Vacation Home Rentals By Owner In Wintergreen Resort, VA

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

$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

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

Welcome to our cozy 4-bedroom, 3.5-bathroom home in Wintergreen Resort, VA. Enjoy a spacious living room with a fireplace, a dining room seating six, and a kitchen counter for two. Relax in the hot tub, gather around the fire pit and grill, or unwind in the comfortable bedrooms with provided sheets and blankets. The master bedroom is on the first floor, while three bedrooms are upstairs. A workspace and minibar are also available. During springtime, you'll have access to the community pool! brbrbrWe value your privacy and want to ensure that you have a relaxing and uninterrupted stay. As such, our approach is to provide you with complete privacy throughout your time at the house. However, we also understand that sometimes you may need assistance or have questions during your stay.brbrRest assured, our dedicated team is available to assist you whenever you need. Whether you have inquiries about the property, need recommendations for local attractions, or require any other assistance, our team is just a phone call or message away. We are committed to making your stay as enjoyable as possible, and we are more than happy to address any concerns or provide any necessary support.brbrYour comfort and satisfaction are our top priorities. We strive to strike the perfect balance between respecting your privacy and ensuring that you have access to the assistance you need. Enjoy the peace of mind knowing that a helpful team is available to support you whenever necessary.brbrDrive the Blue Ridge Parkway, Get Breathtaking Views at Wintergreen Overlooks. Go Tubing Down the Mountain. Have Brunch (or Dinner) at the Devil’s Knob Grill. Hike at Humpback Rocks, Hike to The Plunge. Play/Swim at Lake Monacan. See Upper Shamokin Falls. Take in a Concert (or Theatrical Production). Visit the Nature Foundation at Wintergreen and take part in one of their excursions or events, and the 'Treehouse', an activities area for children near the lodge. For older children there is a large video game room (including a bull-riding ride), put-put golf, snow tubing (or a zip line in the summer) and trampolines. Rejuvenate your body and spirit at Wintergreen spa and refresh your soul in the beautiful mountains. Golf at the Stoney Creek golf course down in the Valley.brbrIn July and August Wintergreen hosts a music festival with concerts, master classes, and lots of related activities. It's a great time to visit. brbrWinter is the prime season at Wintergreen due to its popular ski resort. During winter, the best part of this condo is that you can hit the slopes without having to drive or take a shuttle. Wintergreen offers plenty of activities and entertainment options for guests of all ages, from skiing and snowboarding to golfing and hiking. There are also many great restaurants, shops, and attractions to explore in the area. Don't miss out on the chance to experience Wintergreen in comfort and style. During winter Chair lift and tubing tickets sell out quickly! We recommend buying tickets before you arrive. You’ll find links at wintergreen resort. You may need to reserve ski rentals ahead of time, also (you can rent them from The Ski Barn which is located at the intersection of Rt. 151 and Rt. 664, at the bottom of the mountain.brbrThings to do around Wintergreen, VA:brbr1. Wintergreen Resort: This ski resort offers skiing, snowboarding, and other winter sports activities in the winter, and hiking, golf, music festival and other activities in the summer.br2. Blue Ridge Parkway: Take a scenic drive along this highway, which offers stunning views of the Blue Ridge Mountains. Blue Ridge Parkway and Afton Mountain also offer a variety of trails. The Blue Ridge Tunnel goes under Afton Mountain. Located off State Route 56 you can hike to Crabtree Falls, one of the tallest sets of waterfalls east of the Mississippi River.br3. Crabtree Falls: Hike to the top of Virginia's tallest waterfall, which offers beautiful views of the surrounding landscape.br4. Rockfish Valley Trail: This hiking and biking trail offers stunning views of the Blue Ridge Mountains and the surrounding valley.br5. Bold Rock Hard Cider: Take a tour of this local cidery, which offers tastings of their award-winning hard cider.br6. Stoney Creek Golf Course: Play a round of golf at this beautiful course, which offers stunning views of the surrounding mountains.br7. Sherando Lake Recreation Area: This beautiful lake and recreation area offers swimming, fishing, hiking, and camping opportunities. Please visit their website for more information about fees and schedule.brbrbrbrGuests will enjoy exclusive access to the entire property, ensuring complete privacy and freedom during their stay. Ample parking space is available in a private area. Guests will receive the door code 24 hours prior to their scheduled check-in.brbrDuring the summer, you will have access to the Chestnut Springs Pool on the mountain and the Rodes Farm Pool down in the valley. Spa Day Guests may use the Aquatics & Fitness Center the same day of a full-length Spa service for more information about access and rates please contact the Aquatics & Fitness at Wintergreen ResorbrbrWelcome to our cozy 4-bedroom, 3.5-bathroom home nestled in the serene Wintergreen Resort, Virginia.brbrAs you step inside, you'll be greeted by a spacious living room adorned with a crackling fireplace, perfect for unwinding after a day of adventures on the slopes or trails. The living room seamlessly flows into the well-appointed kitchen, creating a warm and inviting atmosphere for gatherings with family and friends.brbrAdjacent to the kitchen is a beautiful dining room, comfortably seating six guests, with additional seating for two at the kitchen counter. Whether you're enjoying a home-cooked meal or sipping on your morning coffee, this space is sure to be a favorite spot during your stay.brbrStep outside onto the deck and immerse yourself in relaxation with our private hot tub, perfect for soaking tired muscles while enjoying the crisp mountain air. Gather around the fire pit and create lasting memories with loved ones as you roast marshmallows under the starry night sky.brbrInside, each bedroom awaits with cozy sheets and blankets provided, ensuring a restful night's sleep without the hassle of packing extra linens. The master bedroom, located on the first floor, features its own private bathroom for added convenience.brbrVenture upstairs to discover three additional bedrooms, one with its own en-suite bathroom, while the other two share a spacious bathroom. With comfortable sleeping arrangements and ample space for relaxation, our home offers the perfect retreat for families or groups of friends.brbrFor those needing to stay connected, a convenient workspace is available, along with a minibar for added convenience during your stay.brbrExperience the beauty of Wintergreen Resort from the comfort of our inviting mountain home. Book your stay today and create unforgettable memories in this idyllic setting. We look forward to hosting you!brbrAmenities that we offer:brbr1. Wi-Fi: you will have access to Wi-Fi connection, we understand this is essential for many guests who need to stay connected to work, family, or friends.br2. Bedding and linens: we will provide fresh, clean bedding and linens for a comfortable night's sleep.br3. Toiletries: we take care of basic toiletries like shampoo, conditioner, body wash, hand soap, and toilet paper so you don't have to worry about bringing these items themselves.br4. Towels: we will provide towels and a hair dryer during your stay.br5. Kitchen essentials: for your convenience we will provide basic cooking supplies like pots and pans, utensils, plates, and glasses. Also, basic spices like salt, pepper, onion, garlic, parsley and cooking oil.br6. Coffee: Many guests appreciate a good cup of coffee in the morning, so we will provide coffee, sugar and a coffee maker.br7. TV and entertainment: We will provide streaming services like Roku, as well as board games and books for you to enjoy.br8. Air conditioning and heating: We will make sure the temperature is comfortable, regardless of the weather outside.br9. Laundry facilities: you will have access to a washer and dryer, and we will provide a started set of laundry detergent for your convenience.br10. Safety features: the home is equipped with smoke detectors, first aid kit to ensure guests' safety during their stay.

