Best Vacation Rentals in Wintergreen Resort

Top Vacation Rentals in Wintergreen Resort

Plan your perfect getaway with our selection of vacation rentals in Wintergreen Resort. Each choice offers a blend of comfort and local charm, ideal for families and groups.

Vacation Rentals in Wintergreen Resort
Serene Hideaway with Views, 1 Mi to Hike and Ski!
House
Wintergreen, VA, USA

Both parking on-site and free Wifi are accessible at Serene Hideaway with Views, 1 Mi to Hike and Ski!. The air-conditioned vacation home is composed of 3 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Shenandoah Valley Regional Airport is 43 miles from the property.

Guest Reviews:

- "Perfect!" - "Wonderful weekend with old friends."

Vacation Rentals in Wintergreen Resort
Wintergreen Resort Home w/2 Decks + Ski Access!
Cottage
115 Tyro Ln, Nellysford, VA, 22967, USA

Close to skiing, this smoke-free cottage brings it all within reach. There's convenient onsite parking, so you can leave your vehicle behind and head out to Wintergreen Resort and George Washington National Forest, just a short walk away.

Relax by the outdoor pool or sip a drink in the garden of this cottage, which also features a porch or lanai and a firepit. As for the great indoors, you can come inside and enjoy the free WiFi and TV.

This 3-bedroom, 2-bathroom rental features a living room, a fireplace, and a desk. The kitchen is equipped with an oven, a stovetop, and a dishwasher, as well as a coffee maker, an ice maker, and a microwave.

Amenities:

Laundry • Sports/Activities • Security/Safety • Entertainment • Balcony/Terrace • Fireplace/Heating • Tv • Pool • Child Friendly • Parking • Kitchen • Other

Vacation Rentals in Wintergreen Resort
Wintergreen Resort Home with 2 Decks and Ski Access!
House
Roseland, VA, USA

This vacation home offers a garden as well as a bar. There's an outdoor pool and guests have access to free Wifi and parking on-site. The vacation home consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are featured in the vacation home. The accommodation has a fireplace. Skiing is possible within the area and Wintergreen Resort Home with 2 Decks and Ski Access! offers ski-to-door access. Shenandoah Valley Regional Airport is 42 miles away.

Amenities:

Internet • Parking • Accessibility • Fireplace/Heating • Guest Services • Skiing • Security/Safety • Bar • Other • Sports/Activities • View • Pool

Vacation Rentals in Wintergreen Resort
Wintergreen Home w/Hot Tub, Deck & Mountain Views
Cottage
26 Shagbark Lane, Nellysford, VA, 22967, USA

Close to skiing, this family-friendly cottage brings it all within reach. There's convenient onsite parking, so you can leave your vehicle behind and head out to Wintergreen Resort and George Washington National Forest, just a short walk away.

This 3-bedroom, 2-bathroom rental features a computer station, a BBQ grill, a fireplace, and air conditioning. Connect to the free WiFi, or get cozy in front of the flat-screen TV; there's also a video-game console and a DVD player. The kitchen is equipped with an oven, a stovetop, and a dishwasher, as well as an ice maker, a microwave, and cookware. And you won't have to pack extra clothes, because you'll also have a washing machine. Other amenities include bed sheets, an ironing board, a ceiling fan, and heating.

Amenities:

Laundry • Child Friendly • Internet • Tv • Air Conditioner • Fireplace/Heating • Kitchen • Other • Business Services • Sports/Activities • Entertainment • Security/Safety

Vacation Rentals in Wintergreen Resort
Wintergreen Home with Hot Tub, Deck and Mountain Views
House
Wintergreen, VA, USA

This vacation home provides air-conditioned accommodations with free Wifi. Guests have access to a hot tub and spa center. Wintergreen Home with Hot Tub, Deck and Mountain Views features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. A flat-screen TV with cable channels, game console, and DVD player, as well as a computer and a laptop are provided. The property has an outdoor dining area. Ski-to-door access is available on-site and skiing can be enjoyed close to the vacation home. Shenandoah Valley Regional Airport is 42 miles away.

Amenities:

Other • Guest Services • Sports/Activities • Accessibility • Wellness Facilities • Transportation/Shuttle • Parking • Security/Safety • Internet • Skiing • Hot Tub • Fireplace/Heating

Vacation Rentals in Wintergreen Resort
Wintergreen Resort Home: Close to Slopes & Trails
Cottage
76 Pedlars Point, Nellysford, VA, 22958, USA

Located in Nellysford, this welcoming cottage lets you experience it all. Wintergreen Resort and George Washington National Forest are just a short walk away, so leave your car at the property, which offers onsite parking.

This 4-bedroom, 3-bathroom rental features a living room, a BBQ grill, a fireplace, and air conditioning. Try your hand at billiards, or enjoy the free WiFi and TV. Be sure to check out the kitchen, stocked cookware and paper towels. Other amenities include bed sheets, a ceiling fan, and heating.

