Condo Rentals Wintergreen

A dense forest with a variety of coniferous trees and a small clearing with grass and a few scattered trees.

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Our top choices for Wintergreen condo rentals

A living room with a fireplace, a sofa with cushions, a coffee table, and a TV mounted above the fireplace.

1. Where the Trail Ends

Wintergreen Resort

Diana J.

includes taxes & fees

9 Sept - 10 Sept

A garden with a variety of flowers and trees at dusk.

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

Roseland

Michelle

includes taxes & fees

2 Sept - 3 Sept

A room with a wooden floor, a table with two stools, and a view through large windows with blinds.

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

Roseland

Deborah R.

includes taxes & fees

2 Sept - 3 Sept

A covered deck with wicker furniture, a black ottoman, and a sliding glass door leading to a forested area.

4. Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Resort

Scott M.

includes taxes & fees

3 Sept - 4 Sept

A wooden deck with a round table and chairs, overlooking a grassy area with trees.

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

Wintergreen Resort

Jennifer D.

includes taxes & fees

2 Sept - 3 Sept

A hotel room with a large bed, a desk, a chair, a lamp, and a view of the outdoor deck.

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

Wintergreen Resort

Alicia K.

includes taxes & fees

9 Sept - 10 Sept

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

Wintergreen Resort

Jennifer H.

includes taxes & fees

2 Sept - 3 Sept

A modern living room with a gray sectional sofa, a small coffee table, and a flat-screen TV mounted on the wall. Large windows provide a view of the cityscape.

8. Mountain View Vista

Nellysford

includes taxes & fees

2 Sept - 3 Sept

A scenic overlook with a metal railing, lush greenery, and distant mountains under a partly cloudy sky.

9. Panoramic Peak: Wintergreen Condo with Views

Wintergreen Resort

Art P.

includes taxes & fees

30 Sept - 1 Oct

A two-story house with a stone foundation, a large front porch, and a chimney.

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

Wintergreen Resort

Rob H.

includes taxes & fees

3 Sept - 4 Sept

A house with a covered porch, two Adirondack chairs, and a welcome mat.

11. Cozy Lux Condo at Wintergreen Resort

Roseland

Christopher H.

A living room with a fireplace, a sofa, a TV, and a dining area with a table and chairs.

12. Updated! Cozy and clean two bedroom condo.

Wintergreen Resort

Jason S.

includes taxes & fees

2 Sept - 3 Sept

A house with a covered patio, sliding glass doors, and a small outdoor seating area with chairs.

13. Mountain Retreat in Wintergreen!

Wintergreen Resort

Pam M.

includes taxes & fees

6 Sept - 7 Sept

A two-story log cabin with a balcony, a staircase, and a snow-covered roof.

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

Wintergreen Resort

Denise P.

A swimming pool surrounded by lush greenery and a wooden cabin.

15. 2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.

Wintergreen Resort

Shannon T.

includes taxes & fees

21 Sept - 22 Sept

A wooden deck with a sofa and a wicker chair, overlooking a lush green landscape with mountains.

16. Luxury Condo in the Sky! Finest in Wintergreen!

Wintergreen Resort

Charlie B.

A modern kitchen with white cabinetry, stainless steel appliances, a dining area with a wooden table and chairs, and a view through large windows.

17. Diamond Adventure at Wintergreen Resort FULLY UPDATED

Wintergreen Resort

Holly M.

A modern living room with a large sectional sofa, a fireplace, and a view of the mountains.

18. Firefly on The Ridge

Nellysford

includes taxes & fees

2 Sept - 3 Sept

A kitchen with wooden cabinets, a stainless steel refrigerator, a gas stove, and a granite countertop.

19. Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen Resort

Eric W.

