Wintergreen holiday homes

We found 925 holiday rentals — enter your dates for availability
Select from 224 houses, 316 flats and other holiday rentals to find the perfect place for your stay in Wintergreen. Holiday homes provide the best amenities for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. At the end of the day, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Wintergreen

Showing deals for:13 Nov - 20 Nov

Room
Interior
Exterior detail
Private kitchen
Exceptional
(82 reviews)

Three Ridges Haven- Devils Backbone Brewing Company

Roseland

25% off
NZ$8,289
for 7 nights, 1 room
NZ$1,184 per night
includes taxes & fees
Three Ridges Haven- Devils Backbone Brewing Company
Room
Living area
Private kitchen
Dining
Exceptional
(5 reviews)

Majestic Mtn Cabin w quick hiking & overlook access

Nellysford

8% off
NZ$4,293
for 7 nights, 1 chalet
NZ$613 per night
includes taxes & fees
Majestic Mtn Cabin w quick hiking & overlook access
The large kitchen is renovated and stocked for cooks of all levels
Beautiful views of the George Washington National Park outside the front door.
Sunny spacious living area off the kitchen, with large floor to ceiling windows.
Property grounds
Exceptional
(223 reviews)

Reconnect with family & friends at our large, private, stylish Wintergreen home

Nellysford

8% off
NZ$10,808
for 7 nights, 1 home
NZ$1,544 per night
includes taxes & fees
Reconnect with family & friends at our large, private, stylish Wintergreen home
Enjoy the view from the deck.
Enjoy some wine by the fire pit.
Dine on the screened in deck.
The kitchen features seating for two at the bar top.
Exceptional
(9 reviews)

Extreme privacy/Acreage/Hot Tub/Mountain Views/Central!!

Afton

8% off
NZ$8,201
for 7 nights, 1 home
NZ$1,172 per night
includes taxes & fees
Extreme privacy/Acreage/Hot Tub/Mountain Views/Central!!
Exterior
Interior
Interior
Room
Exceptional
(8 reviews)

Inn at the Woods: Updated Cabin w/Mountain Views

Afton

7% off
NZ$4,550
for 7 nights, 1 cabin
NZ$650 per night
includes taxes & fees
Inn at the Woods: Updated Cabin w/Mountain Views
Dining Room Table
58" flat screen, basic cable.  Living Room
Kitchen.  Open to dining area and living room.
Front of House
Exceptional
(111 reviews)

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

Nellysford

12% off
NZ$3,011
for 7 nights, 1 home
NZ$430 per night
includes taxes & fees
Wintergreen Family Retreat- Each Br With Its Own Sliding Doors To A Deck
Cozy Family Room with wood burning fireplace
Large hot tub comfortably accommodates 6 adults
Kitchen opens to great room
Enter into spacious great room
Exceptional
(32 reviews)

Mountain Season Lodge

Nellysford

12% off
NZ$8,563
for 7 nights, 1 room
NZ$1,223 per night
includes taxes & fees
Mountain Season Lodge
Interior
Exterior
Fire pit with accessories to use as grill
Private kitchen
Exceptional
(66 reviews)

Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA

Montebello

12% off
NZ$1,918
for 7 nights, 1 cabin
NZ$274 per night
includes taxes & fees
Beautiful new cabins mile off Blue Ridge Parkway in Montebello, VA
Living room - main floor
Dining area
Exterior
Interior
Exceptional
(32 reviews)

Beautiful Mountain House Close to the Slopes

Nellysford

8% off
NZ$6,434
for 7 nights, 1 home
NZ$919 per night
includes taxes & fees
Beautiful Mountain House Close to the Slopes
Living room with full views of valley & mountains.  Wood burning fireplace.
Wall-to-wall windows creating a backdrop of treetops & mountain views.
The kitchen opens directly to the living room with beautiful views.
Private well-lit walkway to your private entrance on home's main floor.
Exceptional
(56 reviews)

Spacious + Serene Mtn Top Escape, 4 En Suites

Nellysford

8% off
NZ$4,908
for 7 nights, 1 home
NZ$701 per night
includes taxes & fees
Spacious + Serene Mtn Top Escape, 4 En Suites
Our private home.
The propane fire pit provides intimacy and warmth!
The downstairs full bathroom with shower/tub combo and washer/dryer.
Enjoy a home cooked meal in our fully stocked kitchen.
Exceptional
(22 reviews)