Amenities:

Air Conditioner • Tv • Kitchen • Parking • Other • Fireplace/Heating • Security/Safety • Child Friendly • Barbecue/Outdoor Cooking • Internet

Vacation Rentals in Wintergreen Resort
Walk to Ski Slopes Wintergreen Resort Treehouse
House
Beech Grove, VA, USA

Both parking on-site and free Wifi are accessible at Walk to Ski Slopes Wintergreen Resort Treehouse. The air-conditioned vacation home consists of 3 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a bath and a hair dryer. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Shenandoah Valley Regional Airport is 42 miles from the property.

Amenities:

Fireplace/Heating • Other • Sports/Activities • Accessibility • Parking • Security/Safety • Child Friendly • Guest Services • Internet

Vacation Rentals in Wintergreen Resort
Designer Home w\/ Fire Pit ~ 70 Steps to Slopes!
Cottage
749 Pedlars Edge Dr, Nellysford, VA, 22967, USA

Just a short distance from ski lifts, this smoke-free cottage lets you experience it all. There's convenient onsite parking, so you can leave your vehicle behind and head out to Wintergreen Resort and George Washington National Forest, just a short walk away.

As you settle into this 5-bedroom, 4.5-bathroom rental, you'll find a fireplace and air conditioning. Enjoy the free WiFi and TV. Prepare a home-cooked meal in the kitchen, complete with an oven, a stovetop, and a dishwasher, as well as an ice maker, a microwave, and cookware. Other amenities include bed sheets, an ironing board, housekeeping, and heating.

Amenities:

Accessibility • Kitchen • Security/Safety • Wheelchair Accessible • Tv • Child Friendly • Air Conditioner • Pool • Bedding/Linens • Other • Fireplace/Heating • Guest Services

Vacation Rentals in Wintergreen Resort
Bear Necessities with Wintergreen Advantage
House
Wintergreen, VA, USA

This vacation home provides air-conditioned accommodations with a balcony and free Wifi. There's parking on-site, and the property offers an electric vehicle charging station. Bear Necessities with Wintergreen Advantage features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are provided in the vacation home. The accommodation is non-smoking. Guests at the vacation home can enjoy skiing nearby, or make the most of the outdoor pool. Shenandoah Valley Regional Airport is 43 miles away.

Amenities:

Ev Charge Station • Skiing • Pool • Child Friendly • Security/Safety • Parking • Pet Friendly • Wellness Facilities • Internet

Vacation Rentals in Wintergreen Resort
Charming 4-bedroom home with WiFi, game room and more near Wintergreen Resort!
House
Nellysford, Virginia, USA

Bear Tracks - the perfect Wintergreen Resort vacation home! This charming home offers a tranquil retreat with various living spaces - 1 king bed, 2 queen beds, and a twin bed with trundle, there's plenty of space for everyone to relax and unwind. The house is equipped with AC, heating, WiFi, Smart TVs, washer/dryer, and a game room. The kitchen is fully equipped including Keurig machine and coffee pods. The main level living area has large sectional and large screen Smart TV. The lower level includes a full size pool table, large screen TV, queen bedroom and large living area. All bathrooms feature amenities such as a soap, shampoo, conditioner, hair dryer, bathtub, and shower. Conveniently located 1.2 miles from Wintergreen Resort and 1.4 mile from The Plunge Snow Tubing Park. Whether you're exploring the nearby attractions or simply enjoying the peaceful surroundings, our property is the perfect place to create lasting memories. We look forward to hosting you at our mountain home!

Guest Reviews:

- "The home was beautiful and roomy inside. Had everything we needed. When I had a question about something and reached out to the owner Pam, she responded quickly. We enjoyed it so much, we will definitely come back again. " - "Our family had a wonderful visit here at Wintergreen. This house was perfect for us. It was great having the pool table to enjoy and there was a wonderful selection of puzzles and games and even some toys for our toddler grand daughter to play with. The kitchen was well stocked with everything we needed(I would have to say it was one of the best stocked kitchens we have seen in a VRBO). Pam was great to work with and was very responsive. I would definitely recommend! The only thing that I might would change would be to have shades that wouldn't take away from the beautiful views of the windows in the master bedroom and bathroom but that could be pulled down at night to give more privacy."

Vacation Rentals in Wintergreen Resort
Antlers Aweigh with Wintergreen Advantage
House
Wintergreen, VA, USA

Both free Wifi and parking on-site are accessible at Antlers Aweigh with Wintergreen Advantage free of charge. Offering direct access to a patio, the air-conditioned vacation home consists of 4 bedrooms. Featuring a balcony with mountain views, this vacation home also comes with a cable TV, a well-equipped kitchen with a dishwasher, an oven, and a microwave, as well as 3 bathrooms with a bath and a hair dryer. The property has an outdoor dining area. Guests at the vacation home can enjoy skiing nearby, or make the most of the outdoor pool. Shenandoah Valley Regional Airport is 43 miles from the property.

Amenities:

Child Friendly • Internet • Parking • Skiing • Security/Safety • Pool • Wellness Facilities

Vacation Rentals in Wintergreen Resort
Pedlars Big Mountain Home at Wintergreen
House
564 Pedlars Point, Nellysford, VA, 22967, USA

Located in Nellysford, this 7-bedroom, 5-bathroom vacation home lets you experience it all. Fans of nature and the outdoors will love being within a 5-minute walk of George Washington National Forest and 21 minutes by car from Sherando Lake Recreation Area. Thanks to the convenient nearby parking, you can either leave your vehicle behind and enjoy a short 5-minute walk to Wintergreen Resort, or easily tackle the 17-minute drive to Bold Rock Hard Cider Nellysford Cidery.

