Vacation Rentals By Owner In Wintergreen Resort, VA

Wake up above the treetops in this beautifully updated top-floor condo at Wintergreen Resort — Virginia’s premier four-season mountain destination. Whether you’re here for skiing, hiking, or simply doing nothing at all, this stylish retreat has everything you need to unplug and recharge.brbrThe open living area features a cozy gas fireplace, a leather sofa, and a one-of-a-kind foosball coffee table — perfect for groups and families. Step directly onto the private balcony with string lights and a full sectional sofa, overlooking peaceful mountain greenery. The dining nook seats four around a gorgeous walnut table beneath a brass pendant light, wrapped by windows on three sides with treetop views. The fully equipped kitchen has granite counters, stainless steel appliances, a shiplap backsplash, and a full coffee station — everything you need for a cozy night in after a day on the mountain.brbrThe primary suite features a queen bed, vaulted ceilings, and an en-suite bath with a tub/shower combo. The second bedroom is a mountain-themed retreat with a queen bed and a twin trundle — ideal for kids or extra guests — with a full bath conveniently across the hall. The space comfortably sleeps 6.brbrWintergreen Resort has something for every season. Ski and snowboard in winter, hike over 30 miles of trails in summer, and enjoy access to two resort pools when the weather warms. The Wintergreen Spa is just steps away, and the resort’s restaurants and golf course are all within easy reach. Free parking is right in front of the building.brbrPets are welcome! We’re hands-on hosts — a teacher and her husband — who are always just a message away. The entire condo is yours; we keep just one small closet locked for storage. Self check-in via smartlock.

Treetop Mountain Escape - Fireplace, Views & Pool

Wintergreen Resort, Virginia, United States

2

Bed

2

Bath

Exceptional(2)

$160.29

Escape to the mountains and relax in this cozy 1-bedroom Wintergreen condo located in the heart of Wintergreen Resort. Perfect for couples or solo travelers, the condo offers a peaceful retreat just minutes from skiing, hiking, wineries, breweries, golf, and the Blue Ridge Parkway.brbrThe bedroom features a comfortable queen bed, while the living room includes a sleeper sofa, smart TV, fireplace, and large windows that bring in the mountain atmosphere. Step outside onto the private deck with gliders and enjoy fresh mountain air, sunset views, and the quiet wooded setting.brbrThe kitchen is fully stocked with cookware, dishes, coffee maker, microwave, stove, refrigerator, and essentials for preparing meals during your stay. The condo also includes high-speed WiFi, streaming TVs, heating and air conditioning, fresh linens, towels, hair dryer, and convenient self check-in with smart lock access.brbrGuests can walk to nearby resort amenities, restaurants, the market, and seasonal activities. Whether you're here for ski season, hiking the Blue Ridge trails, winery weekends, fall colors, or simply a quiet mountain escape, this condo is a comfortable home base for exploring everything Wintergreen and Nelson County have to offer.brbrCome relax, recharge, and enjoy the beauty of the Blue Ridge Mountains.

Walk to Slopes and Restaurants - Cozy 1 Bedroom Condo

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$814.37

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.

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

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$638.5

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.

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

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$536.57

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.

Hot Tub Pool Table Dog OK Tennis Golf Shuffleboard

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$1525.35

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.

Heaven On Earth ~ Wintergreen Mountain

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$689.11

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

Blue Ridge Mountain Retreat in Wintergreen

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$421.13

A Mountain home nestled in the Blue Ridge Mountains with breathtaking valley views and mesmerizing sunrises! The property is on a quiet cul-de-sac that is conveniently located close to Wintergreen's main resort village. Perfect for the family seeking a tranquil escape and a love of nature. Sit back and enjoy the majestic views on the wrap around deck, relax in the hot tub or gather around one of the stone fireplaces inside after a day of fun activities.

Cabin

Wren Time, Wintergreen Mountain Retreat with Hot Tub

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$598.93

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 Bedroom Chalet on Eagles Swoop ski slope

Wintergreen Resort, Virginia, United States

3

Bed

8

Sleeps

Exceptional(18)

$266.49

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.

