resort:brbrbrbrPerched on 11,000 breathtaking acres along the eastern slopes of the Blue Ridge Mountains, Wintergreen Resort is a true four‑season playground. Surrounded by winding trails, cascading streams, and lush forests, it’s the perfect place to unwind, explore, and reconnect with nature. Here you’ll find endless possibilities—whether you’re chasing outdoor adventure, indulging in relaxation, or gathering with family and friends.brbrbrbrIn winter, carve through fresh powder with skiing (steps away from the house), snowboarding, and snow tubing. When the weather warms, tee off on 27 holes of championship golf at the Stoney Creek Course, play on award‑winning tennis courts, hike scenic mountain trails, cast a line fly fishing, or cool off with a refreshing swim. Pamper yourself at the full‑service mountaintop spa, then enjoy a variety of delicious dining options.brbrbrbrWhether you come for the crisp mountain air, the sweeping views, or the countless activities, Wintergreen Resort offers a refreshing escape and unforgettable memories in every season.brbrbrbrGetting Around:brbrNeed transportation or trip planning brbrWe work with a private concierge service that will make your getaway effortless. Offering private transportation, wine and brewery tours, in‑home chefs, spa services, yoga, grocery delivery, and more. They’ll create a personalized experience so you can simply relax and enjoy. Ask host for more info.brbrbrbrOther Things to Note:brbrWintergreen Ski Resort offers 26 runs across 129 skiable acres, vibrant après‑ski dining, night skiing on 45 acres, and Virginia’s largest snow tubing hill—The Plunge brbrbrbrDiscovery Ridge Adventure Center features rock climbing, bungee trampolines, a 25‑ft climbing tower, gem mining, disc golf, 18‑hole mini golf, ninja course, archery, and mechanical bull rides.brbrbrbr- Wintergreen Activities (On‑Site & Nearby)brbrbrbrEagles Edge Ski Slope - Just a couple steps away!brbrbrbrWintergreen Ski Resort Base Lodge – 3 minbrbrbrbrThe Plunge Snow Tubing Park – 3 minbrbrbrbrDiscovery Ridge Adventure Center – 3 minbrbrbrbrWintergreen Resort Tennis and Pickleball Courts - 6 minbrbrbrbrShamokin Springs Nature Preserve – 8 minbrbrbrbrStoney Creek Golf Course – 21 minbrbrbrbr- Nearby AttractionsbrbrbrbrAppalachian Trail Head – 15 minbrbrbrbrBlue Ridge Parkway – 8 minbrbrbrbrThree Ridges Overlook – 10 minbrbrbrbr Wine & BeerbrbrDevil’s Backbone Brewpub – 15 minbrbrbrbrThree Notch’d Brewing - 20 minbrbrbrbrHill Top Berry Farm & Winery – 20 minbrbrbrbrBold Rock Nellysford Cidery - 20 minbrbrbrbrWood Ridge Farm Brewery – 35 minbrbrbrbrSeven Arrows Brewing Company – 35 minbrbrbrbrBlue Mountain Brewery – 40 minbrbrbrbrVeritas Vineyards & Winery – 40 minbrbrbrbrAfton Mountain Vineyards – 40 minbrbrbrbr Hiking HighlightsbrbrHighlands Leisure Trail – 4 minbrbrbrbrUpper Shamokin Falls Trail – 5 minbrbrbrbrAppalachian Trail – Three Ridges Hike – 10 minbrbrbrbrCrabtree Falls – 35 minbrbrbrbr✈️ AirportbrbrCharlottesville–Albemarle Airport – 1 hrbrbrbrbr Water & Pool AccessbrbrChestnut Springs Pool (on‑mountain) – 5 minbrbrbrbrRodes Farm Pool (valley) – 25 minbrbrbrbrLake Monocan (Stoney Creek) – 25 minbrbrbrbrSherando Lake Recreation Area – 30 minbrbrbrbrbrbrWater Activities & Pool AccessbrbrGuests may use the HOA pools at Chestnut Springs (on‑mountain) and Rodes Farm (valley) from Memorial Day weekend through Labor Day. brbrbrbrLake Monocan (20-acre resort lake at 239 Camping Ridge Lane, Stoney Creek) offers swimming, aqua cycles, paddleboards, kayaks, snack bar, and grills; day-use fees please check on Wintergreen Resort Website. brbrbrbrSherando Lake Recreation Area features a scenic 25-acre spring-fed lake with sandy beaches, shaded picnic areas, rustic architecture, and adjacent trailheads. Day-use is $8 per vehicle (up to eight passengers).brbrbrbrImportant Resort Policy Update:brbrAs of newly enacted Wintergreen Resort policy: unaccompanied guests (renters) cannot access the gym, indoor pool, or Devils Knob golf course.brbrbrbrInteraction with Guests:brbrTrail Magic has a wonderful team. We want all our guest to have a 5 star experience. Customer service is important to us. Holly will be your main point of contact for bookings, questions, planning, check-in, and through your stay!