While you're here, you can enjoy all the comforts of home and more, including free WiFi and a garden.

Amenities:

Child Friendly • Internet

Vacation Rentals in Wintergreen Resort
Shangri-la ! A Perfect Getaway for everyone !
Ski Chalet
27 Pedlars End, Beech Grove, VA, VA 22967, USA

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

Amenities:

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

Vacation Rentals in Wintergreen Resort
Large and Luxurious Exec 5BR Chalet
House
Wintergreen Resort, Virginia, USA

House, 5 Bedrooms, 4.5 Baths, (Sleeps/Max occupancy 10 people)
Important notes for prospective renters:
1) Our house gets rave reviews - see guestbook comments
2) House is very close (100 steps) to the Lower Tyro ski slope and under a 1 mile drive to Mountain Inn

Enjoy all four seasons of the Blue Ridge Mountains in our large, well furnished, executive-level retreat. Located at the top of the mountain in Wintergreen Resort, which is located in beautiful (one stoplight) Nelson County, and just southwest of Charlottesville, VA (Monticello and the University of Virginia). Wintergreen is the perfect mountain retreat for outdoor enthusiasts who enjoy hiking, biking, golf, tennis, skiing, and other activities, as well as those who just want to kick back and relax. Locally, there are many interesting activities, such as many breweries and vineyards, shopping, fishing, kayaking, apple picking, and sightseeing at significant historical sites.
Our spacious, 3000-plus-square-foot, luxury, vacation home is conveniently located just approximately 100 steps away from the Tyro ski slope and across the street from a hiking trail. Our home has the true mountain feeling with a wonderful wooded site and some views of the ski slopes and the mountains.
This non-smoking home features:
* Upper level: two large master bedrooms with king-size beds; great room and gourmet kitchen (with breakfast bar) with soaring tongue-and-groove wood ceiling and lots of windows; wood burning fireplace and LED TV with surround sound, private executive office with broadband internet, powder room, deck and gas grill.
* Lower level: master bedroom with queen-size bed and full bathroom, and two additional bedrooms (one with queen bed and one with double + bunk bed) that share a full bathroom; highly functional mud room to unwind after a day on the slopes that includes a ski and snowboard stand, benches to remove your shoes or boots, plenty of hooks for your jackets and gloves, and washer and dryer; living/recreation room with a 55' HD TV and surround sound, Xbox 360 and games, and table and chairs for card games, puzzles, or using your laptop with a wireless broadband internet connection.
Overall, our well-appointed vacation house is ideal for large families or shared by several families, or as your corporate retreat. This is a fabulous home for a very reasonable price.
Keywords: Mountain House, Mountaintop, Ski Slopes, Luxury, Wintergreen, Walk to Ski, Snowboard, skiing, wood fireplace

-- POLICIES --

- No smoking anywhere on premises, inside or out

- No pets allowed

- No events, parties, or large gatherings

-No more than a total of 10 people to occupy the house (all adults and children count toward the total). If additional people are found at the property an additional $100 per night/per person will be charged.

- Must be at least 30 years old to book

- The person who rents and pays (primary renter) must occupy the house during the complete stay

- If there is damage that makes it so the succeeding renter cannot occupy the space, the renter responsible for the damage agrees to pay for the succeeding renters stay

- NOTE: Your safety matters. This property features 2 exterior surveillance cameras, around the perimeter of the home, facing out

Guest Reviews:

- "Thoroughly enjoyed Wintergreen and this property suited our family perfectly. We had 3 families - grandparents (2) daughter plus husband and one daughter (age 4) plus daughter and husband and 4 kids ages 2-9. Very clean - responsive owner and great location on the mountain. Loved it" - "We had a great time at this house! Well-equipped, perfect number of sleeping spaces, roomy." - "This property was idea for us. There were four couples and we each had our own bedroom and bath. Great living room and large eat-in kitchen. Every item that we needed was provided. Unit was spotless and met all our needs."

Vacation Rentals in Wintergreen Resort
Wintergreen Home w/Hot Tub, Deck & Mountain Views
House
Wintergreen, Virginia, USA

The ultimate Blue Ridge Mountain getaway awaits at this 3-bedroom, 2-bath vacation rental! This home boasts ski-in/out access to Wintergreen Resort's main ski slope, along with a private hot tub surrounded by towering trees that create the perfect après ski setting! Whether you're traversing the nearby Appalachian Trail, exploring local breweries and vineyards, or simply want to escape the stresses of daily life, this Virginia retreat will provide the perfect home base for all your excursions.

-- THE PROPERTY --

Ski-In/Ski-Out | Free WiFi | 1,300 Sq Ft | Wii & Playstation Gaming Consoles

Hit the slopes of Wintergreen when you book a stay at this quaint home, perfect for families or small friend groups looking to plan a trip to escape city life.

Bedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: 2 Twin Beds | Additional Sleeping: Pack n' Play

OUTDOOR LIVING: Private hot tub, wraparound deck, patio furniture & outdoor dining area, gas grill
INDOOR LIVING: 3 cable TVs, DVD player, video library, board games, vaulted ceilings, gas fireplace, ceiling fans, spiral staircase, 6-person dining table, desk area
KITCHEN: Fully equipped w/ stainless steel appliances, coffee maker, toaster, toaster oven, water filter, ice maker, spices, Crock-Pot, dishware/flatware
GENERAL: Central heating & air conditioning, washer & dryer, linens, towels, complimentary toiletries, hair dryer
FAQ: Step-free access, bedroom & bathroom on 1st floor, quiet hours (after 10:00 PM)
PARKING: In front of house (2-3 vehicles), street parking

-- THE LOCATION --

OPT OUTSIDE: Wintergreen Resort (0.6 miles), Devils Knob Overlook (2.2 miles), Three Ridges Hike - Appalachian Trail (4.0 miles), Three Ridges Overlook (4.5 miles), Blue Ridge Parkway (17.6 miles)
VINEYARDS: Afton Mountain Vineyards (21.6 miles), Delfosse Vineyards & Winery (22.6 miles), Brent Manor Vineyards (23.6 miles), Mountain Cove Vineyards (27.8 miles)
BREWERIES: Devils Backbone Basecamp Brewpub (7.7 miles), Wild Wolf Brewing Company (10.2 miles), Brewing Tree Beer Co (16.9 miles), Wood Ridge Farm Brewery (19.7 miles), Blue Mountain Brewery (20.6 miles)
AIRPORT: Charlottesville-Albemarle Airport (47.3 miles)

-- REST EASY WITH US --

Evolve 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.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: Please observe quiet hours after 10:00 PM
- NOTE: Evidence of smoking at the property will result in a $500 fine
- NOTE: Evidence of parties at the property will result in a $500 fine
- NOTE: If furniture or electronics is moved or altered, additional fees may apply

Guest Reviews:

- "We had a great 4 night stay! The location and access to slopes can’t be beat. And communication with the host, Deb, was fabulous. We appreciated that the house was well stocked things like hand soap, detergent, etc. Would definitely stay again!" - "We had an absolutely wonderful time at this very conveniently located cabin on the top of the mountain. Our kids loved the easy access to the slopes and the views were fantastic. Thanks for all of the hospitality Deb!-Amos"

Vacation Rentals in Wintergreen Resort
Beautiful Mountain Views, Steps to the slopes!
House
wintergreen, Virginia, USA

Eagle's Lookout is located in Wintergreen's Treeloft Village, just 100 steps from the ski slopes. Our house delivers stunning year-round Southwest views from almost every room. Adjacent to protected greenspace and actually perched above a scenic overlook, you'll enjoy winter sunsets in a quiet, peaceful setting and be the first to take advantage of new snow by rolling out of bed and hitting the slopes!

All the comforts of home during your mountain getaway... Inside, vaulted ceilings and a wall of windows open the space. The updated kitchen and baths all boast granite counters and new fixtures. The dining area seats 6-7 people comfortably, and the living room features leather seating and a wood burning fireplace for cozy evenings. The master bedroom has a king bed and private bath, and the 2nd downstairs guest room has a queen bed and a rollaway cot available. A spiral staircase leads to the upstairs loft bedroom with two sets of bunks and its own tv area. Great for the kids! All rooms have flatscreen cable TVs and WiFi internet is included.

Guests really appreciate our enlarged back deck, with a new gas grill and gorgeous year-round view! And a heated mudroom addition provides a washer/dryer & plenty of room to suit up for the slopes and store all your gear out of the way. This is a feature very rare in Wintergreen slope side houses!

Enjoy Wintergreen Resort any time… so much more than just a winter getaway! It is a multi-seasonal family destination comprised of 125 acres of skiing, public golf at Stoney Creek (27 hole course in the valley-open year round!), Wintergarden Spa, summer music festival, 30+ miles of hiking trails that connect to the Appalachian Trail, summer outdoor swimming pools and tennis court, fishing, kayaking, and relaxing at Lake Monacan beach. Come and enjoy!

In summer come to escape the heat at Wintergreen! Typical mountaintop highs only in the 70s make this a perfect place for outdoor fun. Check out the new slide at Lake Monocan or pamper yourself at the resort spa. Tubing, trampolines, climbing or archery await at Discovery Ridge. We are within walking distance of the Mountain Inn, gift shop and restaurants, Blackrock Market, the Discovery Ridge Adventure Center and multiple hiking trailheads. Plenty of adventure to choose from! You can even watch the 4th of July fireworks from the slopes across the street!

In October, our deck is the spot for soaking in the Fall colors! And cooler temps make autumn the perfect time for golf at Stoney Creek and to enjoy the many outdoor activities in the valley. Explore the Nelson County area with dozens or vineyards, breweries, great dining, historic sites and scenic hikes.

Planning ahead? We have the perfect winter location! Our home is across the street from the Eagle's Swoop run at the top of the Big Acorn Lift. This ski area is rated intermediate. Eagle's Swoop is one of the first runs to open each season and operates for both day & night sessions. It is only about a 2-minute walk to the slope… Easy to stop home for cocoa or ski to the Mountain Inn for dinner, yet far enough so you won't be bothered by the snowblowers and night skiers in the evenings.

