Photo by Rebecca Brent

Wintergreen Holiday Rentals

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Holiday Rentals in Wintergreen

Terrace/patio
SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
9.6 out of 10, Exceptional, (264)
"We had a great time. The house was comfortable and the area is beautiful! The only issues we had were a humming of the fan in the master bedroom upstairs, the door lock didn’t work for us (but the owners helped with this and all was well), and we had a hard time finding where to dump trash. The hot tub was wonderful, the wifi works great (we had one doing online school and one work), and all was just as the listing described. It was a great place to stay for a Liberty University graduation. If...
The price is NZ$661
per night
4 Jun - 5 Jun
SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV Cozy 4BR House.
Outdoor dining
Best views on Mountain! Breathtaking 5 Star. Open March weekends! BOOK NOW!
10.0 out of 10, Exceptional, (207)
"Property was everything advertised. Owner is the best! Stay with confidence...."
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, (272)
"We thoroughly enjoyed our stay at this condo. Quiet neighborhood and very comfortable. Appreciated all the basics offered that other rentals do not such as soap, garbage bags, toilet paper. But the owners went above that and had lotions, specialty soaps, cleaning supplies etc. Well stocked kitchen for cooking. While it was just the two of us we liked that there were games available for families and there was a nook upstairs for kids to get away. Highly recommend and would definitely come visit...
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
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Living area
Walk to Mtn Inn & The Market
9.6 out of 10, Exceptional, (19)
"It was nice. We discovered that the property was for sale which might have caused the kitchen to be short on utensils. We prefer to cook most meals when vacationing due to individual diets. Otherwise, allwas ok and I would feelfree to recommend it. Ann"
Walk to Mtn Inn & The Market
Private kitchen
Ski-In/Ski-Out Comfy Condo
10.0 out of 10, Exceptional, (10)
"Awesome condo very convenient if you are skiing."
Ski-In/Ski-Out Comfy Condo
Fridge, microwave, oven, stovetop
Fantastic Mountain & Valley Views! On Top of the Mountain & Close to the Resort.
9.8 out of 10, Exceptional, (163)
"This is a gorgeous property. The view is amazing. There is ample room for multiple families. The quiet road is perfect for taking a walk. It was a lovely location for our family to enjoy a long weekend."
Fantastic Mountain & Valley Views! On Top of the Mountain & Close to the Resort.
Property grounds
Luxury Chalet, Best Views in Virginia
10.0 out of 10, Exceptional, (25)
"We had a fabulous time at Blackrock Manor to celebrate a 90th birthday. The house works well for an elderly person as no steps are required to enter the house and the primary bedroom is located on the main level. The house is very nice, beautifully decorated, nicely equipped but the real show stopper are the views from the huge rear decks! Absolutely stunning!"
Luxury Chalet, Best Views in Virginia
Property grounds
Pine Cottage: Hot Tub and Central to Nelson 151
10.0 out of 10, Exceptional, (14)
"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 NZ$783
per night
12 Jun - 13 Jun
Pine Cottage: Hot Tub and Central to Nelson 151
Golf
Blue Ridge Mountain Retreat in Wintergreen
9.2 out of 10, Wonderful, (59)
"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
Property grounds
Travelers' Rest--Your Wintergreen Retreat in the Center of it All!
9.8 out of 10, Exceptional, (11)
"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!
Outdoor dining
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
10.0 out of 10, Exceptional, (107)
"There was an issue upon arrival, however the owners stepped right up to fix it. The house is very comfortable for 4 adults and 2 children. My only difficulty was the outside stairs. For an older couple the coolers were very heavy when we made it to the top :-) All in all, we had an enjoyable stay. Be alert as we had our truck broken into by a bear. No damage done, but a lesson learned."
Custom Builder just completely remodeled this Mountain Chalet! ...with Hot Tub!
Standard Suite | Private kitchen
Valley Extended Suites
3.0 star property
9.0 out of 10, Wonderful, (150)
"We loved the scenic drive to the property traveling from East on 64. "
The price is NZ$185
per night
4 Jun - 5 Jun
Valley Extended Suites
Exterior
Virginia Mountain Get Away Cabin...Hunt Fish Hike Bike
10.0 out of 10, Exceptional, (26)
"This spot comes with a breath-taking vista and was very well designed for comfort and privacy. Highly recommended and we hope to return!"
Virginia Mountain Get Away Cabin...Hunt Fish Hike Bike
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
9.0 out of 10, Wonderful, (236)
"We enjoyed our stay at your condo, especially the view. Just wanted to let you know that the remote for the dvd player needs batteries and the coffee maker didn’t work properly. The coffee didn’t flow out right and it overflowed. Other than that, everything was as described. We hope to stay at your beautiful condo again."
The price is NZ$360
per night
29 May - 30 May
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Fridge, microwave, oven, stovetop
5 Bedroom Hilltop Villa with Hot Tub and Magnificent Views
9.8 out of 10, Exceptional, (19)
"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
Dining
Restored Double Log Cabin on 400 Mountain Acres
10.0 out of 10, Exceptional, (217)
"Susan's place was a perfect place for me to gather with my children, their significant others, and grandchildren. The house was as advertised! it was secluded and quiet and the kitchen came fully appointed with pots, pans, utensils, plates, silverware, you name it. We cooked all our meals at the house and had everything we needed. Thank you Susan for letting us stay in your peaceful, mountain cabin."
Restored Double Log Cabin on 400 Mountain Acres
Property grounds
Cozy Country small two bedroom home.
10.0 out of 10, Exceptional, (7)
"What we needed, close to all, will be back. REG"
The price is NZ$396
per night
1 Jun - 2 Jun
Cozy Country small two bedroom home.
Fridge, microwave, oven, stovetop
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging
10.0 out of 10, Exceptional, (181)
"Our family really enjoyed this beautiful get away home! It has everything you need and more. They are already talking about going back again."
Secluded 150 Acre Property, Private Lakes, 360 Mountain Views, Elegant Lodging
Exterior
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
10.0 out of 10, Exceptional, (220)
"Bill and Cynthia are such amazing hosts and the property inside and out exemplifies it. What a great place to stay for some serious rural R&R! The property was very clean. They have thought of everything one would need for a delightful get away. If you forgot anything, just ask and they are sure to help one way or another. The Fresh eggs, courtesy of their chickens, were a treat and the farm animals are such fun…esp Posy, Zoey and Hemingway. We hope to return soon for a longer retreat! Thank you...
Farm Experience-In the Heart of Vineyard, Wine and Wedding Country-Spacious
Smart TV, fireplace, DVD player, books
View from the Top
10.0 out of 10, Exceptional, (37)
"First time at Wintergreen - condos are show their age in places, but I had a great time and the views were out of this world. Good hiking. Waterfalls. Cut through to Blue Ridge Parkway from the neighborhood allowed for great biking without having to descend/ascend the long road up from the entrance."
View from the Top
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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.

Other types of properties in Wintergreen you may be interested in

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wintergreen holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wintergreen. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wintergreen. Seeing all the best attractions is bound to make you fall in love with Wintergreen. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wintergreen short-term rentals, that won’t be hard to do.

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?

SNOW! Hot Tub! FAST WiFi, Firepit! Hiking off Property! 60" HDTV 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 51 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.

Recent reviews of Wintergreen properties
Expedia verified reviews