20. Timbers Studio 46 with Wintergreen Advantage

Wintergreen

"We only stayed here for a night but it was both relaxing and quiet. The room was very clean and it was spacious for the two of us. It reminded me of a larger hotel room or a studio apartment. You could tell they had put some work into it to make it nice which I appreciated. You have to go to the front desk to check in but it’s not even a 2-minute drive from there. It took us a few minutes to locate it in the dark but that’s just because it’s so dark up there. Great place to stay on a couple...

Madison D.

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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!"

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."

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!"

Cozy Cabin with private HOT TUB!

10/10 Excellent

"The property was very clean and beautiful. It had some modern touches,yet felt rustic mountain. Plenty of room and comfortable. Beautiful views. Unfortunately it rained our three days,so we were unable to use the hot tub. But the rain on the surrounding trees sounded beautiful and the windows looking out gave a peaceful warm feeling. Gave us valuable family time. Hosts were great at communication."

Find out more about Wintergreen

Wintergreen Condo Rentals information

Number of reviews	797
Accommodation	328 Condo Rentals
Lowest Price	€154
Highest Price	€320

Frequently asked questions

How much do condos in Wintergreen cost?

You can expect to pay from €154 to €320 per night for condos in Wintergreen. No matter your budget, a terrific stay is a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your condo in Wintergreen with Expedia?

Booking a condo in Wintergreen is as simple as clicking on your travel dates and selecting a place suited to your needs. Chasing something low cost or luxurious, or a property that also comes with a pool and free WiFi? Use Expedia's search filters to narrow your results even further and find your dream fit.

How can I find cheap condos in Wintergreen?

Expedia can help you easily source cheap condos in Wintergreen. To lock in a terrific stay in a matter of clicks, try out our handy filter tool to refine your search results by budget, amenities and star rating.

What is there to do in Wintergreen near my condo?

The ideal travel accessory is a well-planned to-do list. Wintergreen Resort is a good spot to kick-start your sightseeing in Wintergreen.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wintergreen condo rentals

1. Where the Trail Ends

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

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

4. Wintergreen Condo -Steps to Ski and restaurants

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

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

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

8. Mountain View Vista

9. Panoramic Peak: Wintergreen Condo with Views

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

11. Cozy Lux Condo at Wintergreen Resort

12. Updated! Cozy and clean two bedroom condo.

13. Mountain Retreat in Wintergreen!

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

15. 2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.

16. Luxury Condo in the Sky! Finest in Wintergreen!

17. Diamond Adventure at Wintergreen Resort FULLY UPDATED

18. Firefly on The Ridge

19. Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

20. Timbers Studio 46 with Wintergreen Advantage

Find holiday rentals that suit your style

Top Wintergreen Hotel Reviews

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

Newly Built Designer Home in Wintergreen

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

Wintergreen cabin, hot tub, sauna, walk to trails

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

Wintergreen Luxury, Best Views in VA!

Luxury Condo in the Sky! Finest in Wintergreen!

New Build! Log Cabin with Hot Tub in Wintergreen

Cozy Cabin with private HOT TUB!

Find out more about Wintergreen

Wintergreen Condo Rentals information

Frequently asked questions

Search Wintergreen Condo Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Wintergreen condo rentals

1. Where the Trail Ends

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

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

4. Wintergreen Condo -Steps to Ski and restaurants

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

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

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

8. Mountain View Vista

9. Panoramic Peak: Wintergreen Condo with Views

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

11. Cozy Lux Condo at Wintergreen Resort

12. Updated! Cozy and clean two bedroom condo.

13. Mountain Retreat in Wintergreen!

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

15. 2BR 2BA + Bonus Kids Room. Walk to Slopes & Village. Dog-Friendly. Fireplace.

16. Luxury Condo in the Sky! Finest in Wintergreen!

17. Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

18. Firefly on The Ridge

19. Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

20. Timbers Studio 46 with Wintergreen Advantage

Find holiday rentals that suit your style

Top Wintergreen Hotel Reviews

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

Find out more about Wintergreen

Wintergreen Condo Rentals information

Frequently asked questions

17. Diamond Adventure at Wintergreen Resort FULLY UPDATED