Bed

Bath

Sleeps

$708.57

/ Nightly

Private Vacation Home

Art & Soul: Sauna/Hot Tub & EV Charger/Hammocks

Wintergreen Resort, Virginia, United States

Welcome to Art & Soul, a newly renovated and stairless entry home in the picturesque mountains of Wintergreen, Virginia. This enchanting retreat is a perfect blend of comfort and creativity, offering an inviting atmosphere that inspires relaxation and rejuvenation. Located in the Wintergreen Resort, this home offers convenient access to skiing, hiking, and a variety of outdoor activities. This home is all 1 level with NO stairs - perfect for the entire family! brbrLiving Room: Spacious and inviting with large windows, cozy seating area with a fireplace, coffee table and bookshelf filled with local art and board games, Smart TVbrbrDining Room: Large dining table seating up to 10 guestsbrbrKitchen: Fully equipped with modern appliances (refrigerator, stove, oven, microwave, dishwasher), ample counter space and breakfast bar with stools, coffee maker, toaster, and cookware providedbrbrBedroom 1: King bed, nightstands with lamps, smart TV, lounge chairbrbrBathroom 1: En-suite bathroom for bedroom 1 with double vanity, walk-in shower shower and soaking tub brbrBedroom 2: King bed, nightstand with lamp, lounge chair, smart TVbrbrBathroom 2: Hall bathroom with single vanity and walk-in showerbrbrBedroom 3: 2 Queen beds, nightstand with lamp, dresser, smart TVbrbrBathroom 3: En-suite bathroom for bedroom 3 with single vanity and walk-in shower showerbrbrOutdoor Deck: Expansive deck with panoramic mountain views, dining area with outdoor furniture and grill, lounge chairs for soaking up the sun (Swim spa is currently NOT operational)brbrSauna: located near the deck for easy access, plus an outdoor shower to rinse offbrbrHot Tub: we have a new saltwater hot tub available for guests to use.brbr**FREE boot warmers available for guests to use**brbrNearby Attractions:br- WTG Slopes - 5min drivebr- Blue Ridge Parkway - 7min drivebr- Devils Backbone Basecamp - 11min drivebr- Blue Toad Hard Cider - 11min drivebr- Bold Rock Cidery - 12min drive brbrDOG FRIENDLY home with an extra $75 fee/stay. NO cats, fines apply!brLiving Room: Spacious and inviting with large windows, cozy seating area with a fireplace, coffee table and bookshelf filled with local art and board games, Smart TVbrbrDining Room: Large dining table seating up to 10 guestsbrbrKitchen: Fully equipped with modern appliances (refrigerator, stove, oven, microwave, dishwasher), ample counter space and breakfast bar with stools, coffee maker, toaster, and cookware providedbrbrBedroom 1: King bed, nightstands with lamps, smart TV, lounge chairbrbrBathroom 1: En-suite bathroom for bedroom 1 with double vanity, walk-in shower shower and soaking tub brbrBedroom 2: King bed, nightstand with lamp, lounge chair, smart TVbrbrBathroom 2: Hall bathroom with single vanity and walk-in showerbrbrBedroom 3: 2 Queen beds, nightstand with lamp, dresser, smart TVbrbrBathroom 3: En-suite bathroom for bedroom 3 with single vanity and walk-in shower showerbrbrOutdoor Deck: Expansive deck with panoramic mountain views, dining area with outdoor furniture and grill, lounge chairs for soaking up the sun (Swim spa is currently NOT operational)brbrSauna: located near the deck for easy access, plus an outdoor shower to rinse offbrbrHot Tub: we have a new saltwater hot tub available for guests to use.brbr**FREE boot warmers available for guests to use**brbrNearby Attractions:br- WTG Slopes - 5min drivebr- Blue Ridge Parkway - 7min drivebr- Devils Backbone Basecamp - 11min drivebr- Blue Toad Hard Cider - 11min drivebr- Bold Rock Cidery - 12min drive brbrDOG FRIENDLY home with an extra 75 USD fee/stay. NO cats, fines apply!