Cozy House at Wintergreen with hot tub/firepit/fireplace & all amenities included and pool access!

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$315.54

Bring the whole family or your friends to this cozy cabin with lots of room for fun and relaxation. Check out the local breweries and wineries, take the kids apple picking, go for a hike or horseback riding, golf, tennis, skiing, and the lake are close by. Amazing sunrises and Founder's Overlook is just one mile away. Skiing is a 3-minute drive and trails are across the street. Take advantage of our fire pit, BBQ, and hot tub outside with Pac Man arcade and board games for indoor fun.brbrOne-story home with ample room for friends and family for four-season fun and relaxation. Gas fireplace, high-speed internet with smart TVs in all bedrooms and living room. Three bedrooms and two full bathrooms sleep up to 9 people (7 beds). 3-minute drive from skiing and close to lots of outdoor activities. Popular rental recently updated.brbrFire pit, grill, and hot tub in backyard. 4 rockers and large swing on front porch, plus ski and boot holders. brbrSheets, towels, basic kitchen and BBQ supplies provided. Up to 2 dogs allowed with pet fee (no cats).

Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$253.43

4min to Ski. Nestled next to a perennial mountain stream in Wintergreen Resport this cozy 3 bedroom, 2.5 bath house with onsite hot tub is the perfect place to getaway with your family or friends! brbrLocated very close to ski slopes, Appalachian Trail, Blue Ridge Parkway and golf courses. brbrEnjoy the outdoors skiing or hiking during the day - or just relax on the deck listening to the sound of the spring water. In the evening drink cocoa by the fire, snuggle up and read a book, or relax in the hot tub.brbrGreat for couples and families alike.

Whispering Creek Hot Tub Pool TennisGolf King Beds

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$267.27

The house easily sleeps eight. There are two queen size beds (one main and second level), two full beds with a twin bunk on top (in loft and basement), and full futon in basement. The kitchen has a blender, crockpot, Keurig, french press, microwave, toaster oven and basic cooking items. There are towels, wash cloths, blow dryer, linens, pillows, and extra blankets for every bed. There is a deck overlooking the forest with gas grill, hammock, table, chairs, and umbrella for delightful outdoor meals. There is a hot tub on the basement level. Two cars will fit in the parking area and there is also on-the-street parking; but with multiple cars, you may want to carpool from the lodge lot. The ski slope is .2 miles at the end of the street (trail marked with pink ribbon). The slope there, Tyro, is not always operational the entire season; however, you can walk down to the Big Acorn lift.brbrUpdate: The house has a brand new stove!

