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10 Oct - 12 Oct
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17 Oct - 19 Oct
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31 Oct - 2 Nov
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Featured Condo Rentals in Wintergreen and around

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Miscellaneous

Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!

10.0 out of 10, Exceptional, (244)
"Tremendous view and perfect accommodations. We used for a base to visit Staunton and Charlottesville. "
Best views on Mountain! Breathtaking 5 Star condo!. Booking NOW for 2026!
Wintergreen. Sunset Vista Villa - Sea of Mountains
Interior

Wintergreen. Sunset Vista Villa - Sea of Mountains

10.0 out of 10, Exceptional, (81)
"Rebeca is a fantastic host! She's very responsive and accommodating. We enjoyed our stay very much much and would love to come back. "
Wintergreen. Sunset Vista Villa - Sea of Mountains
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
A heated pool

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

9.8 out of 10, Exceptional, (134)
"Great ski-in / ski-out."
Eagles Court Ski In/Ski Out Condo with Walkable Location & Mountain Views!
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Fridge, microwave, oven, stovetop

Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes

9.6 out of 10, Exceptional, (49)
"We had the best weekend! Loved Lake Monocan and Devil’s Knob Spa. Also visited Three Notched and Devil’s Backbone. Condo worked very well. Beds were so comfortable and we lived kicking back on the patio. Will definitely rent again since it’s so close. Thanks for great communications!"
Rosie's Retreat: Cozy 3 BR, 3 Bath Condo in Wintergreen Resort, 1 mile to slopes
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes

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

10.0 out of 10, Exceptional, (327)
"The property is nestled very nicely on the mountain and convenient to the main lodge, restaurants and other attractions. We really enjoyed our stay. The condo was plenty big for the two of us and our dog. It is well-appointed Kudos to the owner, Heather, for thinking of everything to make our stay great. "
Wintergreen Pet-Friendly Condo: Walk to Mountain Inn & Slopes
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
Outdoor dining

Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort

8.0 out of 10, Very good, (1)
Breathtaking mountain views in a 2-bedroom condo at Wintergreen Resort
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

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

9.0 out of 10, Wonderful, (293)
"Beautiful location and million dollar views are so true. The condo was clean and comfortable. Will stay again and recommend to everybody. "
The price is €212
includes taxes & fees
1 Oct - 2 Oct
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Endless Mountain Top Views from All The Way Up!
Property grounds

Endless Mountain Top Views from All The Way Up!

10.0 out of 10, Exceptional, (85)
"Great place to stay. We stayed here on our way to the Outer Banks. Very very clean and comfortable.Thanks!"
Endless Mountain Top Views from All The Way Up!
Updated! Cozy and clean two bedroom condo.
Terrace/patio

Updated! Cozy and clean two bedroom condo.

9.4 out of 10, Exceptional, (25)
"Great location and was very clean and cozy! We will definitely book this condo again!"
Updated! Cozy and clean two bedroom condo.
Panoramic Peak: Wintergreen Condo with Views
TV, fireplace

Panoramic Peak: Wintergreen Condo with Views

9.6 out of 10, Exceptional, (30)
"With its breathtaking views, this property is a hidden gem. It is also very well maintained. "
The price is €256
includes taxes & fees
1 Oct - 2 Oct
Panoramic Peak: Wintergreen Condo with Views
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
Smart TV, fireplace, DVD player

Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC

9.8 out of 10, Exceptional, (53)
"This was our second stay in Wintergreen. First time at this property. The condo was beautifully decorated, had all the necessities and the view was breathtaking. "
Cozy 2-bedroom condo with stunning views of lovely Wintergreen WiFi, AC
Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking
Smart TV, fireplace

Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking

10.0 out of 10, Exceptional, (4)
"Exterior of the building is a bit dated, but this unit has a fresh and updated feel to it. Everything we needed was provided. Quiet and very clean. Host was easy to work with. I'll definitely check to see if this unit is available the next time I'm visiting.Note: As mentioned in the description, there are a lot of steps to go down (and then back up)."
Wintergreen Mountain Views - Diamond in the Slopes - Close to Breweries & Hiking
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
Property grounds

Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️

10.0 out of 10, Exceptional, (175)
"Great Wintergreen condo."
Dobie condo, renovated top to bottom! LOTS OF DETAILED INFO LISTED ☺️
Charming 2-bedroom condo in beautiful Wintergreen Resort
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom condo in beautiful Wintergreen Resort

10.0 out of 10, Exceptional, (1)
"We stayed here for a couple of nights over July 4th and it was a nice short getaway. The condo is in a good location - 5 min walk to resort restaurants - and is very comfortable. The kitchen is well-equipped with plenty of cooking tools. The living room seating space was comfortable and allowed for just hanging out. We really enjoyed our stay! "
The price is €335
includes taxes & fees
1 Oct - 2 Oct
Charming 2-bedroom condo in beautiful Wintergreen Resort
Majestic Mountain View’s from The Cliffs
Interior

Majestic Mountain View’s from The Cliffs

9.6 out of 10, Exceptional, (34)
"Quiet, cute condo close to the slopes with great views. We enjoyed a long weekend as a family and had all the things we needed to enjoy our stay!"
Majestic Mountain View’s from The Cliffs
Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!
Dining

Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!

10.0 out of 10, Exceptional, (149)
"Probably the best VRBO we have ever stayed in! Perfectly clean and well appointed! Definitely recommend to everyone!"
Highlands Condo LOTS OF DETAILED INFO LISTED☺️ Views for days!
Time to Book for Spring and Summer...Amazing Views and 5-Star Amenities
Outdoor dining

Time to Book for Spring and Summer...Amazing Views and 5-Star Amenities

10.0 out of 10, Exceptional, (302)
"Amazing stay with everything g we needed. It would be nice to have access to a pool. "
Time to Book for Spring and Summer...Amazing Views and 5-Star Amenities
Recently updated - breathtaking view of the Blue Ridge Mountains
Property grounds

Recently updated - breathtaking view of the Blue Ridge Mountains

9.8 out of 10, Exceptional, (39)
"Everything was just as represented in the write up and the Host was great."
Recently updated - breathtaking view of the Blue Ridge Mountains
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Interior

WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS

10.0 out of 10, Exceptional, (75)
"Lots to do in the area, and everything you need in the home."
WINTERGREEN RESORT HOME WITH BLUE RIDGE VIEWS
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Interior

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

9.8 out of 10, Exceptional, (17)
"Excellent throughout"
The price is €219
includes taxes & fees
2 Oct - 3 Oct
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
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.
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Top Wintergreen Hotel Reviews

Holiday Inn Express & Suites Waynesboro East by IHG

Holiday Inn Express & Suites Waynesboro East by IHG

10/10 Excellent
"The hotel staff was friendly. The place is very clean. Breakfast was great! "
Rachel 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites Waynesboro East by IHG

Find out more about Wintergreen

Find out more about Wintergreen

Wintergreen Condo Rentals information

Number of reviews
1,974
Accommodation
306 Condo Rentals
Lowest Price
€212
Highest Price
€335

Frequently asked questions

How much do condos in Wintergreen cost?
You can expect to pay from €212 to €335 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?
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