3

Bed

3

Bath

8

Sleeps

$430.02

/ Nightly

Private Vacation Home

Private Mountain Getaway | Wintergreen Resort

Wintergreen Resort, Virginia, United States

Summary:brbrUnplug and unwind at 'Sunny Bear 'at Wintergreen Resort, VA. A peaceful mountain retreat tucked away yet close to resort amenities. Perfect for families, couples, or friends, this home features a stunning floor-to-ceiling stone fireplace, spacious decks for morning coffee or stargazing, and plenty of space to relax and reconnect. With seasonal pool access, skiing, winter activities, tennis, pickleball, and Appalachian Trail hiking nearby, it’s the perfect blend of comfort, nature, and adventure.brbrbrbrThe Space:brbrSunny Bear is a welcoming mountain home where families and friends can relax, reconnect, and enjoy time together at Wintergreen Resort. Set in a peaceful area of the resort, the home feels tucked away while still offering easy access to year-round activities.brbrbrbrInside, the open living space invites everyone to gather around the floor-to-ceiling stone wood burning fireplace after a day of skiing, hiking, or exploring the mountains (firewood provided). The kitchen and dining area are designed for shared meals, games, and easy conversation.brbrbrbrThe home offers three bedrooms plus a bonus room, providing comfortable sleeping arrangements for larger groups. The primary bedroom features a queen bed with an adjoining en suite bathroom, the second bedroom includes a queen and a twin, and the third bedroom offers two queens and two twins. Ideal for kids or multiple families traveling together. The bonus room includes a pull-out couch with a thick memory foam mattress that guests consistently find extremely comfortable.brbrbrbrLarge decks provide space to enjoy fresh mountain air, seasonal views, and quiet evenings under the stars. Sunny Bear is an ideal home base for creating lasting mountain memories.brbrbrbr***Same-Day Bookings: Please contact the host prior to booking to confirm the home has been cleaned and is available.***brbrbrbr***Minimum Booking Age: 24+brbrWe kindly request that no parties take place, and guests must be 24 years of age or older to book the home. Thank you for your cooperation!brbrbrbrGuest Access:brbrGuest has access to whole propertybrbrbrbrThe Neighborhood:brbrWintergreen Resort:brbrbrbrPerched on 11,000 breathtaking acres along the eastern slopes of the Blue Ridge Mountains, Wintergreen Resort is a true four‑season playground. Surrounded by winding trails, cascading streams, and lush forests, it’s the perfect place to unwind, explore, and reconnect with nature. Here you’ll find endless possibilities—whether you’re chasing outdoor adventure, indulging in relaxation, or gathering with family and friends.brbrbrbrIn winter, carve through fresh powder with skiing (steps away from the house), snowboarding, and snow tubing. When the weather warms, tee off on 27 holes of championship golf at the Stoney Creek Course, play on award‑winning tennis courts, hike scenic mountain trails, cast a line fly fishing, or cool off with a refreshing swim. Pamper yourself at the full‑service mountaintop spa, then enjoy a variety of delicious dining options.brbrbrbrWhether you come for the crisp mountain air, the sweeping views, or the countless activities, Wintergreen Resort offers a refreshing escape and unforgettable memories in every season.brbrbrbrGetting Around:brbrNeed transportation or trip planning brbrWe work with a private concierge service that will make your getaway effortless. Offering private transportation, wine and brewery tours, in‑home chefs, spa services, yoga, grocery delivery, and more. They’ll create a personalized experience so you can simply relax and enjoy. Ask host for more info.brbrbrbrOther Things to Note:brbrWintergreen Ski Resort offers 26 runs across 129 skiable acres, vibrant après‑ski dining, night skiing on 45 acres, and Virginia’s largest snow tubing hill—The Plunge brbrbrbrDiscovery Ridge Adventure Center features rock climbing, bungee trampolines, a 25‑ft climbing tower, gem mining, disc golf, 18‑hole mini golf, ninja course, archery, and mechanical bull rides.brbrbrbr✨ Wintergreen Activities (On‑Site & Nearby)brbrbrbrWintergreen Resort Tennis and Pickleball Courts - 2 minbrbrbrbrChestnut Springs Pool (on‑mountain) – 3 minbrbrbrbrWintergreen Spa - 5 minbrbrbrbrWintergreen Ski Resort Base Lodge – 7 minbrbrbrbrThe Plunge Snow Tubing Park – 7 minbrbrbrbrDiscovery Ridge Adventure Center – 7 minbrbrbrbrShamokin Springs Nature Preserve – 8 minbrbrbrbrStoney Creek Golf Course – 21 minbrbrbrbrbrbr Wine & BeerbrbrDevil’s Backbone Brewpub – 15 minbrbrbrbrThree Notch’d Brewing - 20 minbrbrbrbrHill Top Berry Farm & Winery – 20 minbrbrbrbrBold Rock Nellysford Cidery - 20 minbrbrbrbrWood Ridge Farm Brewery – 35 minbrbrbrbrSeven Arrows Brewing Company – 35 minbrbrbrbrBlue Mountain Brewery – 40 minbrbrbrbrVeritas Vineyards & Winery – 40 minbrbrbrbrAfton Mountain Vineyards – 40 minbrbrbrbr Hiking HighlightsbrbrHighlands Leisure Trail – 4 minbrbrbrbrUpper Shamokin Falls Trail – 5 minbrbrbrbrAppalachian Trail Head – 15 minbrbrbrbrBlue Ridge Parkway – 8 minbrbrbrbrThree Ridges Overlook – 10 minbrbrbrbrAppalachian Trail – Three Ridges Hike – 10 minbrbrbrbrCrabtree Falls – 35 minbrbrbrbrbrbr✈️ AirportbrbrCharlottesville–Albemarle Airport – 1 hrbrbrbrbr Water & Pool AccessbrbrChestnut Springs Pool (on‑mountain) – 3 minbrbrbrbrRodes Farm Pool (valley) – 25 minbrbrbrbrLake Monocan (Stoney Creek) – 25 minbrbrbrbrSherando Lake Recreation Area – 30 minbrbrbrbrbrbrWater Activities & Pool AccessbrbrGuests may use the HOA pools at Chestnut Springs (on‑mountain) and Rodes Farm (valley) from Memorial Day weekend through Labor Day. brbrbrbrLake Monocan (20-acre resort lake at 239 Camping Ridge Lane, Stoney Creek) offers swimming, aqua cycles, paddleboards, kayaks, snack bar, and grills; day-use fees please check on Wintergreen Resort Website. brbrbrbrSherando Lake Recreation Area features a scenic 25-acre spring-fed lake with sandy beaches, shaded picnic areas, rustic architecture, and adjacent trailheads. Day-use is $8 per vehicle (up to eight passengers).brbrbrbrImportant Resort Policy Update:brbrAs of newly enacted Wintergreen Resort policy: unaccompanied guests (renters) cannot access the gym, indoor pool, or Devils Knob golf course.brbrbrbrInteraction with Guests:brbrSunny Bear has a wonderful team. We want all our guest to have a 5 star experience. Customer service is important to us. Holly will be your main point of contact for bookings, questions, planning, check-in, and through your stay!

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Bath

Sleeps

$358.21

/ Nightly

Private Vacation Home

Cool Mountain Breezes on The Slopes- It's Pumpkin Spice Time!

Wintergreen Resort, Virginia, United States

Your Wintergreen Resort adventure begins at this marvelous 3-bedroom home with a 2-levels of decks. With 2 king beds, 2 twin bunk beds there is also a full hideaway in the living room. There's plenty of space for everyone. Enjoy the convenience of Wi-Fi, a Hot tub Plus a gas fire pit. Relax in the cozy living room by the fireplace. We hope you'll enjoy your stay at our home. We are only 15 minutes to many breweries and wineries.