Quiet cul-de sac

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$312.19

READ FULL DESCRIPTION BEFORE BOOKINGbrbrCome relax at our 3 bedroom 2 bathroom condo and enjoy the views of the Devils Knob Golf Course! This condo sleeps up to 10 people comfortably. The main level features 2 bedrooms-one bedroom has a queen bed and a twin, the other has a full sized bed in addition to a bunk bed with a twin on top and a full bed on the bottom. Both bedrooms have their own TV's. The first bedroom is equipped with TV-plus. The second bedroom is not equipped with cable but a Wii U is available for game play making this room great for the kids! The second level features the master suite and offers a comfy king sized bed, it's own TV and an en-suite bathroom! The bathrooms have been recently updated for a more modern feel. All of our guests are supplied with a starter supply of toilet paper, paper towels, dish detergent, and trash bags. brbrOur open floor plan will make you feel right at home. The kitchen is well stocked making cooking and dining a breeze! There is a wood burning fire place in the living room and wood is regularly stocked mid-October through mid- March. We are located within walking distance of the Nature Foundation and hiking trails. Skiing, tubing and shopping are located within a 10 minute drive of the condo. brbrPlease note: We are not considered Resort Members so you will not have access to The Devils Grill, Devils Knob Golf Course or the Wintergarden Spa. You may be able to book a spa treatment to access the indoor pool etc. but we HIGHLY recommend checking with the resort directly to confirm.brbrGuests will have access to the Chestnut Springs and Rodes Farm outdoor pools from 2PM to 6PM. (Memorial Day Weekend-Labor Day Weekend). A valid I.D. will be required for access. Lake Monocan is also available on Sundays, Tuesday-Friday. Check the WPOA website for hours and pricing.brbrOff the mountain, enjoy the many local breweries, wineries and restaurants - Devils Backbone, Wild Wolf Brewery, Bold Rock, Giuseppe's Restaurant to name a few. There is also a grocery store, ABC Store, and Dollar General in Nellysford. br

Condo at Fairway Woods, perfect home base for ski season! ☃️

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

Select Dates for Price

New listing! brbrDiscover mountain living at its finest in this immaculate Trillium villa, ideally situated right across from the Wintergreen Aquatics & Fitness Center, Wintergarden Spa, and the Wintergreen Nature Foundation. brbrThis home overlooks the 17th tee box of Devils Knob Golf Course, offering peaceful views and the perfect spot for scenic walks when the course is closed.brbrJust a short stroll to the Highlands Ski Slope, the shuttle stop, and Fire & Frost Pizzeria, this home combines unbeatable convenience with all the perks of resort-style living.brbrInside, you'll find 2,412 sq ft of turnkey elegance featuring:brbr4 bedrooms, 4.5 bathrooms, including two spacious master suites each with a private bath.brbrMain level with large living room (wood-burning fireplace, wood included), dining room, kitchen, laundry, and half bathbrbrSecond-level primary suite and adjacent secondary bedroom, each with en suite bathrooms.brbrThird level with two additional bedrooms and full baths for guests or family. The kids room has a daybed with trundle and twin bed (and a pac man video console)brbrAdditional highlights include a one-car attached garage with interior access—a rare find on the mountain.brbrThe deck overlooks the golf course and features a cozy gas firepit with seating—perfect for relaxing and enjoying the cool mountain air from one of Wintergreen’s highest elevations.brbrThe property is perfect for families. We are pet-friendly. Please read our pet policy for more details.

New! 4BR/4.5BA Pet-Friendly Golf Front Townhome

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$645.13

With gorgeous mountain views of the Blue Ridge and Blackrock Village this luxury mountain home is one of the largest in the Wintergreen Retreat Luxury Home collection. Featuring 5 bedrooms, 3 full baths, and 2 half baths. The level drive and one step access into the main level allows for easy access. Once inside you will be impressed with the gracious open floor plan and spacious rooms throughout.brbrThe main level master bedroom suite is great for family members with limited mobility. The home also features a backup generator and advanced water conditioning system for our guests comfort and convenience.brbrThe main level includes the soaring, light filled Great Room with cathedral ceiling & stone fireplace, large eat in kitchen with granite, handsome cabinets, tile floors & beautiful master suite with steam shower. Upstairs includes 2 guest bedrooms with multiple sleeping options, full bath and loft with a desk.brbrThe lower level allows for more activities in an additional family room with fireplace, a master suite with full bath, a separate bedroom with a large sleeping capacity, and a half bath. Beautifully maintained and tastefully furnished so you can just walk in and begin enjoying your new Wintergreen vacation!brbr

