Photo by Rebecca Brent

Wintergreen holiday homes

We found 831 holiday rentals — enter your dates for availability

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April 2025

May 2025

Select from 47 houses, 147 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:18 Jul - 25 Jul

Exceptional

(6 reviews)

Charming 5 Bedroom Historic brick home w/ sprawling river views, pool & hot tub!

Waynesboro, VA

8% off

NZ$2,635 per night

includes taxes & fees

Exceptional

(44 reviews)

Quiet farmhouse with pond, trails, hot tub, close to skiing and breweries

Roseland, VA

16% off

NZ$886 per night

includes taxes & fees

Exceptional

(9 reviews)

Mountain Escape: updated kitchen, king bed, walk to nature center, pet friendly

Nellysford, VA

7% off

NZ$488 per night

includes taxes & fees

Exceptional

(23 reviews)

Fulton Belle Vue - Beautiful fully renovated Farmhouse in Afton-great location.

Afton, VA

8% off

NZ$1,116 per night

includes taxes & fees

Exceptional

(14 reviews)

Cottage with stream, mountains, peaceful, quite, secluded, dog friendly.

Tyro, VA

8% off

NZ$353 per night

includes taxes & fees

Exceptional

(107 reviews)

Blue Ridge Mountains, Hiking, Skiing, Fishing, Mountain Air, Breweries, Wineries

Roseland, VA

8% off

NZ$335 per night

includes taxes & fees

Exceptional

(57 reviews)

Spectacular mountain home perfect for multiple families! Just added '80s arcade!

Nellysford, VA

7% off

NZ$568 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Wintergreen

Fresh Private Hot Tub Lower Deck
Relaxing Location in woods with Beautiful Views

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

Sleeps 11 · 4 bedrooms · 2 bathrooms

Good morning! Spectacular sunrise from the living room and deck!

Best views on Mountain! Breathtaking 5 Star. FLASH SALE! April 4-6 ONLY! 150 nt!

Sleeps 6 · 2 bedrooms · 2 bathrooms

Stone Patio, Adirondack Chairs, Fire Pit & Amazing Views of Mountains and Valley

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

Sleeps 14 · 5 bedrooms · 2 bathrooms

Family room has lots of space for movies or XBox

Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK

Sleeps 11 · 4 bedrooms · 2 bathrooms

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 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:

Stoney Creek Golf Course (1.3 mi / 2.1 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)
Pippin Hill Farm & Vineyards (14 mi / 22.6 km)
King Family Vineyards (15.4 mi / 24.7 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:

Sherando Lake Recreation Area (6.8 mi / 10.9 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)
Humpback Rocks (5.3 mi / 8.5 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.