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Sleeps

$574.62

/ Nightly

Private Vacation Home

NEW Warren’s Woods! Lovely 5BD, 3BA Wintergreen home. Hot Tub! NEW SPRING RATES!

Wintergreen Resort, Virginia, United States

Wintergreen Resort is waiting for you at this 5-bedroom house. Each room offers an unique sleeping experience, from a king bed to cozy bunk beds. The property boasts a charming living room with a sofa bed for extra guests. Enjoy the soothing atmosphere of the three bathrooms, with two bathtubs and hair dryers. Stay on connected with WiFi and keep warm with heating. Your stay here will be truly enjoyable, surrounded by comfort and convenience. Feel free to reach out to us during your stay - we're happy to suggest local spots to check out.brNo AIR CONDITIONING but generally not needed with windows open and ceiling fans.

Bed

Bath

Sleeps

$384.42

/ Nightly

Private Vacation Home

Mntn View Hot Tub Foosball Fireplace Multi-Deck

Wintergreen Resort, Virginia, United States

4min drive to Wintergreen skiing. Adventure and relaxation await at this mountain top Wintergreen Resort home! With 4 bedrooms and 4.5 bathrooms, this vacation rental offers ideal accommodations for family and friends. Outdoor recreation like skiing and hiking are just around the block, while breweries and vineyards are within 20min drive.brbrSleeps 10brFoosball tablebrTreetop, Seasonal Mountain ViewsbrWood Burning FireplacebrLarge Deck w/ Gas GrillbrRoku TVsbrbrDog fee $150. Seasonal pool/tennis.brThe spacebrPrivate Hot Tub | Multi-Level Deck | 2 Living Areas | 3,000 Sq FtbrbrWhen you want to gather and when you need a little room to breathe, you'll be able to enjoy both at this well-appointed, spacious home, perfect for multi-generational families and a large group of friends!brbrBedroom Suite 1: King Bed, Twin Daybed | Bedroom Suite 2: King Bed | Bedroom 3: King Bed, Twin Bed | Bedroom 4: King BedbrbrOUTDOOR FEATURES: Furnished deck w/ gas grill, screened deck w/ Foosball table, forest views, balcony off of Bedroom Suite 1brbrINDOOR LIVING: Open-concept living area, remote-controlled gas fireplace, 3 en-suite bathrooms, vaulted ceilings, family-style dining table, floor-to-ceiling windows, flat-screen TV w/ cable, den w/ flat-screen TV, 3 bedroom TVsbrbrKITCHEN: Fully equipped w/ breakfast bar, granite counters, stainless steel appliances, knife set, toaster oven, drip coffee maker, Crock-PotbrbrCOMMUNITY: Hiking trails, skiing & other winter sports w/ additional fee, public golfing & swimming at Lake Monacan w/ additional feebrbrGENERAL: Free Wi-Fi, linens/towels, washer/dryer, ceiling fans, hairdryer, high chairbrbrFAQ: $150 Pet fee (paid per-trip)brbrPARKING: Driveway (6 vehicles)brGuest accessbrThe entire home is yours to enjoy!brOther things to notebrWintergreen Ski Resort, Stoney Creek Golf Course, Devils Backbone Brewery and Bold Rock Cidery. Lots of great hiking, horseback riding, mountain biking, lake swimming, skiing, and more. Just ask us for suggestions.

Bed

Bath

Sleeps

$532.66

/ Nightly

Private Vacation Home

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14

Wintergreen Resort, Virginia, United States

Welcome to the Mountain Treehouse! We recently renovated the home with all upgraded amenities, including a brand new hot tub, barrel sauna, fire table outside, and two-sided wood burning fireplace inside. The home is nestled in the tree tops, with oversized windows allowing natural light to fill the space, and has fantastic privacy. Vaulted two story ceilings make the home feel wide open and spacious. New EV charger in the driveway. Plus, pet friendly! Managed by Chris at New School Hosting. (NOTE: video of property was taken before several recent updates, including a deck expansion with addition of hot tub, sauna, and fire table, plus bedroom upgrades)brbrWe are located in the heart of beautiful Wintergreen in Virginia, which has tons to do for all ages, year-round. Mountain Treehouse is just a few minutes’ drive to the slopes and 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), plus there are other great trails just down the street. 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.brbrAdditionally, after a 5 min hike to the base of our property, there is a hiking trail along a creek. In the summer time, supervised kids can play in the creek while adults breathe in the peaceful nature. After heavy rains, you can even hear the rushing waters from the mountain stream at the base of the property. Along that trail is a moderate hike out to Shamokin Falls, Wintergreen's own waterfall!brbrThe house has 4 bedrooms plus loft bedroom, and 3 bathrooms, with the layout as follows:brbrMain level:brbr- Main level deck features outdoor dining for 10, gas grill, rocking chairs, and bar seatingbr- Living room with wood burning fireplace (firewood provided), 65 smart TV, and arcade machinebr- Newly renovated, oversized, and fully stocked kitchen with custom teak root stools surrounding islandbr- Dining area features custom live edge table with seating for 6, plus room for 8 more at the kitchen island (14 seats total)br- BR1: King bedroom with dedicated workspacebr- Full bath with tile showerbrbrLower level:brbr- Lower deck features new hot tub, barrel sauna, fire table (propane provided), and additional outdoor seatingbr- BR2: Master bedroom with king bed and deck access.br- Ensuite bathroom of BR2, fully renovated with double vanity, tiled shower, and soaker tubbr- BR3: King bedroombr- BR4: Bunk room with 3 sets of twin-over-twin beds and built-in reading lightsbr- Jack and Jill full bath: Shared bathroom between BR3 and BR4 with tile showerbr- Laundry room with full size washer and dryerbrbrLoft:brbr- The Loft area is set up as Bedroom 5, but note that it is open to the living room area so not completely private. This room features a queen bed, smart TV, foosball table, and various gamesbrbrOther things to note:brbr- Mountain Treehouse is pet friendly! We allow up to 4 pets with a $100 pet fee (total, not per pet or per night). Also, the deck is entirely enclosed, so unless your pup has a penchant for fence-jumping, they can be outdoors off-leash on the back deck while you enjoy the amenities!br- Wintergreen offers hiking, skiing, snowboarding, tubing, swimming, dining, spa, ropes course, golfing, and much more.br- The driveway is quite long, with a flat parking area near the house. That parking area can fit 3-4 vehicles without any being blocked in. Several more vehicles will fit but will block the others in. There is an EV charger in the driveway.br- Wifi is fast with a strong signal throughout the house and decks.br- We provide a fully stocked coffee bar with multiple coffee drip and Keurig optionsbr- Linens and towels providedbr- 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).br- Pack n play and high chair providedbr- 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.br- 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.