Modern Luxury Mountain Home within Wintergreen Retreat Collection

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$318.93

Tucked away on a quiet street with sweeping mountain views, this beautifully renovated four-bedroom home offers the perfect Wintergreen getaway. Just one mile from the resort, you’ll enjoy easy access to an array of year-round amenities — from skiing, a full-service spa, and swimming pools to boutique shopping and multiple dining options.brbrThoughtfully updated from top to bottom, the home features all-new appliances, stylish furnishings, and distinctive decorative touches throughout. It’s fully equipped with everything you need for a comfortable stay, blending charm and convenience in every detail.brbrNestled within the Wintergreen Resort community and surrounded by some of Virginia’s best vineyards, breweries, distilleries, and farm-to-table restaurants, this mountain retreat offers endless opportunities for adventure, relaxation, and exploration.brbr⸻brbrAbout Wintergreen ResortbrbrPerched on 11,000 scenic acres along the eastern slopes of the Blue Ridge Mountains, Wintergreen Resort combines breathtaking natural beauty with four seasons of recreation and luxury. Explore miles of hiking trails, cascading streams, and lush forests, or simply relax and take in the panoramic views.brbrThe resort offers something for everyone — including 45 holes of championship golf, exhilarating winter skiing, snowboarding, and tubing, an award-winning tennis program, and a full-service mountaintop spa. Outdoor enthusiasts can enjoy hiking, fly-fishing, and swimming, while food lovers will delight in the resort’s diverse dining options.brbrFamilies will find an abundance of activities, from children’s programs at The Treehouse to seasonal events and curated vacation packages. Wintergreen is also an exceptional destination for meetings and gatherings, with 40,000 square feet of event space, professional services, and spectacular mountain scenery.brbrCommitted to preserving its natural surroundings, Wintergreen partners with The Wintergreen Nature Foundation to protect wildlife habitats and promote environmental education.brbrLocated in the heart of Central Virginia, adjacent to the Blue Ridge Parkway, Wintergreen is just 90 minutes from Richmond and approximately three hours from Washington, D.C. or North Carolina — making it an easy and unforgettable escape.

Experience Wintergreen – Fully Renovated Mountain Retreat with Year Round Views

Wintergreen Resort, Virginia, United States

Bed

2

Bath

8

Sleeps

$346.07

Stay close to the mountain lodge and all the best activities the mountains and Wintergreen Resort has to offer! The classic wood panels, sun-filled gable windows, and serene wooded surroundings of this 3-bed, 3-bath cabin (sleeps 10) with two master bedrooms create the quintessential mountain getaway. Enjoy high-end bedding, stylish mountain decor, and peaceful golf-course views. This is the perfect rental year-round!

5-star property in Wintergreen Resort under new management!