Secluded 20+ Acre Retreat Near Brew & Wine Trails

Afton

7% off
NZ$3,454
for 7 nights, 1 home
NZ$493 per night
includes taxes & fees
Secluded 20+ Acre Retreat Near Brew & Wine Trails
Private kitchen
Exterior
Property grounds
Interior
Exceptional
(21 reviews)

New Blue RIdge Mountains Montebello, Virginia with stary stary skies

Montebello

12% off
NZ$1,918
for 7 nights, 1 cabin
NZ$274 per night
includes taxes & fees
New Blue RIdge Mountains Montebello, Virginia with stary stary skies
Property grounds
Exterior
Interior
Interior
Exceptional
(27 reviews)

5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries

Montebello

12% off
NZ$1,918
for 7 nights, 1 cabin
NZ$274 per night
includes taxes & fees
5 minutes to Blue Ridge Parkway, Crabtree Falls, hiking, wineries, breweries
Exterior
Living area
Dining
Private kitchen
Exceptional
(22 reviews)

Above the Clouds! Perfect Escape for Families!

Nellysford

11% off
NZ$5,011
for 7 nights, 1 home
NZ$716 per night
includes taxes & fees
Above the Clouds! Perfect Escape for Families!
Exterior detail
Private kitchen
Interior
Exterior
Exceptional
(61 reviews)

Rockfish Farmhouse - Home In the heart of The Rockfish Valley

Afton

8% off
NZ$4,369
for 7 nights, 1 home
NZ$624 per night
includes taxes & fees
Rockfish Farmhouse - Home In the heart of The Rockfish Valley
Dining Room
Outdoor spa tub
Property grounds
Property grounds
Exceptional
(111 reviews)

Remodeled 3BR/2BA Ski Chalet off Tyro Slope

Nellysford

7% off
NZ$2,993
for 7 nights, 1 home
NZ$428 per night
includes taxes & fees
Remodeled 3BR/2BA Ski Chalet off Tyro Slope
Room
Living area
Interior
Private kitchen
Exceptional
(9 reviews)

Unique Stay! Yurt with Mountain View, 1 min to Breweries & Hiking, 5 min to Lake

Roseland

12% off
NZ$2,235
for 7 nights, 1 cabin
NZ$319 per night
includes taxes & fees
Unique Stay! Yurt with Mountain View, 1 min to Breweries & Hiking, 5 min to Lake
Outside your Condo
Living area
Games room
Fully Equiped Kitchen
Exceptional
(129 reviews)

Eagles Court Slopeside Condo, Wifi, Walk to everything!

Nellysford

11% off
NZ$2,115
for 7 nights, 1 apartment
NZ$302 per night
includes taxes & fees
Eagles Court Slopeside Condo, Wifi, Walk to everything!
Drone view of Black Bear Lodge!
Let's go back outside!
Dining
Open plan living and flexible seating!
Exceptional
(34 reviews)

Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.

Nellysford

8% off
NZ$7,074
for 7 nights, 1 home
NZ$1,011 per night
includes taxes & fees
Luxury Black Bear Lodge: Stunning 4 Season Mountain Views! Perfect for Families.
Kitchen
Back deck
Pool
Living area
Exceptional
(111 reviews)

Family Friendly Mountain Home! Great Location on Devils Knob

Nellysford

8% off
NZ$4,179
for 7 nights, 1 home
NZ$597 per night
includes taxes & fees
Family Friendly Mountain Home! Great Location on Devils Knob
Interior
Dining
Living area
Top of the stairs
Exceptional
(59 reviews)

Spectacular mountain home perfect for multiple families! Just added deck firepit

Nellysford

8% off
NZ$3,900
for 7 nights, 1 home
NZ$557 per night
includes taxes & fees
Spectacular mountain home perfect for multiple families! Just added deck firepit
Living area
Living area
Dining
Private kitchen
Exceptional
(28 reviews)

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

Nellysford

12% off
NZ$3,557
for 7 nights, 1 home
NZ$508 per night
includes taxes & fees
Condo at Fairway Woods, perfect home base for ski season! ☃️🏂
Dining
Exterior
Pool
Only four steps on sidewalk from parking lot.
Exceptional
(88 reviews)

New listing- Five minute walk to slopes and village!