Bed

Bath

Sleeps

$350.61

/ Nightly

Private Vacation Home

Walk to Wintergreen. Hot Tub. Hiking off Property. Cozy 4 BR home.

Wintergreen Resort, Virginia, United States

A four-season wooded retreat offering a cozy getaway for families, friends, girls-weekends, get-togethers, or a couples retreat. Walk to Wintergreen Resort, dining, and slopes. Access hiking trails right off the backyard. Private hot tub on the back deck with nothing but woods behind. Indoors enjoy a cozy den with 70 HDTV, indoor basketball game, mini Pac Man machine, Wii gaming system, games and puzzles. Fast WiFi and AC. Two levels, each with two bedrooms, a bathroom, and living area. Newly renovated bathrooms coming June 2026!brbrMake yourself at home in this traditional mountain-style home with wood-burning fireplace, wood beams and a vaulted ceiling. Enjoy plenty of outdoor space on the two decks (one with a 4-person hot tub) overlooking a private wooded area. With 2 king beds, 1 queen bed, and 1 bunk bed with trundle, there's plenty of space for everyone. (Please note: there are designated sleeping spaces for up to 9, although we allow up to 10 guests to accommodate families with babies/young children). Pack-n-play available. Two separate levels, each with bedrooms, bathroom and separate living areas make it a great choice for multiple families. Enjoy the scenery and relax in the hot tub after a day of skiing or exploring. The property is on a 1/2 acre private, wooded lot with a small creek in the backyard. There are hiking trails adjacent to the property including the 1.7 mile Laurel Ridge Loop and other connecting trails. The cabin offers a private retreat right in the heart of Wintergreen Resort.brbrAccess two private community pools - Chestnut Springs Pool & Rhodes Farm Pool (registration required; guest hours 2pm-close), as well as Lake Monocan in Stoney Creek (closed Tuesdays/Saturdays; entry fee). Schedule a Spa service at WinterGarden Spa and get access to all spa amenities such as pools and sauna.brbrA short walk to Mountain Inn, Wintergreen Resort Ski & Snowboard Slopes, Black Rock Mountain Inn Lodge, WinterGarden Spa, and multiple restaurants. The house located in private cul-de-sac just behind the firehouse. brbrA great getaway in all seasons:brbrSummer: enjoy the pools, visit nearby lake Sherando, playgrounds, hiking, mountain biking, local breweries, wineries & distilleries, hanging out on the decks, or just relaxing in the cool shade of the mountains. Walk to the slopes for live music or to catch the sunset.brbrFall: enjoy the beautiful colors of fall foliage in VA. Drive the Blue Ridge Parkway for spectacular views, go hiking, visit local breweries or wineries. Relax in the outdoor hot tub. Explore a 30-mile network of marked hiking trails, some adjoining the famous Appalachian Trail. Venture out a bit and explore Monticello or Charlottesville. brbrWinter: Enjoy skiing, snowboarding, and tubing at Wintergreen Resort. Walk or 2 minute drive to the slopes. Afterward you can pop back to your own private retreat and relax by a fire with a cup of hot chocolate, soak in the hot tub, or cuddle up and watch a movie. Spend time with friends and family in your own cozy cabin!brbrSpring: Get a head start enjoying the warmer weather. Take the footpath through your backyard, cross the creek, and hop on the trail-head for a hike. Go kayaking in Lake Monocan, learn to fly-fish, or try mountain biking. Explore local eateries. Hike to Crabtree falls. Or just relax with a massage.brbrWintergreen is a four-season resort. Our guests will have access to 2 community pools, Lake Monocan (a 20-acre lake with swimming, paddle boarding and kayaking, a snack bar, and picnic areas; note: lake Monocan is not open to the public on Saturdays/Tuesdays and they do charge an entry fee), and a stocked trout stream. Fly fishing lessons can be booked at Mossy Creek Fly Fishing School. The Discovery Ridge Adventure Center offers rock climbing, an indoor Ninja warrior course, and plunge tubing (winter or summer). Wintergreen hosts a number of events throughout the year including the Blue Ridge Bigfoot Festival, Music Festivals, and Oktoberfest. brbrThe local area has much to offer, including the Blue Ridge Parkway, the Blue Ridge Trail Tunnel (a train tunnel converted to a walking trail), historic sites such as Monticello and University of Virginia (Charlottesville) and Ash Lawn Highland, numerous wineries, breweries, and distilleries (e.g., Veritas, King Family, Pippin Hill, Rebec, Afton Mountain Vineyards, Bold Rock Cidery, Devils Backbone Brewing, and Blue Mountain Brewery), good restaurant options, a creamery, and several nearby orchards. This beautiful part of Virginia offers a scenic, peaceful escape all year round.