Wintergreen Resort, Virginia, United States

Bed

3

Bath

10

Sleeps

$975.64

Luxury 4100+ sqft designer resort-style home in Wintergreen with top and unique amenities:brbr• 6 bedrooms, 4.5 baths, 12 beds—including 4 King bedsbr• Game & media rooms: Pool table, shuffleboard, arcade machines, 100-inch TV, & home theaterbr• Dining seating: Indoor (10-seat & 6-seat tables) + 3 bar stoolsbr• Outdoor spaces: 10-seat dining, 8-seat couch, fire pit, grill; 6-seat couchbr• Golf course-front with Mountain & Valley viewsbr• Backyard oasis: Hot tub, barrel sauna, cold plungebrbrThe spacebrWelcome to your spacious luxury designer Blue Sky Retreat in the heart of Wintergreen! No stone has been left unturned in crafting this one-of-a-kind home, with meticulous attention to detail throughout. This spacious property is perfect for unforgettable gatherings, offering breathtaking views, high-end amenities, and endless entertainment. Here’s what to expect:brbrSleep in Comfort:br• 6 beautifully designed bedrooms, including 4 King beds, 2 Queen beds, and bunk beds. You can also use the pullout sofabed, and rollaway twin mattress for additional beds.br• Enjoy designer furnishings and plush bedding for a restful night’s sleep.brbrPlay & Relax:br• Dive into the game & media room with a pool table, shuffleboard, arcade machines, Roll & Score, and a 100-inch TV with home theater audio.br• Cozy up in the living room with a large smart TV and premium sound system.brbrDine in Style:br• Host memorable meals with two indoor dining tables (10-seat & 6-seat) and 3 bar stools at the kitchen counter.br• Step outside to the top deck and enjoy al fresco dining at the 10-seat outdoor table, relax on the 8-seat outdoor couch, or fire up the gas grill.brbrUnwind Outdoors:br• Soak in the hot tub, detox in the barrel sauna, or cool off in the cold plunge on the newly designed patio.br• Lounge on the middle deck with a comfortable 6-seat outdoor couch.brbrExperience the Views:br• Nestled on a golf course-front property, the home boasts stunning mountain and valley views year-round. Watch the sunrise with your morning coffee or enjoy the evening glow with a glass of wine.brbrCook Like a Pro:br• The modern kitchen is fully stocked with premium appliances, cookware, and everything you need to create culinary delights. Enjoy the convenience of a Keurig with starter pods to kickstart your mornings.brbrBring your Electric Vehicle:br• Level 2 EV Charger is available at the propertybrbrPerfect for Every Season:br• Whether you’re here for skiing in the winter, hiking in the summer, or simply relaxing in luxury, this home has something for everyone.brbrFrom designer décor and top-notch amenities to a location offering both serenity and adventure, this is more than a home—it’s an experience. Book now to create memories that will last a lifetime!brbrWe have included additional damage protection insurance in the total pricing for your peace of mind!brbrOther things to notebr * Pet-Friendly & Connectedbr* Blue Sky Retreat welcomes your furry friends – we’re proudly pet-friendlybr* Stay connected with high-speed internet throughout the homebrbrbr EV Charging & Parking at Blue Sky Retreatbr• EV Charger On-Sitebr• Located on the front side of the house for easy accessbrCharging cable and Tesla adapter available in the Utility Roombr• Enjoy a seamless, eco-friendly charging experience during your staybr• Ample Parking Spacebr• Spacious driveway fits up to 6 vehicles comfortablybr• No stress about parking—plenty of room for everyonebrbrIndoor Entertainmentbr• Unwind with a variety of board games and puzzlesbrPerfect for cozy nights in or fun family afternoonsbrbrExterior Camera and Motion SensorsbrbrFront Security Camerasbr• An exterior camera is located above the front entrance, facing the driveway.br• A Ring doorbell camera is also installed at the front door.br• Both are in place for safety and to monitor the main entry area only.brbrNo Interior or Backyard Camerasbr• There are no cameras inside the home or in the backyard.br• Your privacy is fully respected throughout your stay.brbr Motion Sensor Lights (Not Cameras)br• Motion-activated lights are installed on the sides and in the backyard.br• These lights are for visibility and safety after dark.br• They do not record and are not equipped with cameras.brbr Accidental Damage Coveragebr• For added peace of mind, your stay includes up to $3,000 in coverage for accidental damage to the property or its contents.br• This protection is already built into the cost of your reservation—no extra fees, no hassle.br• Just relax and enjoy your time at Blue Sky Retreat knowing you're covered.brbrbr Summer Fun & Outdoor AmenitiesbrbrCommunity Pools (Seasonal)brbr• Cool off at two outdoor community pools:br-Chestnut Springs Pool (on the Mountain)br-Rodes Farm Pool (in the Valley)br• Open Memorial Day to Labor Day, daily from 2–6 PMbr• Access included for 6 guestsbrbr Sherando Lake Recreation Areabr• Great for family picnics and outdoor funbr• Entry fee: $8 per vehiclebr• A beautiful spot for nature lovers to explorebrbrStocked Essentials & Comfortsbr Kitchen & Cleaning Suppliesbr• Dishwasher detergent and trash bags provided for your conveniencebr• Basic Starter kit is providedbrbr Bathroom Amenitiesbr• Each bathroom is stocked with body wash, Shampoo, Conditioner, and hand soapbrbr First Aidbr• A first aid kit is available and tucked away in the pantry

LuxuryIHot tubISaunaICold PlungeIGame RoomIViews

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$992.72

Welcome to Stargazer, one of Wintergreen's premier properties. The views are second-to-none throughout the home, and especially from the deck which boasts a hot tub, sauna, firepit, and ample dining space. Inside, you'll love the impeccable design, open floor plan, theater room, and game room. With 6 bedrooms plus two pullout sofas, the home sleeps 16. Plus, pet friendly! Managed by Chris at New School Hosting.brbrThere's a ton to do in the area! Stargazer is about a mile to the slopes and a few minutes’ drive to 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). 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.brbrThe home layout is as follows:brbrDecks:brbr- The small deck directly off of the living room features two Adirondack chairs and a high-top table for 4 to soak in the viewsbr- This deck also connects to the larger lower deck, which features a hot tub, barrel sauna, gas firepit (propane provided), grill with prep table, and a dining set for 10.br- Additionally, there is a small balcony that connects to both the primary bedroom and a hall bedroom with a few chairs (chairs not pictured).brbrMain level:br(Note: there are zero steps required to enter main level from driveway)brbr- Grand living room with big screen TV, wood-burning fireplace, bumper pool table, and separate lounge seating area. Both couches in the living room pull out into beds if needed.br- Screened in porch with endless viewsbr- Dining table can seat 10, plus room for 4 more at the kitchen barbr- Fully stocked kitchen with granite counters, stainless appliances, and gas range.br- BR 1: Master bedroom with king bed and ensuite bathroombr- Half bathbr- Laundry room with full size washer and dryerbrbrUpper level:brbr- BR 2: Primary bedroom with king bed, fireplace, vaulted beamed ceilings, and access to balcony. Ensuite bathroom features double vanities and tile showerbr- BR 3: Queen bedroom with balcony accessbr- BR4: Queen bedroombr- Hall bath with showerbrbrLower level:brbr- Game room with ping pong table, shuffleboard, darts, TV, and additional refrigeratorbr- BR 5: Queen bedroom with access to lower deckbr- BR 6 / theater room: Upper portion of this room has a full bed, and lower portion of this room is set up as a theater with 6 leather chairs and massive TVbr- Hall bath with double vanities and tiled shower/tub combobrbrOther things to note:brbr- Stargazer is pet friendly! We allow up to 4 pets with a $200 pet fee (total, not per pet or per night).br- Wintergreen offers hiking, skiing, snowboarding, tubing, swimming, dining, spa, ropes course, golfing, and much more.br- The driveway can fit 4-5 vehicles, and there are an additional 2 spots along the road directly in front of the house.br- Wifi is fast with a strong signal throughout the house and decks. All six bedrooms, the living room, the game room, and the theater room feature smart TVs where you can access all the main streaming services.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, high chair, and kid dishes 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.