Nellysford

8% off
NZ$2,690
for 7 nights, 1 apartment
NZ$384 per night
includes taxes & fees
New listing- Five minute walk to slopes and village!
Living area
Terrace/patio
Living area
Private kitchen
Exceptional
(21 reviews)

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

Nellysford

8% off
NZ$3,594
for 7 nights, 1 home
NZ$513 per night
includes taxes & fees
Buck's Cabin: Cozy retreat with hot tub. Pet- & kid-friendly!
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why visit Wintergreen

  • Outdoor Adventure: Experience thrilling skiing, snowboarding, and hiking in the stunning Blue Ridge Mountains.
  • Cultural Heritage: Discover local museums and historic sites that showcase Wintergreen's rich history and heritage.
  • Family-Friendly Activities: Enjoy a variety of activities suitable for all ages, including warm springs and nature trails.
  • Scenic Beauty: Immerse yourself in the breathtaking landscapes and verdant forests that surround the area.
  • Relaxation and Tranquility: Unwind in a peaceful setting, perfect for a rejuvenating holiday escape.

Top attractions near Wintergreen

Wintergreen in Virginia offers a blend of cultural heritage and outdoor excitement. Visitors can explore museums, historic houses, and national state parks that highlight the region's rich history and natural beauty. Ideal for a ski, adventure, or sports holiday, Wintergreen provides a unique escape for travellers seeking a mix of cultural, outdoor, and adventure experiences, all wrapped in a charming setting.

  • Swannanoa Palace: Explore a historic house with rich cultural vibes, located 16km from Wintergreen. Its storied past and elegant architecture create a charming glimpse into the region's heritage.
  • Walton's Mountain Museum: Discover local history and cultural artefacts at this museum, 21km away. Its exhibits provide an insightful perspective on the area's artistic and cultural traditions.
  • Rockfish Gap Entrance Shenandoah: Experience outdoor adventures at this national state park, 18km from Wintergreen. The park offers stunning scenery and opportunities for hiking and exploration.

Things to do recommended for couples

For a memorable couple’s retreat in Wintergreen, Virginia, indulge in local adventures and intimate moments. Explore scenic trails, savour regional culinary delights, and share cosy evenings by the fire. Experience true romance in an enchanting setting.

Things to do recommended for families

Families can enjoy a scenic drive to Wintergreen Resort for skiing and snowboarding, or explore nature trails for hiking. Discover local charm with a taste of American culture, and make memories in an authentic mountain setting.

Things to do recommended for groups

Groups visiting Wintergreen can enjoy hiking the scenic trails of the Blue Ridge Mountains, tasting local wines at nearby vineyards, and experiencing thrilling activities like zip-lining or skiing in winter. Don’t miss a cozy evening by the fireplace sharing stories after a day of adventure.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Wintergreen

No matter if you're travelling with a group, with family, bringing your pets along, or seeking longer stays, be sure to apply the appropriate filters based on your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Wintergreen with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and more on Vrbo.
  • Traveling to Wintergreen with young kids: Travelling with young children can present its own set of challenges. It's important to prioritise their comfort and safety, along with amenities suitable for their age, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Wintergreen: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone, including your four-legged friend, feels comfortable and at home.
  • Planning for a long term stay visiting Wintergreen: If you're searching for holiday rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Wintergreen

Wintergreen, Virginia offers a unique blend of adventure and family-friendly charm. Explore the verdant forests and enjoy the warm springs within walking distance. The area is perfect for skiing and other sports, providing an exciting yet relaxing holiday experience. Whether you’re seeking urban vibes or the tranquility of the countryside, Wintergreen’s diverse attractions ensure a memorable visit.

