Wintergreen Vacation Rentals

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Our top choices for Wintergreen vacation rentals

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (33 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
$238 nightly
The price is $267
Apr 19 - Apr 20
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.8 out of 10, Exceptional, (42 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
$261 nightly
The price is $293
Apr 19 - Apr 20
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views

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

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Roseland
9.6 out of 10, Exceptional, (151 reviews)
"Very clean and pet-friendly "
United States
Heston
$222 nightly
The price is $249
Apr 19 - Apr 20
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly

Endless Mountain Top Views from All The Way Up!

Endless Mountain Top Views from All The Way Up!
Wintergreen Resort
10.0 out of 10, Exceptional, (101 reviews)
"The mountain views from the balcony are spectacular!"
United States
Becca R.
$215 nightly
The price is $241
Apr 19 - Apr 20
Total with taxes and fees
Endless Mountain Top Views from All The Way Up!

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (35 reviews)
"Cozy, clean very attentive host Paul was amazingThis cozy kid friendly family home was very accommodating. Def will be back again!!"
United States
Pamela P.
$275 nightly
The price is $308
Apr 18 - Apr 19
Total with taxes and fees
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining

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

Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!
Wintergreen Resort
10.0 out of 10, Exceptional, (31 reviews)
"Well stocked house with great layout for families or two couples. Great kitchen setup with everything you’ll need. Close to the resort and skiing. Close to hiking trails. "
United States
Jeremiah H.
$289 nightly
The price is $325
Apr 20 - Apr 21
Total with taxes and fees
Cozy chalet w/ king beds, fireplace, and hot tub. Close to hiking! Dog-friendly!

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

Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Wintergreen Resort
9.4 out of 10, Exceptional, (14 reviews)
"We enjoyed our stay here. Brought the whole family."
United States
Caroline D.
$286 nightly
The price is $321
Apr 20 - Apr 21
Total with taxes and fees
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (107 reviews)
"Very nice, updated place with everything we needed. We would definitely stay here again!"
United States
Kimberly M.
$290 nightly
The price is $325
Apr 27 - Apr 28
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace

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

Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Roseland
9.8 out of 10, Exceptional, (30 reviews)
"Wonderful cozy condo close to the golf course and the slopes. "
United States
Deborah R.
$216 nightly
The price is $243
Apr 20 - Apr 21
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course

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

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Wintergreen Resort
10.0 out of 10, Exceptional, (14 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
$191 nightly
The price is $214
Apr 20 - Apr 21
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge

Wintergreen Resort Condo Available Now!!

Wintergreen Resort Condo Available Now!!
Wintergreen Resort
9.8 out of 10, Exceptional, (25 reviews)
"Super clean and equipped with everything you need (just bring your own hangars). Very comfortable bed. "
United States
Pam M.
$319 nightly
The price is $324
Apr 19 - Apr 20
Total with taxes and fees
Wintergreen Resort Condo Available Now!!

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

2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Roseland
9.0 out of 10, Wonderful, (317 reviews)
"We enjoyed our time at the stay. "
United States
michael b.
$222 nightly
The price is $249
Apr 22 - Apr 23
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.

Escape to the Blue Ridge Mountains at Wine-tergreen!

Escape to the Blue Ridge Mountains at Wine-tergreen!
Wintergreen Resort
9.8 out of 10, Exceptional, (126 reviews)
"Everything was as is listed, we were off season so hiking and scenic views is what there was to do, relaxing. Host was accessible on phone, place was clean. "
United States
David L.
$229 nightly
The price is $257
Apr 19 - Apr 20
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (48 reviews)
"Great place to stay to hit the ski slopes. Just a short walk to the slopes and right next to the gas station/ small grocery shop to easily pick up some food on the way back from skiing. "
United States
Joyce B.
$210 nightly
The price is $236
Apr 19 - Apr 20
Total with taxes and fees
The Modern Mountain Condo

Mountain Inn Studio 94 with Wintergreen Advantage

Mountain Inn Studio 94 with Wintergreen Advantage
Wintergreen
$203 nightly
The price is $228
Apr 19 - Apr 20
Total with taxes and fees
Mountain Inn Studio 94 with Wintergreen Advantage

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Wintergreen Resort
10.0 out of 10, Exceptional, (38 reviews)
"Amazing spot! Ski in - out was so convenient and a quick walk to the village! Phyllis was amazing and the condo was beautiful! Would definitely book this condo again! "
United States
Susan J.
$370 nightly
The price is $409
Apr 19 - Apr 20
Total with taxes and fees
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*

Three Ridges 64 With Wintergreen Advantage

Three Ridges 64 With Wintergreen Advantage
Chestnut Springs
$266 nightly
The price is $299
Apr 18 - Apr 19
Total with taxes and fees
Three Ridges 64 With Wintergreen Advantage

Laurelwood Hollow: Walk to Ski & Swim

Laurelwood Hollow: Walk to Ski & Swim
Wintergreen Resort
10.0 out of 10, Exceptional, (8 reviews)
"We really enjoyed our stay here! Great location, and the condo was very clean and well stocked. Communication with the host was excellent as well. We look forward to returning back some day!"
United States
Alexander H.
$265 nightly
The price is $279
May 11 - May 12
Total with taxes and fees
Laurelwood Hollow: Walk to Ski & Swim

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (12 reviews)
"Great house and great host!"
United States
Joe B.
$335 nightly
The price is $377
Apr 20 - Apr 21
Total with taxes and fees
Serenity Cabin-Woodland Retreat

Mountain View Vista: Resort Condo w/ Views

Mountain View Vista: Resort Condo w/ Views
Wintergreen Resort
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful condo"
United States
Mary C.
$261 nightly
The price is $293
Apr 19 - Apr 20
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views
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

Find out more about Wintergreen

Everything you need to know about Wintergreen vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Wintergreen vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Wintergreen vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Wintergreen vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Wintergreen. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Wintergreen in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $236 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Wintergreen rentals

At Expedia, we put the best Wintergreen vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Wintergreen rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Wintergreen vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Wintergreen. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Incredible Mountain Views - Modern Four Bedroom Home - Five Minute Walk to Slope: Visitors give good reviews to this Wintergreen vacation home rental, which is located in the mountains and has a patio, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Wintergreen are Upscale and Family-Friendly in Wintergreen and Newly Rebuilt Home - Hot Tub - Sauna - Sleeps 14.

How many vacation rentals are there in Wintergreen?

Choose from 223 Expedia vacation rentals in Wintergreen for a memorable vacation.

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 Stoney Creek Golf Course 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.