Wintergreen Luxury, Breathtaking Views

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$451.17

You won’t be able to look away from the spectacular Shenandoah Valley and Blue Ridge mountain views offered by this Wintergreen townhouse located 3,600 feet up at the top of the mountain! Enjoy hanging out on the two decks staring out at the spectacular scenery after long days full of skiing, hiking and exploring all that Wintergreen has to offer. With 5 bedrooms and 4.5 bathrooms there is tons of room to bring all your family and friends. The kitchen is fully equipped to prepare your favorite meals. Watch the sunset as you sit in front of the fire and make s'mores. Pets are welcome:) This is one spot guaranteed to leave you with a ‘Positive Altitude!’brbrThe house has 4 floors so lots of space to relax and play in. The bottom floor has a queen-sized bed and ensuite bathroom. The third floor has the primary bedroom with a king-sized bed, ensuite bathroom and porch. There are two more bedrooms that share a full bath; a queen-sized bed in one room and a twin/trundle bed in the other. The second floor has the kitchen, dining room, living room, laundry and half-bath. The fourth floor bedroom/playroom has a twin/trundle and full bath.brThe house has 5 bedrooms which can sleep 10 people. brThere is a great overview just steps away from the house where sunsets are absolutely amazing!! It's also a great place to play the permanent sets of bocce ball, corn hole and shuffle board that are there. We have bean bags and a bocce ball set at the house!brOur home is in the Shenandoah Ridge neighborhood. Renters have access to Stoney Creek golf course and Rodes Farm Pool, both of which are in the Valley, and Chestnut Springs Pool, a heated pool which is on the mountain. Wintergreen Spa is within walking distance of the house and offers amazing spa treatments. Due to a policy of Wintergreen resort, unaccompanied guests (renters) are not allowed access to the gym, indoor pools or Devils Knob golf course. You will have access to the tennis courts and paddle ball courts; court fees apply. brThe area boasts a TON of great breweries, wineries and restaurants. Hiking is one of our favorite activities and there are a plethora of hikes in and around Wintergreen. Check out the tubing during the summer and winter months! brPlease check out www.nelson151.com and www.nelsoncounty.com for up-to-date information on this amazing part of Virginia!! br

Enjoy all 4 seasons at this spacious, pet friendly home! Great views, sleeps 10

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$898.03

Welcome to Highlands Overlook, a designer-decorated home in the heart of Wintergreen. The deck is second-to-none, complete with hot tub, cedar barrel sauna, fire table, dining for 10, grill, smoker, pizza oven, and views everywhere. The light-drenched interior is equally impressive. With 6 bedrooms plus a private game room with pullout sofa, the home sleeps 16 comfortably. Plus, pet friendly! Managed by Chris at New School Hosting.brbrThere's a ton to do in the area! Highlands Overlook is about a mile to the slopes and a few minutes’ drive to 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). 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.brbrThe home layout is as follows:brbrMain level:br(Note: just 1 small step required to enter main level from flat driveway)brbr- Grand living room with big screen TVbr- Dining area for 10, plus room for 4 more at the kitchen barbr- Fully stocked kitchen with granite counters, stainless appliances, and gas range. Dining nook in kitchen features built-in booth seating.br- BR 1: Primary bedroom with king bed. Ensuite bathroom features double vanity and bath/shower combo.br- Game room with pullout sofa, oversized TV, electric fireplace, foosball, shuffleboard, 2 pinball machines, infinity board game table, and additional refrigeratorbr- Half bathbr- Laundry room with full size washer and dryerbr- Upper deck features dining table for 10, oversized propane grill, pellet smoker, and pizza ovenbrbrLower level:brbr- BR 2: King bed with lower deck accessbr- BR 3: King bed with lower deck accessbr- Hall bath with shower/tub combobr- Workspace area at end of hallwaybr- Lower deck features hot tub, barrel sauna, seating area with propane firepit, and multiple places to sit and enjoy the viewbrbrUpper level:br- BR 4: King bed with viewsbr- BR 5: King bedbr- BR 6: Bunk room with 2 sets of twin-over-twin bedsbr- Hall bath with shower/tub combobr- Loft area with couch, rocking chair, and incredible viewsbrbr- Highlands Overlook is pet friendly! We allow up to 4 pets with a $100 pet fee (total, not per pet or per night). We provide some helpful supplies for pet-owners.br- Wintergreen offers hiking, skiing, snowboarding, tubing, swimming, dining, spa, ropes course, golfing, and much more.br- The end of our flat gravel driveway can fit 3 vehicles side-by-side, plus another 3-4 vehicles parked single file down the driveway. So if you have 4 or more vehicles, be prepared to have to move cars around some if somebody is blocked in.br- Wifi is fast with a strong signal throughout the house and decks. Four of the six bedrooms, the living room and game room, feature smart TVs where you can access all the main streaming services.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, high chair, baby monitor, and kid dishes providedbr- 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.

