Photo by Rebecca Brent

Wintergreen Holiday Rentals

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Holiday Rentals in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
9.6 out of 10, Exceptional, 268 reviews
"Only complaint i have is not enough air conditioning in the cabin other than that it was a great place to visit nice views quiet park"
The price is AU$640
per night
14 July - 15 July
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
10.0 out of 10, Exceptional, 209 reviews
"This is at least the third time we have stayed in this condo unit in the last two years. There is a reason we keep coming back; it is absolutely beautiful, both the accommodations and Mountain Views. I highly recommend!"
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, 274 reviews
"The condo was well furnished with everything you needed. Beds were comfortable and bathrooms clean. Great location close to the Mountain Inn. Would definitely stay here again!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
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Walk to Mtn Inn & The Market
9.4 out of 10, Exceptional, 22 reviews
"I came to town for a wedding and wish I'd had more time to spend. The resort itself is great, with lots of hiking spots and dining options, surrounded by trees and nature. The condo is adorable - even better than the pictures. I definitely hope to come back again!"
Walk to Mtn Inn & The Market
Ski-In/Ski-Out Comfy Condo
10.0 out of 10, Exceptional, 14 reviews
"This property was perfect for us to getaway for a long weekend. Beautiful setting and everything we needed was walkable. The condo had everything we needed and our host was so responsive!"
Ski-In/Ski-Out Comfy Condo
Fantastic Mountain & Valley Views! On Top of the Mountain & Close to the Resort.
9.8 out of 10, Exceptional, 164 reviews
"The house is very cute and clean, the mountains view is stunning!"
Fantastic Mountain & Valley Views! On Top of the Mountain & Close to the Resort.
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
9.8 out of 10, Exceptional, 11 reviews
"We enjoyed our stay at Travelers' Rest but I think the listing should mention that the upstairs bedroom is a loft and open to the LR (which did not work with an early rising infant). Also, and I should know by now, the photos make the living area look bigger than it is. That said, it is wonderfully situated at end of cul de sac but close to lodge and market. The view is spectacular and it is very well equipped."
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
Luxury Chalet, Best Views in Virginia
9.8 out of 10, Exceptional, 26 reviews
"We particularly enjoyed the spectacular views. Beds were comfy. Found the decor a bit overdone. Lighting was hard to figure out (especially since we were directed to keep outside lighting at a minimum.) Master toilet didn't work (sent message to property manager). One bedroom on mid-level did not have a bathroom access (found that to be a little strange) and not represented in information about the house. Hot water not working in one of the kitchen sinks and took forever to get hot in the other...
Luxury Chalet, Best Views in Virginia
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
10.0 out of 10, Exceptional, 108 reviews
"My family loves this home and we have stayed multiple times. Could not be happier to come back."
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Pine Cottage: Hot Tub and Central to Nelson 151
10.0 out of 10, Exceptional, 14 reviews
"Need to step back and regroup and refresh and the cottage was perfect. Quiet, hot tub under the stars and a good night sleep was what the dr ordered !! Thank you!!"
The price is AU$717
per night
15 July - 16 July
Pine Cottage: Hot Tub and Central to Nelson 151
Blue Ridge Mountain Retreat in Wintergreen
9.2 out of 10, Wonderful, 59 reviews
"I brought a group of 20 youth and adults for a church ski retreat. The house was comfortable, fully stocked with the necessities and easily accessible to Wintergreen"
Blue Ridge Mountain Retreat in Wintergreen
Valley Extended Suites
3.0 star property
9.0 out of 10, Wonderful, 153 reviews
"We loved the scenic drive to the property traveling from East on 64. "
The price is AU$164
per night
7 July - 8 July
Valley Extended Suites
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, 240 reviews
"Great spot for a long weekend away. The space was perfect for our family of three and dog and the view was outstanding. Have already booked again for next Memorial Day weekend!"
The price is AU$339
per night
15 July - 16 July
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Virginia Mountain Get Away Cabin...Hunt Fish Hike Bike
10.0 out of 10, Exceptional, 30 reviews
"It was a great place to forget about the real world and relax! Hosts were responsive and it was a clean and inviting cabin!"
Virginia Mountain Get Away Cabin...Hunt Fish Hike Bike
Restored Double Log Cabin on 400 Mountain Acres
10.0 out of 10, Exceptional, 219 reviews
"The property was nestled in the woods, with plenty to do in the surrounding area! The house was stocked with everything you could possibly need. It was beautifully decorated, charming, and exceptionally clean!l Our family would definitely visit here again!"
Restored Double Log Cabin on 400 Mountain Acres
5 Bedroom Hilltop Villa with Hot Tub and Magnificent Views
9.8 out of 10, Exceptional, 19 reviews
"We had a fantastic time! House accommodations were exceptional. Very secluded. All needs were met. Would definitely do it again."
5 Bedroom Hilltop Villa with Hot Tub and Magnificent Views
Cozy Country small two bedroom home.
10.0 out of 10, Exceptional, 7 reviews
"What we needed, close to all, will be back. REG"
The price is AU$378
per night
8 July - 9 July
Cozy Country small two bedroom home.
Ivy Rose Cottage nestled b/t Cville & Vineyards
10.0 out of 10, Exceptional, 18 reviews
"Really enjoyed our stay."
The price is AU$570
per night
1 July - 2 July
Ivy Rose Cottage nestled b/t Cville & Vineyards
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging
10.0 out of 10, Exceptional, 183 reviews
"Great place to stay and have my wedding! Would definitely come back for an anniversary stay!"
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging
View from the Top
10.0 out of 10, Exceptional, 38 reviews
"Beautiful condo that is definitely over the top in accommodations. One of my favorite places to stay at wintergreen."
View from the Top
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See all available properties in Wintergreen
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Wintergreen Holiday Home Travel Info