Hot Tub Pool Pac Man Foosball Dogs OK Tennis Golf

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$238.79

Plucked from a German fairytale, this thoughtfully-designed oasis features intricate wainscoting and slate floors. Senses will be amazed with the attention to detail at each turn as you warm yourself at a wood-burning fireplace, a focal point of our living room, or have a fireside chat at the outdoor gas fire pit on the veranda. Family and fur-friendly, so bring the kids and pup.brbrSleeps 8: Q, full, 2x twin, Q sofa bed, pack 'n playbrFire pitbrbrHappy dog $150. Outdoor pool/tennis access in season

Chalet

Hansel 'n Gretel: Wood Stove Grill Firepit Dogs OK

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$414.67

Welcome to The Brown Bear Lodge, your year-round retreat in the heart of Wintergreen Ski Resort- just a short walk from the main chair lift Mountain Inn Resort with many restaurant options. Unwind by the original stone fireplace after a fun filled day soaking in the crisp mountain air. With updated decor, the interior offers the perfect cozy and comfortable setting to feeling right at home for visitors seeking a place to rest after a day of adventure in the Blue Ridge Mountains. Enjoy seasonal mountain views from the balcony enjoying the conversations by the outdoor fire pit as well as the ability to explore nearby hiking trails and charming wineries, breweries, cideries & distilleries... just minutes away along Nelson's renowned 151. Wintergreen is a unique destination boasting a variety of activities during each season such as skiing, tubing, hiking, biking, fishing, boating, tennis, swimming, fitness, golf, and rejuvenating spa opportunities. Let's not forget about the many dining options just moments from our home- it is a culinary experience that will have you coming back for more! The Brown Bear Lodge is a 3 bedroom 2.5 bath standalone home tucked back at the end of a cul-de-sac where you can enjoy the peacefulness of being away from the city. The space will accommodate two families ideally -with a bunk bed room to comfortably sleep 4 children and two separate accommodations with luxury memory foam queen size mattresses for a good night's sleep. Each bedroom is equipped with a closet to neatly hang clothing (hangers provided), and a sound machine. Very family friendly where the loft is stocked with games, cards, music, toys, bean bag chairs and a Big Buck Hunter arcade. The space comes with all basic amenities you will need including drip coffee machine, propane grill on the deck, a fully equipped kitchen with a slow cooker, air fryer, toaster, and blender. Spices, sugar, pots and pans, utensils, dishes, wine glasses, bourbon glasses, wine and bottle opener, linens, towels, and hair dryers are all included. If you have any questions about items provided, please feel free to reach out. We will be happy to assist and reply within an hour! Your mountain adventure begins here, at The Brown Bear Lodge, to experience the ultimate retreat in the heart of nature!

Cozy Wintergreen Ski Chalet -hot tub-Walk to slopes & family friendly!