Designer Home w/ Incredible Views, Sleeps 16

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$667.69

One of the best Airbnb's I have rented! House was beautiful and pictures don't do justice! CandicebrbrWelcome to Sundown Sanctuary! A stunning 6-BR home for up to 14! Imagine soaking in the hot tub under the stars, telling stories around the glowing fire, & savoring meals in the inviting outdoor dining area. Kids will love the playground & yard games while you relax & recharge. Inside you'll find modern finishes & thoughtful touches that create the perfect space for lasting memories. Plus, pet friendly!brbrThe house is in the resort and is a 5 minute drive to the slopes, dining, and the many other Wintergreen attractions. Venture just 15 minutes from the house and you’ll discover some of the state’s best hiking trails along the Blue Ridge Parkway, plus more than a dozen wineries, breweries, and distilleries within a 30-minute drive. During the summer, enjoy Sherando Lake and Lake Monocan with sandy beach entrances, or take a dip in the heated community pool.brbrWhen you open the door to this beautiful home you’ll see every inch has been thoughtfully and professionally decorated. The open floor plan welcomes you with a spacious entry for luggage and coats, then opens into a stunning living area with a stone fireplace, smart TV, and soaring ceilings! brbrbrThis place is amazing inside and out !!! Absolutely gorgeous, so tastefully decorated and felt so cozy !!! Everything we needed.br- The Stoll FamilybrbrbrThe home layout is as follows:brbrMain level:brbr• Living room with wood burning fireplace (firewood provided)br• Dining area with space for 8-10 at the main table, plus another 4 at the adjoining barbr• Covered porch with large 12 person outdoor dining table and cozy swinging daybedbr• Newly renovated and fully stocked kitchen with a suite of stainless appliances and everything you need to prepare large meals (including spices)br• Fully loaded Keurig coffee/tea bar and hot cocoa stationbr• BR 1: Master bedroom with king bed, additional seating area, desk/work space, and back porch accessbr• Full bath 1: Ensuite bathroom to BR 1 with shower/tub combobr• BR 2: Additional master bedroom with king bed and reading chairbr• Full bath 2: Ensuite bathroom to BR2 with shower/tub combobr• Half bathbr• Laundry area with full size washer and 2 dryers to dry the whole group's ski clothes in record time ;)brbrUpstairs:brbr• BR 3: Bunk room with two sets of twin-over-twin bunk beds, plus a climbing wall, Lego wall, and infinity game table with tons of built-in digital board gamesbr• BR 4: King bedroombr• Full bath 3: Jack-and-Jill bathroom between BR3 and BR4, with shower/tub combobr• BR 5: King bedroombr• BR 6: King bedroombr• Full bath 4: Jack-and-Jill bathroom between BR5 and BR6, with shower/tub combobrbrBackyard:brbr• Spacious 7 person hot tub with custom-built bar surrounding it, so you can choose to be social even if you don't want to get in :)br• Outdoor living area under the gazebo with big screen outdoor TVbr• 6 burner stainless steel propane grillbr• Wood burning fire pit surrounded by 10 Adirondack chairs. (Firewood is provided)br• Play set with swings, slide, and climbing wallbr• Several yard games including corn hole, spike-ball, kan jam, ladder ball, etcbrbrThe king beds for everyone were such a great touch! And the kids absolutely loved the bunk room with the climbing wall, game table and lego closet! The outdoor space was perfect for relaxing and the house had everything we could possibly need; fully stocked and then some! The home was very kid-friendly, which made our stay even more enjoyable! I can't forget the sound machines in every room and the nice bed linens!! My daughter loved the bedding so much she purchased it for her own bed before we even got home ! -SharonbrbrGuest accessbrGuests have access to the entire home.brbrOther things to notebr• Sundown Sanctuary is pet friendly! There is a $100 total pet fee for your visit, which will cover up to 4 pets (please ensure to indicate how many pets you are bringing in the guests section).br• A dog bed, blankets, and food and water bowls are providedbr• Baby gear provided: playpen, stroller, high chair, monitor, potty seat, and plenty of plate sets and cupsbr• Wintergreen offers hiking, skiing, snowboarding, tubing, swimming, dining, spa, ropes course, golfing, and much more.br• While there are 3 steps required to access the property, once inside, the main level has two master bedrooms, plus the kitchen, living / dining area, and back porch.br• Ample parking for 6+ vehicles is available in the flat, paved driveway.br• Wifi is fast with a strong signal throughout the house and deck. Each bedroom (aside from bunk room), great room, and even backyard features a smart TV where you can access all the main streaming services!br• We provide a fully stocked coffee/tea/hot cocoa bar with multiple coffee drip and Keurig options.br• Linens and towels provided.br• 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, high chair, baby monitor, stroller, baby gate, and kid dishes / utensils provided.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.br• 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 cannot be held responsible for late or undelivered packages. Additionally, we charge $25 for any return services requested, in addition to actual postage.brbrTips for a Happy Hot Tubbr- Be sure to unclip the hot tub cover before removing it.br- Please do not put anything besides people in the hot tub (like mulch or toys).br- If the water level doesn’t cover the jets, you can use the hose to add water. Please disconnect the hose when done, especially in cold weather when it could freeze.br- Always put the cover on the hot tub when not in use - this keeps the hot tub warm & filled with water. Using the plastic clips helps keep it from blowing off.br- For safety reasons, please don’t add chemicals to the hot tub yourself. If the water looks murky or has a smell, let us know, and we'll have our hot tub expert come by to treat it.br- Do not drain the hot tub.br- There's no need to turn off the hot tub. It may run the jets on low periodically to circulate water through the filter—that’s totally normal.br- Use plastic drinkware around the hot tub.