(Note: No central AC in these original Treeloft houses, but cool summer nights, the 3500 ft elevation and mountain breezes usually do the job well, as our many repeat summer guests will attest. And we do provide single AC units in each of the downstairs rooms and many extra fans just in case of the rare extreme heat!)

Keywords: House, Wintergreen, View, Ski, Mountain

Guest Reviews:

- "We LOVED our stay and plan to revisit. Easy walk for our 7 and 11 year old to the slope. Quiet with beautiful views!!!!! Such a special place!!" - "We loved this house in Wintergreen! The cabin was perfect with all the amenities. It was clean and comfortable. The views were spectacular as it is right across from a look out! Perfect location in Wintergreen. Walking distance to the local market and The Edge restaurant. Very close to wineries and breweries. Hiking trails are right there across the road and along the road. Ski slopes are steps away. The owners also had a book full of brochures and information that was really useful for visiting the area. The owner was very communicative and offered suggestions on where to go, what to see. Thanks for a great vacation!!"

Vacation Rentals in Wintergreen Resort
Modern Mountain Retreat: Hot Tub, Chef's Kitchen, Game Room & Ski Access
House
Nellysford, Virginia, USA

Welcome to your dream getaway at Wintergreen Resort — a stylish, fully renovated mountain retreat that blends high-end comfort with family-friendly fun. Perched at elevation with panoramic Blue Ridge views, this five-bedroom home features expansive living spaces, a massive fenced yard, and upgraded amenities tailored for both relaxation and recreation.

🛋 TWO Stunning Living Areas for Ultimate Entertaining
Inside, discover two levels of beautifully designed gathering spaces.
Downstairs: a spacious game lounge with pool table (ping-pong topper included), foosball, oversized sectional (with queen sleeper), smart TV, and a game/puzzle table — all opening to a large porch and 7-person hot tub, perfect for stargazing or soaking after a ski run.
Upstairs: a sun-drenched great room with soaring ceilings, breathtaking mountain views, a cozy stone fireplace, and plush seating around an HDTV — ideal for movie nights or game day.

🍽 Chef’s Kitchen + Designer Dining
The gourmet kitchen features eco-friendly recycled paper countertops, an induction cooktop, two dishwashers, wall oven, convection oven/microwave, beverage fridge, and two sinks — plus direct access to a gas grill for easy outdoor dining.
Enjoy meals around the elegant 10–12 person dining table or gather at the spacious kitchen island.

🛏 5 Bedrooms + 5 Bathrooms | Sleeps 14

Primary Suite (upstairs): King bed, gas fireplace, smart TV, two sitting areas, sunrise & sunset views, spa-style jetted tub, TV in the bathroom (!), and walk-in tiled shower.

Downstairs:

Queen guest suite w/ HDTV + luxury walk-in shower

Double bed guest room w/ en suite tub/shower

Two themed bunk rooms (each with private bathrooms)

Plus: Queen sleeper sofa in the game room

Outdoor Perks

Oversized fenced yard — a rare find in the mountains — perfect for kids and pups to run free

Two-story deck with plenty of seating

7-person hot tub under the stars

Gas grill for mountain cookouts

TWO member-only parking passes for ski-out lot access

Year-Round Adventure
Whether it’s ski season, leaf-peeping, or summer hikes, this home offers the perfect launchpad. Minutes to slopes, hiking trails, and golf — and loaded with amenities to keep everyone entertained when you’re home.

Guest Reviews:

- "Great place wirh best view The whole family loved it Thanks" - "The house was great for our family of 8…5 adults 2 children (with beds to spare for more kids!). The view from the upper deck was spectacular…the highlight of the week for sure. Would love to spend the rest of my mornings and evenings just relaxing there!" - "CLEAN MODERN HOME WITH A BEAUTIFUL VIEW AND PLENTY OF ROOM FOR A LARGE GROUP. HIGHLY RECOMMEND THIS LOCATION."

Vacation Rentals in Wintergreen Resort
Remodeled 3BR/2BA Ski Chalet off Tyro Slope
House
Roseland, Virginia, USA

This quaint remodeled Austrian styled 3BR/2BA ski chalet just one row off the Tyro Slopes. The unit has been completely renovated inside and out including new siding, new insulation, new kitchen, new bathrooms with heated floors, all new flooring and paint throughout, new deck, and expanded parking. This house is extremely convenient to all of the amenities of Wintergreen, a Four Season resort nestled next to the Blue Ridge Parkway in Nelson County. The house is less than 1 minute from the main resort and ski lifts. You can ski in/out by walking down our rear steps and between the houses behind us on Tyro slope. No need to drive and park at the resort.

There's plenty of drama in this house featuring the main floor great room with a whole house cathedral ceiling and wood stove. The completely rebuilt wrap around deck overlooks the Tyro slope and has fantastic mountain and valley views of Waynesboro and Crozet. Downstairs are 3 bedrooms all with new foam mattress beds (Queen/Queen/2 Twins) and linens. There is a cozy screen room off the master that also has mountain views. There is parking for three vehicles in the newly expanded parking pad out front, plus street parking behind the house on Tyro Lane.

