Wintergreen Vacation Rentals from ￥34,158: 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 Walk to Slope-Tyro/Luxury Living/Sunset Mountain Views and Same Day Arrival OK .

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In two weeks

In two months

In three months

In four months

Our top choices for Wintergreen vacation rentals

1. Where the Trail Ends

Wintergreen Resort

Diana J.

￥28,166 total

includes taxes & fees

Sep 9 - Sep 10

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

Roseland

Deborah R.

￥34,158 total

includes taxes & fees

Sep 1 - Sep 2

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

Roseland

Michelle

￥40,091 total

includes taxes & fees

Sep 1 - Sep 2

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

Wintergreen Resort

Jennifer P.

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

Wintergreen Resort

Alicia K.

￥39,982 total

includes taxes & fees

Sep 9 - Sep 10

6. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Resort

Scott M.

￥42,968 total

includes taxes & fees

Sep 1 - Sep 2

7. Labor Day SPECIAL!!! Stay two and the third night for half price!

Wintergreen Resort

Jennifer D.

￥41,368 total

includes taxes & fees

Sep 1 - Sep 2

8. "Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

Wintergreen Resort

Jennifer H.

￥50,071 total

includes taxes & fees

Sep 1 - Sep 2

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Top Wintergreen Hotel Reviews

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

10/10 Excellent

"Just wrapped up a fantastic 3-night stay with my husband and our dog—this place is a total gem! Spacious, spotless, comfy, and truly pet-welcoming with everything you would need including thoughtful touches for the fur baby. We loved the king bed (so comfy!), and cozy fireplace for our surprisingly chilly August nights. You can tell the owner really cares for this place, and it shows in every detail—from the decor, entertainment options, furnishings and more, to the well-stocked kitchen. Also, the location within Wintergreen Resort is ideal. Heather, our host, was super responsive and a real pleasure to rent from. You'd be hard-pressed to find a better place or host."

Newly Built Designer Home in Wintergreen

10/10 Excellent

"This is one of the finest properties we've ever visited in all of our trips to Wintergreen. We have been coming since 1978. The location is great. It's snuggled into the lower elevations of the resort. That will pay dividends during your stay. Less vehicular and foot traffic. Combine that with easy access to the Appalachian Trail for some of the best hiking and views in the Blue Ridge. Ideal for kids and pets.The property itself? Beautiful, clean, tasteful, accommodating. The lighting and furnishings are designer quality. The well stocked kitchen is a joy to use with all of the necessary gadgets and utensils. Prefer pour over coffee? Your goose neck kettle is waiting. More of a French press kind of person? The Fellow Clara press is ready to go.The bedrooms and bathrooms are beautifully appointed. The wifi and entertainment setup are top drawer. You will not be disappointed. Highly recommended!"

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."

Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill

10/10 Excellent

"Great house in a great location. Wonderful getaway for our three generation family vacation (ages 13-85 plus a dog). We really loved the deck, fire pit and hot tub plus the nearby nature trail loop. Cooking for our crowd was easy, and there were multiple places for different groups to hang out. The weather was too wet to do as much outdoors as we wanted but there were lots of things to keep us busy in the house (puzzles, movies, baking, hot tub, games). Highly recommend this great house in Wintergreen Resort."

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

How many vacation rentals are there in Wintergreen?

Choose from 229 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.

Room 1

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. Endless Mountain Top Views from All The Way Up!

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

6. Wintergreen Condo -Steps to Ski and restaurants

7. Labor Day SPECIAL!!! Stay two and the third night for half price!

8. "Fall" in love · Short drive to Blue Ridge Pkwy · Walk 2 resort & dining

9. Bear Tracks Cottage

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

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

12. Panoramic Peak: Wintergreen Condo with Views

13. Updated! Cozy and clean two bedroom condo.

14. Mountain View Vista: Resort Condo w/ Views

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

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

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

18. Mountain Retreat in Wintergreen!

19. 2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.

Find vacation rentals that suit your style

Top Wintergreen Hotel Reviews

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

Newly Built Designer Home in Wintergreen

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

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

Updated! Sleeps 14 - Hot Tub, Games, Fireplace, Pet Friendly, Firepits & Grill

Highlands Condo Views for days! Tons of details listed ⬇️☺️

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

Wintergreen Luxury, Best Views in VA!

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

Find out more about Wintergreen

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