Luxury Oasis - Family & Pets - Outdoor Lounge

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$388.84

Fantastic Mountain Views & Close to the Resort hub.brBright and open Wintergreen 4 bedroom 3 full bath home perfectly situated close to the top of the mountain. Gorgeous breathtaking mountain and valley views from the house, multi-level deck, with hot tub. Sleeps 10 with large harvest dining table, two-story family room and a separate rec room in the basement. A large upper deck with casual seating around the propane fire pit table. Plus a separate picnic table and propane gas grill. A single car garage w/ping pong table.

Wintergreen Resort - Mountain home w/4-bedroom 3 bath, Hot Tub & Wifi

Wintergreen Resort, Virginia, United States

Bed

Bath

Sleeps

$256.32

Welcome to our mountain home at Wintergreen Resort! We fell in love with this house for the same reasons that we know you’ll love it. There’s plenty of sleeping space with 4 bedrooms, each with its own sliding glass door that opens onto a deck. There are three decks on the house, so plenty to choose from!brbrThe upstairs master has its own bathroom and opens onto the upper level front deck. The master has a brand new 12” king memory foam mattress and a brand new bed rustic bedframe. The room has beautiful vaulted ceilings and plenty of closet space. The other three bedrooms are downstairs and each open onto the lower level deck, which has a porch swing. The downstairs is perfect for either the children or visiting families. One bedroom has a double bed, one has a twin over double bed bunk bed, and one has two twin beds. The bedrooms on the lower level share one bathroom that breaks down into three separate rooms: one with a sink and toilet, one with a shower, and one with a sink to allow maximum use of the space regardless of how many folks are staying on the lower level. brbrThe main living area is on the upper level and enjoys nice mountain views from the front with two sliding glass doors that open onto the front upper deck. There is a half bath right off of the living area, along with a door that leads out to the back deck (w/ grill). The living room, dining room, and kitchen are all connected as one, open living area under beautiful vaulted natural hardwood ceilings. There is a large leather sectional sofa, a brand new and large flat screen TV, and a brand new dining set in the living room, along with several other updates in décor. All of these all come together to give this house that wonderful mountain house feel.brbrAs far as amenities, we have a washer/dryer, a basic cable package, and high speed internet (wired and wireless). Right outside the door, you have complete access to all the great outdoors has to offer. The Wintergreen Resort spa and golf course are right around the corner, and the lodge and skiing is only 5 minutes away. There are many wineries and breweries in the area that are perfect daytime activities year round. Don’t forget the Blue Ridge Parkway is only a few minutes away, as well!brbrAt this point, we’d like to stay away from allowing pets, but feel free to email for specific pet requests and we might be able to accommodate.

Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck

Wintergreen Resort, Virginia, United States