  • Three Ridges Wilderness: Nestled a mere 8km from Wintergreen, Three Ridges Wilderness offers an exhilarating escape into nature. This stunning park is renowned for its breathtaking scenery and abundant outdoor activities, making it a haven for adventure seekers. Visitors can indulge in skiing at nearby resorts or explore the vast network of trails that wind through the picturesque forest and nature reserves. The area's natural beauty is complemented by its proximity to a national state park, perfect for those who wish to immerse themselves in the tranquillity of the wilderness.
  • Love: Located 10km from Wintergreen, the charming village of Love invites travellers to experience a delightful blend of adventure and outdoor activities. Known for its ski opportunities, the area boasts access to ski fields and resorts, making it an ideal spot for winter sports enthusiasts. Beyond skiing, visitors can relish the beauty of nearby lakes and national parks, offering a serene backdrop for hiking, fishing, or simply soaking in the natural surroundings.
  • Roseland: Situated 16km from Wintergreen, Roseland is a vibrant city that caters to adventure lovers and sports enthusiasts alike. The region is famed for its excellent skiing facilities, with multiple ski resorts and ski fields available for visitors to enjoy. Beyond the slopes, Roseland's proximity to stunning lakes and national parks provides ample opportunities for exploration and leisure activities, making it a perfect destination for those seeking both excitement and relaxation in nature.

Best time to go to Wintergreen

If you're planning a trip to Wintergreen, it's a good idea to check both the weather and property rates. The warmest month is July.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January33.4°F (0.8°C)Light RainMostly SunnyModerately High
February37.2°F (2.9°C)Light RainMostly SunnyModerately High
March44.6°F (7.0°C)Light RainMostly SunnyAverage
April54.9°F (12.7°C)Light RainMostly SunnyAverage
May64.0°F (17.8°C)Light RainMostly SunnyModerately Low
June72.1°F (22.3°C)Light RainMostly SunnyModerately Low
July76.6°F (24.8°C)Light RainMostly SunnyAverage
August74.3°F (23.5°C)Light RainMostly SunnyModerately Low
September68.0°F (20.0°C)Light RainMostly SunnyAverage
October56.8°F (13.8°C)Light RainMostly SunnyAverage
November44.8°F (7.1°C)Light RainMostly SunnyAverage
December38.5°F (3.6°C)Light RainMostly SunnyModerately High

Booking with Vrbo is a breeze

Are you keen to save on your next adventure? Being flexible with your travel dates can make a difference, as prices often fluctuate. Additionally, booking a longer stay can lead to substantial savings. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides you with a convenient area to plan new adventures, manage your ongoing arrangements, or review and organise your bookings. Your saved or booked properties are neatly categorised into Potential, Upcoming, or Current Trips. To check out your Trip Boards, please visit: https://www.bookabach.co.nz/trips.

**Based on Vrbo properties bookings.

Why people love visiting scenic Wintergreen

Enjoy the wineries and other features of Wintergreen. Travellers to this scenic city praise the mountain views, skiing and hiking. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Activities and attractions in and around Wintergreen

Are you hoping to find attractions to see during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Wintergreen has to offer. Here are some of the major attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Hill Top Berry Farm & Winery (3.1 mi / 4.9 km)
  • Wintergreen Resort (3.2 mi / 5.1 km)
  • Afton Mountain Vineyards (8.9 mi / 14.3 km)
  • Veritas Vineyard and Winery (9.5 mi / 15.4 km)
  • Lovingston Winery (11.5 mi / 18.5 km)
  • Pippin Hill Farm & Vineyards (14 mi / 22.6 km)

Exploring the natural landscape of Wintergreen

Whether you're an adventurous traveller or just want to appreciate the scenery, Wintergreen is a great place to get out in nature. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Humpback Rocks (5.3 mi / 8.5 km)
  • Sherando Lake Recreation Area (6.5 mi / 10.5 km)
  • Crabtree Falls (10.1 mi / 16.3 km)
  • Blue Ridge Parkway North Entrance (10.3 mi / 16.6 km)
  • Rockfish Gap Entrance Shenandoah (10.8 mi / 17.4 km)
  • Reids Gap Trailhead (4.8 mi / 7.8 km)

Seasonal weather averages in Wintergreen

Travellers enjoy Wintergreen for its skiing. If you've planned your trip around snowy activities, consider visiting in January, December, February or March, when snowfall averages 3 cm and temperatures average 4°C.

Travelling to and around Wintergreen

The nearest airport is in Weyers Cave, VA (SHD-Shenandoah Valley Regional), located 26.2 mi (42.1 km) from the city centre. If you can't find a flight that's convenient for your trip, you can also fly into Charlottesville, VA (CHO-Charlottesville-Albemarle), which is 30.3 mi (48.8 km) away.