Bed

Bath

Sleeps

$814.37

/ Nightly

Private Vacation Home

Mountain Retreat: HotTub, Game Room, Family & Pet-Friendly, 3 King Beds

Wintergreen Resort, Virginia, United States

Welcome to The Wintergreen Cozy!brbrReconnect and unwind in this 5-bed, 3-bath mountain retreat, perfect for large/multiple families or groups and pets. Nestled in nature only 2 minutes from Wintergreen Resort, explore nearby hikes and lakes, wineries & breweries on Hwy 151 for serene days outdoors. brbrEnjoy quiet mornings, and cozy nights by the fire pit. Kids and adults alike will love the jam-packed game room, expansive deck & patio spaces - your haven for family bonding, relaxation and lasting memories. Book today & let nature work its magic!brbrThe spacebrThoughtfully designed to create relaxed, comfortable spaces where your family and friends can come together and reconnect, or find a little quiet time when you need it. With plenty of room to spread out, we comfortably sleep up to 16 guests, making it ideal for large families or groups.brbrHIDDEN GEMS NEARBYbr5 min drivebr- Three Ridges Overlook - breathtaking views of Blue Ridge Mountains, breathe in that mountain airbr- The Plunge Snow Tubing Park -fly down the mountain in a tube and a conveyor belt brings you back up. Open year round.br- Discovery Ridge Adventure Center - Located within Wintergreen Resort, offering ziplining, mini-golf, climbing, and more for families.brbr10-15 mins drivebr- Bold Rock Hard Cider - tasting room and cider garden.br- Rockfish Valley Foundation Natural History Center - nature trails, kids’ programs.brbr20-30 mins drivebr- Nelson 151 is the destination for award-winning Virginia craft beverages including Veritas Vineyard, Afton Mountain Vineyards, Cardinal Point Winery.brbrKEY FEATURESbr- Outdoor fire pit for s’mores and storiesbr- 7-person hot tub to melt the day awaybr- Game room with shuffle board, foosball, arcade, poker table and board gamesbr- Private deck with treetop and mountain viewsbr- Outdoor dining area for fresh air mealsbr- Spacious living areas for gatheringsbr- Fully equipped kitchen for family feastsbr- Large dining table for shared mealsbr- High-speed Wi-Fi for all agesbr- Kid-friendly bunk roombr- Furry friends invitedbr- Smart TVs for movie nightsbr- Quiet reading nooks for relaxationbr- Close to scenic hiking trailsbr- Bedrooms on main floorbr- Washer/dryer for conveniencebr- Ample parking for multiple carsbrbrHOME LAYOUTbr**Upper Level**br- Spacious master suite (Room 1) featuring a king-size canopy bed, a walk-in closet, a 55 smart TV, and a luxurious spa-like bathroom with a soaking tub-perfect for unwinding after a day of adventure.br- Cozy loft area with reading nooks and a dedicated workspace for those who want to catch up on a little work or reading.brbr**Main Level**br- Bright living room with soaring ceilings, comfy seating, and an electric fireplace that invites you to relax and connect.br- Large kitchen equipped with an electric range, full-sized refrigerator, and a brand-new dishwasher. It’s fully stocked with stainless steel pots and a beautiful stoneware dinner set - everything you need to create delicious meals for your whole crew.br- Enjoy two coffee stations for cozy mornings: br1) Complete with Keurig coffee machine and Keurig pods, creamer, sugar and tea. br2) And a pour-over coffee maker with stainless steel filter, syrup and complimentary ground coffee. Feel free to bring your own ground coffee if you want.br- Dining area with seating for 10–12, ideal for family dinners or game nights.br- Bedroom 2: King bed with serene forest viewsbr- Bedroom 3: Two queen bedsbr- Expansive deck featuring a BBQ grill, patio dining for 12, bar seating, and a lounging sectional with a fire pit - don’t miss the stunning sunsets from here!br- Fully stocked bathroom on this level for your convenience.brbr**Lower Level**br- Fun-filled game room with shuffleboard, foosball, poker table with chips, record player, arcade games, board games, books and a 55 smart TV - hours of entertainment for all ages!br- Brand-new paved patio “garden room” with a 7-person hot tub, large hammock for two (perfect for afternoon naps), and cozy seating to relax the day away.br- Bedroom 4: King bed with garden viewsbr- Bedroom 5: Two twin-over-full bunk beds that sleep 6 kids comfortably, complete with mini basketball hoop, Connect 4, and a play tent to keep the little ones happily entertained.br- Laundry room with washer, dryer, detergent, and dryer balls for your convenience.br- Fully stocked bathroom on this level as well.br- Mudroom with side access to the property for easy comings and goings.brbrComfort & ConveniencebrAll bedrooms feature comfy memory foam hybrid mattresses, blinds, and blackout curtains to ensure a restful night’s sleep.brbrBathrooms come stocked with soft towels, facial tissues, body wash, shampoo, and conditioner - just bring yourself and your favorite pajamas!brbrWe can’t wait to welcome you to your home-away-from-home in the mountains. If you have any questions or special requests, just let us know - we’re here to help make your stay unforgettable!brbrGuest accessbrEnjoy the entire house, it is exclusively for your enjoyment.brbrThe address, door code, and other essential info will be sent 3 days prior to your check in date.brbrCheck in: Any time after 4pm ESTbrCheck out: 10am ESTbrbrUp to 4-5 cars can be parked on the driveway. close to the front door. Please no RVs, campers or trailers. Wintergreen roads are paved, often windy, and with some inclines. In winter, we recommend a four-wheel drive vehicle.brbrOther things to notebrA Few Steps to AdventurebrThere are 6 steps from the driveway up to the front door. For anyone in your group who prefers to avoid stairs, we have a spacious king bedroom and a double queen bedroom on the main level-no need to climb! Please note, the upper and lower (basement) floors are only accessible by stairs, which may be a bit steep for some.brbrStay ConnectedbrEnjoy fast, reliable WiFi with a strong signal throughout the house - perfect for streaming, remote work, or keeping the kids entertained.brbrAll the EssentialsbrWe provide fresh linens and towels for your stay, so you can pack light!brbrWildlife & Trashbr- You’re in the heart of nature - black bears, deer, and raccoons are frequent visitors! br- **IMPORTANT** For your safety, never leave food or trash outside - this includes used glasses, cups, plates, etc. Wildlife loves a snack, but we want to keep them (and you!) safe.br- Please take your trash to the nearby compactor: just enter “Blackrock Dr & Tyro Ln, Wintergreen Resort, VA 22967” into Google Maps - it’s a quick 3-minute drive and the compactor will be on your left. If the trash is left at the property, extra cleaning fees may apply. Thank you so much for helping us keep the area clean!brbrReady for Family MealsbrThe kitchen is stocked with basics like cooking oil, salt, and pepper - just bring your favorite ingredients and you’re all set.brbrLittle Ones WelcomebrTraveling with babies or toddlers We’ve got you covered with baby gates, a high chair, pack & play and lightweight, unbreakable dinnerware set for your convenience.brbrFurry Friends InvitedbrWe love pets! Bring up to 2 pets for $100 per pet per stay. We’ve made it easy for pet parents by providing a Coolaroo bed, bowls, and towels for any little messes. Just a gentle reminder to pick up after your pets.brbrSimple ParkingbrThere’s plenty of parking on the driveway for your group. Please note that Wintergreen HOA doesn’t allow street parking.brbrSummer Fun at the PoolbrYou’ll have free access to the community pool during the summer months! The HOA allows up to 6 guests at a time, and pool hours are 2–6pm - perfect for an afternoon splash. Send me a message if you'd like to arrange.