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$223.27

Summary:brbrBear Paw is a newly renovated, pet friendly two bedroom, two bath condo located in the Three Ridges community at Wintergreen Resort. One of the most walkable areas on the mountain, it is just a short stroll to the Village, where you will find restaurants, ski check in, shops, and the Mountain Inn.brbrbrbrWhether you are visiting for skiing, hiking, golf, or a peaceful getaway with your four legged companion, this inviting retreat offers the perfect base camp for every season.brbrbrbrThe Space:brbrBear Paw is perfectly situated in one of Wintergreen’s most connected locations. Step right out your door to access the Highlands Leisure Trail, or enjoy a short walk to the Village hub, home to the Mountain Inn, The Edge, Copper Mine Restaurant, Upper Crust Pizza, The Market, ski check in, and Discovery Ridge Adventure Center. On weekends and holidays, the free resort shuttle stops nearby, making it easy to explore without ever needing your car.brbrbrbrThis radiant end-unit condo is designed for both comfort and convenience, featuring vaulted ceilings and an abundance of windows that fill the space with natural light.brbrbrbrThe comfortable living area invites you to relax by the wood-burning fireplace with a beautiful brick surround (firewood provided), perfect after a day on the slopes or trails. The updated kitchen offers granite countertops and newer appliances, while luxury vinyl plank flooring throughout (no carpet!) adds a clean, modern touch.brbrbrbrStep outside onto your private deck overlooking the peaceful woods. An ideal spot for morning coffee or unwinding in the evening.brbrbrbrPets are welcome at Bear Paw, we love your four legged family members! Well behaved dogs are invited with no breed restrictions. Step right outside to the Highlands Leisure Trail for easy morning walks, or explore the surrounding woods full of new scents and adventure. A pet fee of $75 per stay applies, with a maximum of 2 pets, please disclose at booking.brbrbrbrYou’re just a short walk to The Village and Highland Leisure Trail, placing you right in the heart of everything Wintergreen has to offer.brbrbrbrFrom snowy ski days to summer hikes, vibrant fall foliage, and fresh spring escapes; Bear Paw is your perfect four-season mountain retreat!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: 21+brbrWe kindly request that no parties take place, and guests must be 21 years of age or older to book the home. Thank you for your cooperation!brbrbrbrGuest Access:brbrGuest has access to whole property.brbrbrbrThe Neighborhood:brbrBear Paw is ideally located in the heart of Wintergreen’s mountaintop community, just a short walk to Blackrock Village, the center of resort life. Here you will find local favorites like The Edge, Copper Mine, and Upper Crust Pizza, along with The Market for groceries and grab and go meals, the Mountain Inn, ski check in, and Discovery Ridge Adventure Center. The Highlands Leisure Trail winds through beautiful old growth forest right from the neighborhood, perfect for a peaceful hike. On weekends, the free resort shuttle makes it easy to explore the mountain without a car. Just a short 15 to 20 minute drive down the mountain brings you to Devil’s Backbone Brewpub and Bold Rock Cidery for even more local flavor.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 Ski Resort Base Lodge – walking distancebrbrbrbrWintergreen Spa - 4 minbrbrbrbrThe Plunge Snow Tubing Park – 4 minbrbrbrbrDiscovery Ridge Adventure Center – 4 minbrbrbrbrWintergreen Resort Indoor and Outdoor Tennis and Pickleball Courts - 4 min (small fee to play)brbrbrbrShamokin Springs Nature Preserve – 6 minbrbrbrbrChestnut Springs Pool (on‑mountain) – 6 minbrbrbrbrStoney Creek Golf Course – 19 minbrbrbrbrbrbr Hiking HighlightsbrbrbrbrHighlands Leisure Trail – walking distance brbrbrbrBlue Ridge Parkway – 9 minbrbrbrbrThree Ridges Overlook – 9 minbrbrbrbrReid’s Gap Trailhead AT – 9 minbrbrbrbrUpper Shamokin Falls Trail – 10 minbrbrbrbrAppalachian Trail Head – 15 minbrbrbrbrCrabtree Falls – 35 minbrbrbrbrbrbr✈️ AirportbrbrCharlottesville–Albemarle Airport – 1 hrbrbrbrbr Water & Pool AccessbrbrChestnut Springs Pool (on‑mountain) – 6 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:brbrBear Paw 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!

Pet-Friendly Retreat | Walk to Slopes & Village!