There are two completely remodeled full baths, one includes a stacked front load high efficiency full sized washer and dryer. The gourmet kitchen is spacious and bright and has a stove, exhaust hood, refrigerator with an ice/water dispenser, microwave, dishwasher and disposal. There is a full set of dishes, utensils, and glasses to easily handle 6 guests.

Guest Reviews:

- "The Chalet was great. It reminded us of being in Paris. We loved the Ikea furniture, the heated floor and the hot tub. It was also nice to have an air controlled unit in each room. It was nice and cozy with great views. We thoroughly enjoyed our stay." - "Quintessential mountain cabin with modern interior styling and all the comforts of home. Highly recommended!" - "We thoroughly enjoyed our stay at Treeloft. The house was everything we needed! Definitely will return. Highly recommend."

Vacation Rentals in Wintergreen Resort
COZY SKI COTTAGE-SKI IN SKI OUT
House
Roseland, Virginia, USA

the cottage has large front and rear decks, stairway to slopes, nice furniture and bedding, fully equipped kitchen, sleeps 6 with 1 king, 1 queen, and 2 twin beds..2 flat screen TVs, wireless internet and cable, DVD player, washer/dryer, living room has wood burning fireplace with wood provided, off street parking, great privacy at end of street ...2 minute drive to restaurants and entertainment.

Guest Reviews:

- "The location is perfect. Six of us stayed for three nights and had a blast. Close to the Wintergreen amenities and perfectly located to the slopes." - "The house was very cute. Great location. The communication with the owner was awesome. We definitely rent again." - "Great stay for 2 grandparents, 2 parents, and 2 kids. Cozy cottage feel, but plenty of room. back porch is feet from lower tyro slope. slopeside with nice view, quiet street."

Vacation Rentals in Wintergreen Resort
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite!
House
Wintergreen Resort, Virginia, USA

This cozy, vintage cabin has been fully modernized and updated to ensure your total enjoyment. We designed each room for maximum efficiency and total comfort. Vaulted shiplap ceilings, exposed beams, four flat screen TVs, multiple charging stations, updated fixtures and luxury furnishings surround you.

The main level has an open concept kitchen, dining and living space. The kitchen is stocked with oils, spices, baking basics (even mountain-themed squirrel and bear cookie cutters!) and stainless steel appliances. The knives are sharp, pots are new, and if you'd rather spend your day on the hiking trails or slopes, the crockpot feeds a crowd. The dining table expands to seat 8, and the large, plush leather sofa in the living area is a great space to pile in for movie night. The stone wood-burning fireplace is available for your use, and we've included instructions that make it easy to have a crackling fire in no time (wood not incl). The BlueTooth surround sound system hooks to your phone with the touch of a button, and the house is stocked with books and games. We've even supplied a telescope for stargazing and wildlife spotting! It's easy to come in, curl up, and feel at home.

The two main floor bedrooms and spa inspired bathrooms are designed to help guests rest and recharge after active days on the mountain. The luxury memory foam mattresses are new and topped with plush velvet quilts and linen cotton duvets. There are plenty of pillows, lots of storage space, luggage racks, and at least 4 USB ports in each room. The Blue Ridge king bedroom has a gorgeous seasonal mountain view; there's nothing like seeing the colors of a sunrise peeking through the Blue Ridge. Of course, sleek new blackout shades and high powered ceiling and table top fans keep you cool and sleeping well past sunrise if that’s more your style. The Wintergreen king bedroom boasts local art and a dedicated work space.

The bathrooms brand new mountain spa inspired tile showers, heated tile floors, granite countertops and are stocked with luxury amenities, a first aid kit, hair dryers, and plenty of clean, fluffy towels. There is a washer and dryer in the cabin, with laundry soap supplied.

Outside you'll find a large deck with gorgeous seasonal mountain views and year round views of the Lower Tyro ski slope, just a few steps away. In the spring and summer, the mountains peek through the treetops, making this feel like your own private treehouse. Plush deck seating, a warm propane fire pit, and a sparkling brand new hot tub draw will make you want to spend all your time outside. A new Solo Pi Pizza oven and gas grill are provided for easy dinner prep. The deck dining table expands to seat a crowd, and the propane amenities turn on with the touch of a button. Easy dinners and all the ambiance and warmth of a fire with none of the work!

Part of the deck is covered, so you start your day with yoga in the summer (we provide mats) air sit by the fire and watch the snow fall in winter. The front of the home has an exterior ski closet and an EV charging outlet (please bring your own cord).

The third floor Wildflower Suite is a sleeping loft at the top of the spiral staircase. This brand new flex space can accommodate a couple, a family, teens or any other group of four. One queen bed and a daybed with a trundle ensure that everyone can be comfortable together. The room has two high powered fans, more USB ports than we can count, and individual reading lights, charging outlets, and storage shelves. The entertainment space has games, puzzles, a Roku TV, and a video game console stocked with vintage Nintendo games. It might be guests staying here to come down and join the rest of the group! The loft overlooks the main living area, and the opening can be closed with the sound and light blocking curtains.