Bed

Bath

Sleeps

$638.5

/ Nightly

Private Vacation Home

Little Bear: 4br/ 4ba, mountain & valley view. Pet friendly!

Wintergreen Resort, Virginia, United States

Welcome to Little Bear! We'd love to provide you with a comfortable stay and clear views so you can enjoy the beauty of the Blue Ridge Mountains!brAt 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.

Bed

Bath

Sleeps

$536.57

/ Nightly

Private Vacation Home

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

Wintergreen Resort, Virginia, United States

8min walk or 3min drive to ski. Sweeping views year round. Retreats, romantic weekends or adventurous getaways. Close to wineries, breweries, farmers market, and walking distance to three great hiking trails.brbrSleeps 16: K, K, Q, 2x Double + 4 Twin (Bunk beds), 1 Pull out sofa bed in Living Rmbr★Dogs OKbr★2,714sqftbr★HOT TUB for 7br★Sound systembr★2-Story vaulted ceiling, gas fireplace, 60TVbr★Dining table for 6 + breakfast barbr★Workspace w/ FAST Wi-Fibr★Shuffleboardbr★Pool tablebrbrSeasonal pool/tennis. Resort access not included. Pet fee $150.

Bed

Bath

Sleeps

$1525.35

/ Nightly

Private Vacation Home

Heaven On Earth ~ Wintergreen Mountain

Wintergreen Resort, Virginia, United States

Nestled amid the pristine beauty of the towering mountains, Heaven On Earth provides the perfect alpine escape for those seeking tranquility and adventure. Whether you`re an avid skier or simply seeking a serene mountain retreat, this home provides an unforgettable experience in the heart of the Wintergreen resort. After a day on the ski slopes, unwind by the crackling fireplace or soak in the private hot tub on the outdoor deck, surrounded by the crisp mountain air!brbrTop of Wintergreen! Heaven on Earth is perched near the highest point at Wintergreen Resort. With unsurpassed sunrise and sunset views of the south and western Blue Ridge, this is truly one of the most spectacular mountain homes you will find anywhere! From the moment you enter you are struck by the panoramic view perfectly framed by the floor to ceiling windows and the overwhelming quality, craftsmanship and luxury of the post and beam style great room. brbrAn architectural gem, this home’s open floor plan flows from the massive great room to the dream chef’s kitchen, with dining for 18+ and is highlighted by the massive double-sided fireplace that connects the cozy living room, library and game room. Walk out to the expansive, multi-level deck with a private, oversized 8-person hot tub, and you will enjoy from the privacy of your own home the same breathtaking views that people come from far and wide to enjoy at the Devils Knob Overlook, just 500 feet down the street. The Overlook is a popular place for outdoor weddings because of the stunning backdrop, and this home makes a wonderful place for bridal party preparations and photos.brbrPerfect for a multi-generational family escape, this home features a main-level king-suite and two more primary suites on the second floor, all with amazing views, oversized windows and spa baths. In addition, there are two bunk rooms, each with their own private full bath, a twin-over-double bunk bed and futon. The second floor bedrooms are arranged around an upstairs den with floor to ceiling windows, perfect for another gathering area. Finally, the third level loft is a kid’s dream with four twin beds surrounding a game center.