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$167.58

Walk to Wintergreen Conference Center | Near Hiking Trails | Community Pool AccessbrbrExperience the best of the mountains at this Wintergreen vacation rental! This inviting condo offers a prime location within walking distance of the Wintergreen Conference Center, making it the perfect base for events and outdoor adventures. Spend your days exploring nearby hiking trails or visiting the Market before returning home to relax by the pool. Your mountain escape awaits—book today!brbr-- THE PROPERTY --brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 king bedbr- Bedroom 2: 1 queen bedbr- Living Room: 1 queen sleeper sofabrbrLAURELWOOD CONDOS AMENITIESbr- Seasonal outdoor pool (opens early June)br- Complimentary firewoodbrbrKITCHENbr- Stove/oven, refrigerator, microwave, dishwasherbr- Drip coffee maker (bring your own coffee)br- Blender, toasterbr- Cooking basics, trash bags/paper towels, dishware & flatwarebrbrINDOOR LIVINGbr- Smart TV, wood-burning fireplacebr- Dining tablebrbrOUTDOOR LIVINGbr- Patio, bistro tablebr- Pool viewsbrbrGENERALbr- Central heating & A/Cbr- Washer/dryer, iron/boardbr- Linens/towels, complimentary toiletries, hair dryerbr- Free WiFibr- Keyless entrybrbrFAQbr- 1 exterior security camera (facing out)brbrACCESSIBILITYbr- Single-story condo, exterior stairs to accessbrbrPARKINGbr- Community lot (2 vehicles)brbr-- THE LOCATION --brbr- Centrally located near hiking trails & ski slopesbr- Access to on-site dining, kids' snowboard/ski programs, & panoramic viewing platformbr- 0.4 miles to Discovery Ridge Adventure Center, The Plunge Snow Tubing Park, & Wintergreen Adaptive Sportsbr- 3 miles to Shamokin Springs Nature Preservebr- 7 miles to Ravens Roost Overlookbr- 8 miles to Sherando Lakebr- 28 miles to Frontier Culture Museumbr- 33 miles to Grand Cavernsbr- 48 miles to Charlottesville–Albemarle Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- No outdoor fires or grillingbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story condo requires exterior stairs to accessbr- The seasonal outdoor pool will open early Junebr- Your safety matters. This property features 1 exterior camera at the front door facing the front outdoor entry. The camera does not look into any interior spaces. The camera records video and sound when activated by motion

Wintergreen Condo w/ Pool: Near Hike & Market!

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$557.0

Bring the whole family to this warm mountain home! Welcome to Whitetail Lodge, a well designed home in the heart of Wintergreen. A perfect spot for groups or families, tons of games, record player, kids teepee tent area, two fire pits, lots of areas to spread out, and multiple outdoor seating areas. With 5 bedrooms total, a full loft, plus a downstairs living room, bunk room, and game room! There`s plenty of room for up to 14 guests and it is pet friendly!brbrThe house is about a 3 minute drive to the slopes, dining, and everything else Wintergreen has to offer. There`s also a fantastic hiking trail a walk away and the Shamokin Springs Nature Preserve is across the street. The Devils Knob Overlook is just 1.5 miles and the Upper Shamokin Falls Trail is just up on the ridge. Some of the best hiking trails in the state are off the Blue Ridge Parkway (15 minutes from the house), two sandy beach entrance lakes plus a community pool for swimming, and over dozen wineries, breweries, and distilleries within a 30 minute drive.brbrThe home is practically laid out for many guests to enjoy at once without feeling cramped! The layout is as follows:brbrLower level:br- Living room with access to lower deck and hot tub stocked with games and puzzlesbr- Bedroom 1: 2 twin beds, smart TVbr- Bedroom 2: Twin over queen bunk bed with an additional twin bed, smart TV, puzzles, games,brtoys and books, bean bag chairsbr- Game room with foosball, arcade games, darts, basketball, smart TV and small barbr- Full bathroom in the hallwaybr- Brand new deck with hot tub, string lights and Bluetooth speakersbr- Nightlight in the hallwaybr- Air purifier and in-wall dehumidifierbr- Outside of the lower level is a ski closet so you don’t have to bring your wet ski gear in the housebrbrMain living level:br- Living room with ample seating with gas fireplace and large smart TVbr- Access to the upper deck with seating, gas firepit and propane gas grillbr- Fully stocked kitchen including crock pot, Keurig and coffee pot stocked with coffee pods, sugar, and creamerbr- Dog necessities like dog bowl and waste bagsbr- Bar seating at the kitchen counterbr- Dining areabr- Full washer and dryerbr- Full bathroom in the hallway with a bathtubbr- Bedroom 3: King bed with smart TVbr- Bedroom 4: Queen bed with smart TVbr- Nightlight in the hallwaybrbrUpper Level:br- Loft with record player and recordsbr- Kids teepee play area with play smores kit and faux fire logsbr- The most comfortable reading chair ever is located in the loft which comes stocked with booksbr- Pull out sofa that sleeps 2 comfortablybr- Bedroom 5: King bedroom with Smart TV and a small deck off the back with seating for 2br- Nightlight in the hallwaybr- Full bathroom in the hallwaybrbrGuests have access to the entire home.brbrYou will be provided a door code which will work for both entrances. A second-floor entrance to the main living area, and a ground-level entrance with outdoor storage and a mudroom area for all of your ski or hiking gear.brbrWe message all of our guests via the hosting platform, but we are also available anytime by phone or text.brWe allow a max of 2 dogs. Please make sure you include pets on the booking.

Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$574.76

Escape to our spacious 3-bed, 3-bath mountain condo, perfect for families or groups. Enjoy cozy evenings by the gas fireplace, a fully equipped kitchen, and a private patio with a grill. With 3 king beds, everyone has a comfortable retreat. Located on the 18th fairway, you're moments from world-class skiing, hiking, and championship golf. Your year-round adventure starts here!brbrThe spacebrStep into a warm and welcoming mountain retreat. The open-concept living space is perfect for relaxing and socializing after a day of adventure.brbr**Living Area:** br* Large sectional sofa invites you to relax by the cozy gas fireplace. br* Smart TV for your entertainment needs. br* Large windows fill the room with natural light and offer peaceful views of the 18th fairway. brbr**Kitchen & Dining:** br* Modern, fully equipped kitchen with stainless steel appliances. br* All necessary cookware, dishes, and utensils provided. br* Spacious dining table perfect for sharing meals or enjoying a game night. brbr**Bedrooms & Bathrooms:** br* Primary Bedroom: King bed with a private ensuite bathroom. br* Bedroom 2: King bed with a private ensuite bathroom. br* Bedroom 3: King bed with easy access to a modern, updated full bathroom. br* All 3 full bathrooms are stocked with fresh towels and essential toiletries. brbr**Outdoor Space:** br* Private walk-out patio with outdoor seating to enjoy the fresh mountain air while you overlook the 18th fairway through the trees.br* Electric grill available for your use.brbrGuest accessbrGuests will have private and exclusive access to the entire 3-bedroom, 3-bathroom condo. This includes the living room, fully equipped kitchen, all bedrooms, and the private walk-out patio with a grill. brbrCheck-in is seamless and contact-free via a keyless entry system. You will receive your unique, private door code through the app prior to your arrival for easy self-check-in at your convenience.brbrThe neighborhoodbrDiscover the charm of Wintergreen Resort, your perfect base for a Blue Ridge Mountain adventure! brbrOur condominium is nestled in a tranquil neighborhood, ideal for families and nature enthusiasts. You'll find yourself surrounded by lush forests, scenic overlooks, and miles of hiking trails, perfect for morning walks or evening stargazing. brbrEnjoy direct access to year-round activities like skiing, snowboarding, golf, and tennis with a free resort shuttle. brbrJust a short drive away, explore award-winning wineries and savor farm-to-table dining in Nelson County. brbrThis family-friendly neighborhood offers a blend of adventure and relaxation, making it a welcoming retreat for all.

Spacious 3BR 3BA Pet Friendly Resort Condo

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$458.95

Top of the Mountain! Enjoy a view of the slopes and a backdrop view of many miles beyond that. You will want to wake up early to take in the sunrise! Flat driveway with only a couple steps to get inside allows guests with somewhat limited mobility to have easy access to the home and to the main floor which features a primary suite, queen bedroom, kitchen, laundry room and guest bathroom. Relax on the deck, in the hot tub or the screened porch. All of which have spectacular views!

Ridge Retreat @ Wintergreen!

Wintergreen Resort, Virginia, United States

4

Bath

10

Sleeps

Exceptional(18)