Frequently asked questions

What is the best area to stay in Wintergreen when booking a holiday home?
Pedlars Edge is one of the more desired locations to book a holiday home in Wintergreen. Settle in here and enjoy all the privacy and convenience that comes with having a place all to yourself.
What is the most popular type of holiday home accommodation in Wintergreen?
Condos are the most popular type of holiday home in Wintergreen, according to our data. Even if you've got a different vision in mind, Bookabach has holiday homes in a variety of shapes and sizes. Explore our options to find your ideal match.
How much does it cost to rent a holiday home in Wintergreen?
Different factors affect how much you'll pay for a holiday home in Wintergreen, like the time of year, property type and length of stay. However, all of our holiday homes have one thing in common — exceptional value. Just enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Wintergreen?
The average price for a holiday home by the beach in Wintergreen depends on when you're travelling and the size and style of property you're looking for. Find prices easily on Bookabach by entering your travel dates. Then use the handy filters to choose the number of bedrooms and amenities important to you, like air conditioning, WiFi and a pool.
Are there pet-friendly holiday homes in Wintergreen?
Pack a travel bag and a bone for the pup in your life because Wintergreen has 378 properties that open their doors to pets. Let your furriest pal enjoy the family fun at one of our pet-friendly holiday homes on Bookabach. Simply enter your travel dates and destination, then check the "Pets allowed" filter box.
Can I rent a house with a pool in Wintergreen?
Tick the "pool" box in our handy filter tool and choose from 236 houses with private pools in Wintergreen on Bookabach. Morning dip, sunset soak or midnight swim? Leisure time is up to you when your Bookabach holiday home has its own swimming pool.
What are popular home amenities in Wintergreen?
Some of the most popular home amenities people look for in Wintergreen include tennis, a swimming pool and a garden. Whether you're holidaying with your besties, family or even pets, Bookabach holiday properties have the best amenities for beginning new traditions with the people you cherish the most.
Are there large group holiday homes in Wintergreen?
Wintergreen has 102 holiday homes that can accommodate 10 or more guests. These properties come with all the space you need to enjoy good times with friends and family.
Are there holiday homes in Wintergreen that welcome kids?
Gather your whole family for an epic adventure in Wintergreen at one of our 378 family-friendly holiday homes. Many of these stays come with conveniences that are great for getaways with the little ones, including kitchens, living rooms and swimming pools. Just click on the "Properties good for families" filter and choose your favourite option.
What are the top attractions for families in Wintergreen?
If you're craving some family-friendly entertainment close to the centre of Wintergreen, head over to Stoney Creek Golf Course.
Are there one-bedroom holiday homes in Wintergreen?
Wintergreen has 65 one-bedroom homes on offer. Usually situated in desirable areas thanks to their compact size, a one-bedroom property is great if you're travelling with a friend or your partner. And with plenty of home comforts like full kitchens and more privacy than a standard hotel, you'll be able to kick back while exploring this fabulous destination.
Can I find two-bedroom holiday homes in Wintergreen?
Pick from 82 two-bedroom holiday homes in Wintergreen. Put your little ones in the second room or fill it with a couple of your favourite people. There's ample space for whoever's fortunate enough to be coming along for the ride.
Are there holiday homes with WiFi in Wintergreen?
Wintergreen has 149 holiday homes with WiFi, so you'll be able to stay connected while you're travelling. Simply check the "WiFi" box in our handy search filter to find the perfect property. From streaming movies with your family to writing and sending emails, these Bookabach homes make it a cinch to get online.
How can I find holiday homes with air conditioning in Wintergreen?
Decide on your travel dates and then use the filters to look for holiday homes with ac in Wintergreen on Bookabach. With 334 air-conditioned properties on offer here, you can enjoy a cool and comfy break.
How old do you have to be to rent a holiday home in Wintergreen?
It's a good idea to check with the Wintergreen holiday home you're looking at on Bookabach as the minimum age differs. However, it's normally 16, 18 or 21.
How long can I rent a holiday home in Wintergreen for?
It really depends on the Wintergreen property. To see all available options offering extended stays, simply type your travel dates and guest number into the Bookabach search page. Enjoy having the property to yourself, along with the comforts of home like a kitchen, air conditioning and an outdoor space where the kids can burn off energy. Be on the lookout for long-term stays that offer weekly or monthly discounts.

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