Other types of properties in Wintergreen you may be interested in

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
9.6 out of 10, Exceptional, 268 reviews
"Only complaint i have is not enough air conditioning in the cabin other than that it was a great place to visit nice views quiet park"
The price is AU$640
per night
14 July - 15 July
Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
10.0 out of 10, Exceptional, 209 reviews
"This is at least the third time we have stayed in this condo unit in the last two years. There is a reason we keep coming back; it is absolutely beautiful, both the accommodations and Mountain Views. I highly recommend!"
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
10.0 out of 10, Exceptional, 274 reviews
"The condo was well furnished with everything you needed. Beds were comfortable and bathrooms clean. Great location close to the Mountain Inn. Would definitely stay here again!"
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Everything you need to know about Wintergreen holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wintergreen holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Wintergreen holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wintergreen. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wintergreen holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wintergreen holiday rentals we have selected for you start as low as AU$164 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Wintergreen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wintergreen holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wintergreen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find holiday rentals in Wintergreen?

Yes, there are holiday rentals close to the most popular sights in Wintergreen, or you can select a more secluded option if you're looking for a relaxing stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffee shops during your trip.

What are some of the best holiday rentals that Wintergreen has to offer?

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.: This highly rated holiday home rental in Wintergreen is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Our travellers also rate Fantastic Mountain & Valley Views! On Top of the Mountain & Close to the Resort. as a favourite home for rent in Wintergreen.

How many holiday rentals are there in Wintergreen?

Choose from 48 Expedia holiday rentals in Wintergreen for a memorable holiday.

What can I see and do in Wintergreen?

While exploring the area, visit family-friendly sights like War Fields, or get outside and enjoy nature at George Washington National Forest. Wintergreen Resort and Bold Rock Hard Cider Nellysford Cidery are a couple of places you'll find in the wider area.

What’s a holiday rental in Wintergreen like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Wintergreen. Holiday rentals feature amenities such as hot tubs, fire pits and patios so your stay will be comfortable. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and busy reception areas while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a family getaway.

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