This Treetop Chalet is a perfect getaway for couples seeking a cozy, romantic getaway, or friends and families making memories together.

Guests can walk from the Treetop Chalet to the Lower Tyro ski slope in less than one minute. That makes coming home for lunch during a busy day of skiing easy! It's that same distance to the hiking trail entrance. The location is perfect for families with lots of different activity and endurance levels! Park your car, avoid the crowded lodge and lines, and ski in and out as you like!

You'll access the home via a keyless entry touchpad. Your welcome and check in is contactless, for your safety and privacy. Parking is simple, three spots right in front of the home. No long walks lugging groceries or gear - the front door is 3 steps from the parking area. You'll have access to the full house, with the exception of the locked owner's closet and basement storage area.

The cabin, like most Wintergreen properties, does not have central air. It is typically 10-20 degrees cooler on the mountain than in the valley, and because of that, guests are usually very comfortable just opening the windows. There are two high powered fans in each room if you like it cooler.

This property is about 1230 square feet. It is designed to accommodate families, and is not well suited to groups of 8 adults. We're sad to say you will want to choose another property for your big girl or guy getaway. Plugging in all those hairdryers and running them at once will trip the circuit - trust us!

We're looking forward to welcoming you!

AREA INFORMATION
Wintergreen Resort is a four season resort nestled in the Blue Ridge Mountains. There's so much to do here! We're located less than an hour from Harrisonburg and Charlottesville, less than 2 hours from Richmond, and less than 3 hours from Northern Virginia.

We've grouped some of our favorite activities below as a sampling of what's available. When you book, we'll send you a full guest guide with more information so that you can plan the vacation you've been daydreaming about!

HIKING: Shenandoah National Park (direct access), Highlands Leisure Trail (1.3 miles), Upper Shamokin Falls Trail (4.4 miles), Appalachian Trail-Three Ridges Hike (4.6 miles), Ravens Roost Overlook (7.5 miles), Rock Point Overlook (7.9 miles), Humpback Rock (11.7 miles), Crabtree Falls (20.0 miles)

SIP + SAMPLE: Devil's Backbone Basecamp Brewpub (8.0 miles), Hill Top Berry Farm & Winery (13.0 miles), Wood Ridge Farm Brewery (20.0 miles), Seven Arrows Brewing Company (20.4 miles), Blue Mountain Brewery (21.0 miles), Veritas Vineyards and Winery (21.6 miles), Afton Mountain Vineyards (21.9 miles)

WINTERGREEN ACTIVITIES: Wintergreen Ski Resort (ski-in/ski-out access), Discovery Ridge Adventure Center, Wintergreen Adaptive Sports, Shamokin Springs Nature Preserve, The Plunge Snow Tubing Park, Stony Creek Golf Course, on-site dining, 30 miles of walking/hiking trails, panoramic viewing platform, zipline, treehouse, geocaching

ATTRACTIONS: Three Ridges Overlook, Blue Ridge Parkway (5.5 miles), Shenandoah National Park/Skyline Drive (20.8 miles), Oak Ridge Estate (27.2 miles), Chiles Peach and Apple Orchard (27.5 miles) Appomattox Court House National Historical Park (57.1 miles)

HISTORIC SITES: Frontier Culture Museum (28.6 miles), Woodrow Wilson Presidential Library & Museum (29.8 miles), Monticello (44.4 miles), James Monroe's Highland (46.7 miles), Poplar Forest (59.8 miles)

AIRPORT: Charlottesville-Albemarle Airport (47.3 miles)

Guest Reviews:

- "Great property! Very quiet and very clean. Host was very responsive and accommodating. Felt like a home away from home. Will definitely be back in the near future!" - "Easy check in. Great location. Kids loved the loft area!" - "House was very clean, had everything we needed to be comfortable, and very convenient to get to the slopes. Would definitely visit again. Thanks!" - "Although the weather conditions weren’t ideal, we still enjoyed our stay! The house was conveniently located and clean. There were plenty of games and puzzles to keep us busy. The owner communicates quickly and thoroughly. Would definitely recommend!"

