Wintergreen Vacation Rentals from ￥33,916: Search Short-Term Rentals

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

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14 : Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Wintergreen are Theater Room, Fooseball, Firepit, Mountains! and Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill .

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Our top choices for Wintergreen vacation rentals

1. Where the Trail Ends

Wintergreen Resort

Diana J.

￥30,575 total

includes taxes & fees

Aug 26 - Aug 27

2. Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

Roseland

Danielle B.

￥33,916 total

includes taxes & fees

Aug 26 - Aug 27

3. New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Roseland

Michelle

￥39,806 total

includes taxes & fees

Aug 26 - Aug 27

4. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Resort

Scott M.

￥43,349 total

includes taxes & fees

Aug 26 - Aug 27

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

Wintergreen Resort

Jennifer D.

￥41,074 total

includes taxes & fees

Aug 26 - Aug 27

Coffee/tea maker, fridge, microwave, oven

6. Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

Wintergreen Resort

Jennifer H.

￥49,714 total

includes taxes & fees

Aug 26 - Aug 27

1 bedroom, iron/ironing board, WiFi (free), bed sheets

7. First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Wintergreen Resort

Alicia K.

￥40,499 total

includes taxes & fees

Aug 31 - Sep 1

Cabin, Private Bathroom (Bear Tracks Cottage) | Exterior

8. Bear Tracks Cottage

Nellysford

￥64,796 total

includes taxes & fees

Sep 1 - Sep 2

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Top Wintergreen Hotel Reviews

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

10/10 Excellent

"Overall it was a quiet wintergreen summer experience. Close to the market and inn though we didn’t use either on the trip. Kitchen had the basics but don’t plan to prep anything complicated."

Walk to Slopes, Village & Market. Pool, Dog-Friendly, Bonus Kids Room, Fireplace

10/10 Excellent

"Lovely place. Warm and welcoming. Clean. Cozy. Nicely decorated and comfortably furnished. Beautiful views out of every window. Kitchen well laid out and well supplied. Good coffeemaker with both drip-to-carafe and K-cup options. Comfortable beds. Fantastic classical reading and music options on the shelves. Many places to be together in a group as well as quiet nooks to curl up and read or otherwise retreat. Easy access (short walks) to pool and market. For a summer visit, air conditioning works well and many well placed ceiling fans help keep temperature even throughout."

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

10/10 Excellent

"We had a great stay! This place has all we could need. We were able to cook what we wanted with ease. We appreciated having a real coffee maker and not just a Keurig. Loved that it was pet friendly. I had a question for the owner and received a very quick response which was greatly appreciated. Overall, would recommend!"

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

10/10 Excellent

"Our 2-BR condo was lovely. Everything was sparkling clean and the place was spacious for what we needed. What MADE it, though, was the VIEW which was spectacular! I felt we should have been pre-informed that there was no coffee for us to use. We could have easily brought some but didn’t know of its non-existence."

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."

Find out more about Wintergreen

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Frequently asked questions

Can I find vacation rentals in Wintergreen?

Yes, there are vacation rentals close to the most popular points of interest in Wintergreen, or you can select a secluded option if you'd like a relaxing place to stay. Discover why Wintergreen is known for its ski slopes and mountain landscape. Make sure you have time to check out the wineries and coffeehouses during your trip.

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

Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a hot tub. Some other top choices in Wintergreen are Theater Room, Fooseball, Firepit, Mountains! and Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill.

How many vacation rentals are there in Wintergreen?

Choose from 227 Expedia vacation rentals in Wintergreen for a memorable vacation.

What can I see and do in Wintergreen?

While you're exploring the area, George Washington National Forest and Sherando Lake Recreation Area are a couple of picturesque spots to get outside and enjoy nature. While here, Bold Rock Hard Cider Nellysford Cidery and Wintergreen Resort are other places worth a visit.

What’s a vacation rental in Wintergreen like?

A vacation rental is a private property where you can stay for several days or longer in Wintergreen. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a popular option for a family trip.

Wintergreen Vacation Rentals

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Check prices for these dates

Our top choices for Wintergreen vacation rentals

1. Where the Trail Ends

2. Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

3. New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

4. Wintergreen Condo -Steps to Ski and restaurants

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

6. Enjoy breweries, wineries, hikes & music · Short walk to the resort and dining!

7. First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

8. Bear Tracks Cottage

9. First Floor Slope Side Wintergreen Condo – Ski In / Ski Out

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

11. Spacious + Serene Mtn Top Escape, 4 En Suites

12. 2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

13. Panoramic Peak: Wintergreen Condo with Views

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

15. Cozy Lux Condo at Wintergreen Resort

16. Mountain Retreat in Wintergreen!

17. Pet-Friendly Retreat Walk to Slopes & Village!

18. Mountain View Vista: Resort Condo w/ Views

19. Walk to Slopes, Village & Market. Pool, Dog-Friendly, Bonus Kids Room, Fireplace

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

Find vacation rentals that suit your style

Top Wintergreen Hotel Reviews

Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!

Find out more about Wintergreen

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