Wintergreen Holiday Rentals: Short-Term Accommodations for Rent

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

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 : This highly rated holiday home rental in Wintergreen is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 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. Some other top choices in Wintergreen are Theater Room, Fooseball, Firepit, Mountains! and Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort! .

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Our top choices for Wintergreen holiday rentals

1. Wintergreen. Panoramic Sunsets, Mountain Views, Pool, 2 King Suites, 99 midweek

Wintergreen Resort

Chrissy R.

HK$2,093 total

includes taxes & fees

17 Aug - 18 Aug

2. Blackwood Chalet

Nellysford

Toni

HK$3,252 total

includes taxes & fees

16 Aug - 17 Aug

3. Overlook 08 with Wintergreen Advantage

Wintergreen

Jason

HK$3,982 total

includes taxes & fees

13 Sept - 14 Sept

4. Endless Mountain Top Views from All The Way Up!

Wintergreen Resort

Jennifer P.

HK$2,262 total

includes taxes & fees

18 Aug - 19 Aug

5. Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

Wintergreen Resort

Stanley W.

HK$2,816 total

includes taxes & fees

31 Aug - 1 Sept

6. Serenity Cabin-Woodland Retreat

Wintergreen Resort

Annamarie P.

HK$3,651 total

includes taxes & fees

24 Aug - 25 Aug

7. Escape to the Blue Ridge Mountains at Wine-tergreen!

Wintergreen Resort

Jennifer D.

HK$2,028 total

includes taxes & fees

16 Aug - 17 Aug

8. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Resort

Scott M.

HK$2,140 total

includes taxes & fees

18 Aug - 19 Aug

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Top Wintergreen Hotel Reviews

Wintergreen Luxury, Best Views in VA!

10/10 Excellent

"House was great for our family vacation. An actual million dollar view. Family had a wonderful week enjoying the surrounding area with hiking, fishing and local distilleries.House is very well appointed and our host Aubrey was excellent with communication before and during our trip. One tip- Definitely suggest bringing as much food supply as possible to save some driving time to store."

New Build! Log Cabin with Hot Tub in Wintergreen

10/10 Excellent

"Our family had a wonderful time during our stay at Chestnut Springs. The home is beautiful and nestled in the hills. There was plenty of room for six adults and five kids ages eight to sixteen. The hot tub was a big hit as was the comfortable furnishings and the wood burning fireplace. The kitchen is well stocked with cookware and dinnerware.Our host was very pleasant and quick to respond via email to my questions.We all enjoyed nearby Lake Monocan located at the Stoney Creek area of Wintergreen. We also enjoyed the two breweries/restaurants in nearby Nellyville.A great time was had by all!"

Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

10/10 Excellent

"Beautiful condo close to the Mountain Inn. Kitchen is well stocked and the owners provide a lot for your furry companions. We had a great time hiking the trails and coming back for a quiet evening. Wonderful place to stay and I can't wait to come back!!"

Endless Mountain Top Views from All The Way Up!

10/10 Excellent

"If I could rate it higher I would! Stayed here as a Basecamp for a hiking trip with my kids. We couldn't believe our eyes upon entering, the view was incredible. All of the beds were so comfortable as well as the rest of the furniture. The kitchen had plenty of coffee and all of the fixings ready to go. It also had all the utensils I needed to cook for everyone. The kids and I were able to get on our favorite streaming services to relax. They had detergent and dryer sheets and anything else I forgot. The communication was great. Responded within 30 mins. First class all the way. Plan on coming back!"

Find out more about Wintergreen

Search for holiday rentals in Wintergreen on Expedia! You can easily find your home rentals, villas, holiday apartments in Wintergreen using one of the methods below:

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Look no further and take a look at our great range of rental properties in Wintergreen!

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?

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14: This highly rated holiday home rental in Wintergreen is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 5 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. Some other top choices in Wintergreen are Theater Room, Fooseball, Firepit, Mountains! and Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!.

How many holiday rentals are there in Wintergreen?

Choose from 224 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. While here, Bold Rock Hard Cider Nellysford Cidery and Wintergreen Resort are other places worth a visit.

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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Our top choices for Wintergreen holiday rentals