Wintergreen Resort Family Friendly Vacation rentals

Wintergreen Resort Vacation rentals with Parking

Wintergreen Resort Vacation rentals with Entertainment

Wintergreen Resort Pet Friendly Vacation rentals

Wintergreen Resort Vacation rentals with Spa

Wintergreen Resort Vacation-Rentals on the Map

Compare the Best Vacation-Rentals in Wintergreen Resort – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Serene Hideaway with Views, 1 Mi to Hike and Ski! Wintergreen, VA, USA 384 3.0 9.0 3 Click here
Wintergreen Resort Home w/2 Decks + Ski Access! 115 Tyro Ln, Nellysford, VA, 22967, USA 279 3.0 1 Click here
Wintergreen Resort Home with 2 Decks and Ski Access! Roseland, VA, USA 344 3.0 9.0 1 Click here
Wintergreen Home w/Hot Tub, Deck & Mountain Views 26 Shagbark Lane, Nellysford, VA, 22967, USA 366 3.0 1 Click here
Wintergreen Home with Hot Tub, Deck and Mountain Views Wintergreen, VA, USA 450 3.0 8.0 1 Click here
Wintergreen Resort Home: Close to Slopes & Trails 76 Pedlars Point, Nellysford, VA, 22958, USA 390 3.0 1 Click here
Walk to Ski Slopes Wintergreen Resort Treehouse Beech Grove, VA, USA 305 3.0 1 Click here
Designer Home w\/ Fire Pit ~ 70 Steps to Slopes! 749 Pedlars Edge Dr, Nellysford, VA, 22967, USA 756 3.0 1 Click here
Bear Necessities with Wintergreen Advantage Wintergreen, VA, USA 431 3.0 1 Click here
Charming 4-bedroom home with WiFi, game room and more near Wintergreen Resort! Nellysford, Virginia, USA 327 2.0 10.0 6 Click here
Antlers Aweigh with Wintergreen Advantage Wintergreen, VA, USA 678 3.0 1 Click here
Pedlars Big Mountain Home at Wintergreen 564 Pedlars Point, Nellysford, VA, 22967, USA 422 2.0 1 Click here
Shangri-la ! A Perfect Getaway for everyone ! 27 Pedlars End, Beech Grove, VA, VA 22967, USA 276 10.0 2 Click here
Large and Luxurious Exec 5BR Chalet Wintergreen Resort, Virginia, USA 563 10.0 250 Click here
Wintergreen Home w/Hot Tub, Deck & Mountain Views Wintergreen, Virginia, USA 489 9.6 194 Click here
Beautiful Mountain Views, Steps to the slopes! wintergreen, Virginia, USA 388 10.0 141 Click here
Modern Mountain Retreat: Hot Tub, Chef's Kitchen, Game Room & Ski Access Nellysford, Virginia, USA 790 10.0 132 Click here
Remodeled 3BR/2BA Ski Chalet off Tyro Slope Roseland, Virginia, USA 316 9.8 106 Click here
COZY SKI COTTAGE-SKI IN SKI OUT Roseland, Virginia, USA 468 9.6 89 Click here
Modern Luxe Treetop Retreat-Hot Tub, Gas Fire Pit, Steps to Ski! Guest Favorite! Wintergreen Resort, Virginia, USA 451 10.0 65 Click here

Note: The prices for each Vacation-Rentals in Wintergreen Resort do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Vacation rentals in Wintergreen Resort that include a pool include:

  • Wintergreen Resort Home w/2 Decks + Ski Access!.- Review Count: 0, Rating: 0.0
  • Wintergreen Resort Home with 2 Decks and Ski Access!.- Review Count: 1, Rating: 9.0
  • Designer Home w\/ Fire Pit ~ 70 Steps to Slopes!.- Review Count: 0, Rating: 0.0

Vacation rentals in Wintergreen Resort offering shuttle or transport options include:

  • Wintergreen Home with Hot Tub, Deck and Mountain Views.- Review Count: 1, Rating: 8.0

These vacation rentals in Wintergreen Resort provide spa or wellness access:

  • Wintergreen Home with Hot Tub, Deck and Mountain Views.- Review Count: 1, Rating: 8.0

Family-friendly vacation rentals in Wintergreen Resort include:

  • Serene Hideaway with Views, 1 Mi to Hike and Ski!.- Review Count: 3, Rating: 9.0
  • Wintergreen Resort Home w/2 Decks + Ski Access!.- Review Count: 0, Rating: 0.0
  • Wintergreen Resort Home with 2 Decks and Ski Access!.- Review Count: 1, Rating: 9.0

Pet-friendly vacation rentals in Wintergreen Resort include:

  • Bear Necessities with Wintergreen Advantage.- Review Count: 0, Rating: 0.0
  • Beautiful Mountain Views, Steps to the slopes!.- Review Count: 141, Rating: 10.0
  • Modern Mountain Retreat: Hot Tub, Chef's Kitchen, Game Room & Ski Access.- Review Count: 132, Rating: 10.0

Vacation rentals in Wintergreen Resort with private or on-site parking include:

  • Serene Hideaway with Views, 1 Mi to Hike and Ski!.- Review Count: 3, Rating: 9.0
  • Wintergreen Resort Home w/2 Decks + Ski Access!.- Review Count: 0, Rating: 0.0
  • Wintergreen Resort Home with 2 Decks and Ski Access!.- Review Count: 1, Rating: 9.0

Some of the best Vacation Rentals in Wintergreen Resort are:

  • Serene Hideaway with Views, 1 Mi to Hike and Ski!.- Review Count: 3, Rating: 9.0
  • Wintergreen Resort Home with 2 Decks and Ski Access!.- Review Count: 1, Rating: 9.0
  • Wintergreen Home with Hot Tub, Deck and Mountain Views.- Review Count: 1, Rating: 8.0

Some of the popular Vacation Rentals in Wintergreen Resort are:

  • Large and Luxurious Exec 5BR Chalet.- Review Count: 250, Rating: 10.0
  • Wintergreen Home w/Hot Tub, Deck & Mountain Views.- Review Count: 194, Rating: 9.6
  • Beautiful Mountain Views, Steps to the slopes!.- Review Count: 141, Rating: 10.0