Bed

Bath

Sleeps

$689.11

/ Nightly

Private Vacation Home

Blue Ridge Mountain Retreat in Wintergreen

Wintergreen Resort, Virginia, United States

Welcome to Blue Ridge Mountain Retreat at Wintergreen! This amazing property is the newest addition to Wind Luxury Properties and joins our properties at Smith Mountain Lake (VRBO #'s 648334, 515931, 825368) and our amazing home on the Rappahannock River (VRBO #966039), giving our guests the opportunity to enjoy the high end properties we offer at a 4 season mountain top resort offering winter snowsports! We specialize in providing the high quality accommodations you desire to build lasting vacation memories with your friends and family!brbrBlue Ridge Mountain Retreat at Wintergreen was acquired in November of 2017. It was previously rented through Wintergreen as Time Away and was one of the top 3 properties at the entire resort for the last 5 years. However, if you rented it previously, it will look quite different--in a GREAT way! The property was not up to our standards and immediately after purchase we embarked on a face lift for the home with new furnishings, games, kitchen appliances, pillows, linens, etc.We are dedicated to providing our guests with abundant amenities, comfort, and luxury at all of our properties, no matter what the costs!brbrThis home is an amazing 4800 square foot luxury home located just a short distance from Mountain Inn, ski areas, Founders Vision Overlook, Devil's Knob Golf Course, Tennis Center, Spa, and Fitness Center. We provide you with 7 spacious bedrooms and 4.5 baths, 2 of which are master suites and include a jetted tub in addition to showers. We are able to sleep 20 guests in beds. There are also 4 wood burning fireplaces with firewood provided to roast marshmallows, keep you warm, and provide the crackle by the fire you desire while in bed or on the sofa during cold winter nights. Our luxury kitchen is fully stocked with everything you need for Thanksgiving or Christmas dinner, or a feast after a long day on the ski slopes, tennis courts, golf course, or hiking through the mountains. Cook in style with granite countertops and stainless steel appliances prior to enjoying the fruits of your labor at our large dining room table, which seats 12 directly adjacent to the bar which can accommodate another 5 hungry guests! When you have had your fill of the outdoors, you can still enjoy your vacation inside with high speed internet, cable TV, a wide selection of DVDs, card and board games, as well as ping pong and foosball tables.brbrWintergreen Resort is a 4 season mountain resort located in the beautiful Blue Ridge Mountains. You are less than an hour from Charlottesville, home of UVA, Thomas Jefferson's Monticello, and the amazing 33 member Monticello Wine Trail, as well as an hour from the city of Lynchburg. The famous Blue Ridge Parkway passes beside Wintergreen offering opportunities for scenic drives, hiking, and year round escapes. Wintergreen itself is a massive 10,000 acre tract of land with ski slopes, snow tubing, golf courses, restaurants, stores, tennis and meeting facilities, as well as absolutely breathtaking views--just google Founders Vision Overlook at Wintergreen or Blue Ridge Overlook on Devil's Knob for examples. The resort offers 25 ski and snowboard slopes, Ridgely's Fun Park for kids, The Plunge 12 lane snowtubing, 45 holes of championship golf, 22 tennis courts, and a full service spa. The resort in located in Nelson County, near the small town of Nellysford. Within just a couple miles, you can be at several award winning wineries as well as a who's who list of famous Virginia microbreweries!br brWe welcome any questions and hope you will allow us to help provide you and your family with vacation memories you will cherish forever!brbrFor your safety, we have security Sytems at all of our homes which some homes inlaced outdoor security cameras.br

Bed

Bath

Sleeps

$598.93

/ Nightly

Private Vacation Home

3 Bedroom Chalet on Eagles Swoop ski slope

Wintergreen Resort, Virginia, United States

Step onto the slopes from this cozy mountain house this winter! A true ski in/ski out mountain home just steps to Eagle Swoop. The perfect spot to celebrate the holidays with your family. The house is secluded at the end of Pinnacle Drive and walking distance to slopes, the Mountain Inn, shops and dining. 3 BR, 2 BA house with a woodstove and plenty of firewood, flatscreen tvs in every room, washer/dryer, deck with grill and ample parking. 1 King bed, 1 Queen bed, 2 sets of Bunk beds and fold out futon in the cozy upstairs loft great for kids. Enjoy watching the skiers from dining table and sitting around the fire.

3

Bed

8

Sleeps

Exceptional(18)

$266.49

/ Nightly

Private Vacation Home

Hot Tub Pool Pac Man Foosball Dogs OK Tennis Golf

Wintergreen Resort, Virginia, United States

4min to ski, walk to trails! Endless activities: apple picking, breweries/wineries, hiking, lake, horseback, golf, tennis, skiing Take a peaceful morning walk on path across the street from the cabin. One mile to Founder's Overlook and amazing sunrises!brbr★Hot tub w/ forest viewbr★Foosball, PAC-MANbr★Comfortably sleeps 9: K, Q, Q, Double +Twinbr★Great Room w/ fireplacebr★FAST Wi-Fibr★5 Smart TVsbr★High-end mattressesbr★Pack 'n play and HighchairbrbrHappy dog fee $187. Outdoor pool/tennis access included.brPlease note the indoor fireplace is purely ornamental.

4

Bed

3

Bath

9

Sleeps

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