$363.08

Drive up Fox Sparrow Lane through a tunnel of Blue Ridge trees, and the cabin appears between the pines. Inside: soaring ceilings, a wood-burning fireplace, and a jaw-dropping two-story Blue Ridge Mountain mural, a completely original commission hand-painted by a local Virginia artist specifically for this home. Outside: a private hot tub and sauna under a canopy of stars. This is where the week’s noise stays in the car.brbrTHE GREAT ROOM — AND THE MURALbrThe centerpiece of the cabin is a show-stopping custom two-story Blue Ridge Mountain mural, a completely original work commissioned specifically for this space and hand-painted by a local Virginia artist. It spans the full height of the great room wall and is the first thing guests photograph when they walk through the door. You will not find this mural anywhere else. Vaulted ceilings, a stone wood-burning fireplace stacked and ready, a chef’s kitchen with a quartz island that seats four, and a dining table for eight surround it. Floor-to-ceiling windows pour the forest inside. A window nook with leather chairs is where someone always ends up with a book and a coffee.brbrTHE SPACEbr3 bedrooms · 2 bathrooms · Sleeps 7brPrimary Suite (King + twin sleeper chair): En-suite bathroom, ceiling fan, Smart TV, and a private slider that opens directly to the back deck — the hot tub and sauna are six steps from your pillow.brBedroom 2 (Queen): Rustic headboard, forest views from the window, its own TV, and ceiling fan.brBedroom 3 — Bunk Room (Double + Twin): The kid magnet. Patio access, a retro Ms. Pac-Man arcade nook, and bunks that sleep three.brThe Kitchen: Brand-new sage cabinets, quartz island, stainless appliances, and real cooking gear — pots, pans, sharp knives, spices, coffee maker, blender, toaster, wine glasses for the whole crew.brbrOUTDOOR AMENITIESbrPrivate hot tub and sauna tucked under the trees. Fire pit ringed with seating and café string lights. Blackstone griddle for group breakfasts. Second fire-table on the upper deck. Disc golf hole right on the property. Multi-level deck wrapped in string lights.brbrTHE SCREENED GAME PORCHbrScreened, covered, built for rainy afternoons — ping pong, foosball, dartboard, and a giant Connect 4 that disappears entire evenings. No other property in this neighborhood has a dedicated enclosed game porch.brbrLOCATIONbrYou’re inside Wintergreen Resort — 11,000 acres of Blue Ridge Mountain on Virginia’s Route 151 wine and brew trail. Shamokin Springs Loop Trail is steps from the back door.brOn the resort (5–10 min):br• Ski slopes and snow tubing (winter)br• Resort pool (complimentary access 2–6pm, up to 6 guests per HOA rules)br• Full-service spa and Mountain Inn restaurantbrWineries & breweries on Route 151:br• Devils Backbone Basecamp Brewpub, Bold Rock Cidery, Three Notch'd Brewer, Blue Toad Hard Cider ~20 min · Veritas Vineyards, Afton Mountain Vineyards ~30 min · Blue Mountain Brewery, Hazy Mountain Brewery 25–35 minbrHiking:br• Blue Ridge Tunnel Hike ~30 min • Crabtree Falls (Virginia’s tallest cascading waterfall) ~40 min · Blue Ridge Parkway (Reeds Gap, MP 13.6) 10 min · Sherando Lake Recreation Area ~25 minbrDay trips: Charlottesville & Monticello ~45 min · Staunton ~45 min · Natural Bridge State Park ~1 hr 30 minbrbrWHO THIS HOME IS BEST FORbrFamilies with kids: Bunk room, screened game porch, high chair, crib, and disc golf hole right on-site.brCouples celebrating: Six steps from the king bed to a private hot tub. Sauna for two. The custom mural as the backdrop for every morning.brFriend groups — ski or hike weekend: Three bedrooms, sleeps 7, giant great room, screened game porch, and a mural that makes every breakfast feel like a moment.brRemote workers needing a reset: Fast WiFi, peaceful forest setting, hiking at the door. Take the morning call under the mural, then disappear into the woods.brbrGOOD TO KNOWbr• Self check-in via private keypad code sent the day before arrivalbr• No air conditioning — ceiling fans throughout; Blue Ridge nights are cool (55–65°F even in summer)br• Bear-aware setting: keep food and trash inside — we provide bear bins and remind you in pre-arrival messagesbr• Exterior security cameras at driveway and lower back deck (no interior cameras)br• Level 2 EV charger on-site (bring your own plug adapter)br• Pet-friendly: up to 2 dogs under 50 lbs | $150 pet fee | No catsbr• Resort pool access is subject to HOA availability — complimentary, 2–6pm, 6-guest max per session

Wintergreen Mountain Cabin · Hot Tub · Sauna · Mural · Fire Pit · Game Porch

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$559.01