Wintergreen Vacation Rentals

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Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Wintergreen vacation rentals

Terrace/patio

Wintergreen Condo -Steps to Ski and restaurants

Wintergreen Condo -Steps to Ski and restaurants
Wintergreen Resort
9.8 out of 10, Exceptional, (32 reviews)
"Check in was a breeze, amazing location and great nights stay."
United States
Garrett P.
$236 nightly
The price is $265
Apr 7 - Apr 8
Total with taxes and fees
Wintergreen Condo -Steps to Ski and restaurants
Property grounds

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, (149 reviews)
"Very clean and pet-friendly "
United States
Heston
$215 nightly
The price is $241
Apr 7 - Apr 8
Total with taxes and fees
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
Exterior

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

Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Wintergreen Resort
10.0 out of 10, Exceptional, (105 reviews)
"Great stay with a fabulous view! Very cozy and comfortable! We had a wonderful little getaway!"
United States
Vicki E.
$254 nightly
The price is $285
Apr 7 - Apr 8
Total with taxes and fees
Wintergreen. Panoramic Sunsets, Mountain Views, Private Deck + Fireplace
Exterior

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.
$278 nightly
The price is $294
Apr 7 - Apr 8
Total with taxes and fees
Laurelwood Hollow: Walk to Ski & Swim
TV, fireplace

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 view!"
United States
Serge L.
$259 nightly
The price is $291
Apr 7 - Apr 8
Total with taxes and fees
Mountain View Vista: Resort Condo w/ Views
Fridge, microwave, oven, stovetop

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

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Wintergreen Resort
10.0 out of 10, Exceptional, (34 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 7 - Apr 8
Total with taxes and fees
Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Fridge, microwave, oven, stovetop

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.
$288 nightly
The price is $323
Apr 7 - Apr 8
Total with taxes and fees
Wintergreen Ski Retreat, Cozy Condo Near Slopes & Devils Knob Golf
Interior

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 7 - Apr 8
Total with taxes and fees
Cozy 1 Bedroom Condo Off 12th Hole at Devil's Knob Golf Course
Fridge, microwave, oven, stovetop

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 Condo and owner. Great access to slopes, well appointed and clean. Beautiful views and can walk to everything in the heart of the resort "
United States
Patrick E.
$356 nightly
The price is $394
Apr 7 - Apr 8
Total with taxes and fees
Diamond Adventure at Wintergreen Resort *FULLY UPDATED*
Smart TV

Serenity Cabin-Woodland Retreat

Serenity Cabin-Woodland Retreat
Wintergreen Resort
10.0 out of 10, Exceptional, (11 reviews)
"Great house and great host!"
United States
Joe B.
$350 nightly
The price is $393
Apr 7 - Apr 8
Total with taxes and fees
Serenity Cabin-Woodland Retreat
Fireplace

The Modern Mountain Condo

The Modern Mountain Condo
Wintergreen Resort
10.0 out of 10, Exceptional, (47 reviews)
"The property was just as described and the communication was a breeze. The view from the unit’s deck was beautiful. "
United States
Susan
$204 nightly
The price is $229
Apr 7 - Apr 8
Total with taxes and fees
The Modern Mountain Condo
TV, fireplace

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.
$316 nightly
The price is $320
Apr 7 - Apr 8
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)
"I love this place!!! Will book again everytime we are there!"
United States
Thavikiet T.
$227 nightly
The price is $254
Apr 9 - Apr 10
Total with taxes and fees
2br/2ba: Million Dollar View from Luxury Condo on the Ridge.
Outdoor dining

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.
$230 nightly
The price is $258
Apr 7 - Apr 8
Total with taxes and fees
Escape to the Blue Ridge Mountains at Wine-tergreen!
1 bedroom, desk, internet, bed sheets

Panoramic Peak: Wintergreen Condo with Views

Panoramic Peak: Wintergreen Condo with Views
Wintergreen Resort
9.8 out of 10, Exceptional, (41 reviews)
"The location was great and the sunrise views were amazing!"
United States
Jennifer B.
$258 nightly
The price is $290
Apr 12 - Apr 13
Total with taxes and fees
Panoramic Peak: Wintergreen Condo with Views
Exterior

Diamond Hill Studio 09 with Wintergreen Advantage

Diamond Hill Studio 09 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (2 reviews)
"Great location and cozy condo! "
United States
Molly M.
$238 nightly
The price is $267
Apr 7 - Apr 8
Total with taxes and fees
Diamond Hill Studio 09 with Wintergreen Advantage
Smart TV, fireplace, books

Spacious + Serene Mtn Top Escape, 4 En Suites

Spacious + Serene Mtn Top Escape, 4 En Suites
Wintergreen Resort
10.0 out of 10, Exceptional, (53 reviews)
"The place was very clean and spacious. The communication from the hosts was helpful. We had a very pleasant stay."
United States
James S.
$302 nightly
The price is $339
Apr 7 - Apr 8
Total with taxes and fees
Spacious + Serene Mtn Top Escape, 4 En Suites
Exterior

Mountain Inn Lodge 54 with Wintergreen Advantage

Mountain Inn Lodge 54 with Wintergreen Advantage
Wintergreen
10.0 out of 10, Exceptional, (3 reviews)
"We were in the area looking to possibly relocate and this loft on the mountain was a beautiful stay. Convenient to restaurants within walking distance. We would definitely book again!"
United States
Erin C.
$219 nightly
The price is $246
Apr 7 - Apr 8
Total with taxes and fees
Mountain Inn Lodge 54 with Wintergreen Advantage
Property grounds

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, (13 reviews)
"Fantastic little studio located right at the slopes. Very clean and many thoughtful touches. Great stay. "
United States
Lloyd F.
$196 nightly
The price is $220
Apr 12 - Apr 13
Total with taxes and fees
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
Exterior

Three Ridges 64 With Wintergreen Advantage

Three Ridges 64 With Wintergreen Advantage
Chestnut Springs
$267 nightly
The price is $300
Apr 7 - Apr 8
Total with taxes and fees
Three Ridges 64 With Wintergreen Advantage
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

The Modern Mountain Condo

The Modern Mountain Condo

10/10 Excellent
"This was an amazing cozy place for the weekend. Everything is near by and easy to get to. The kit hen is well stocked for cooking, and the back porch was lovely to sit on. "
Daniel T. 2-night trip
Posted 5 days ago
The Modern Mountain Condo

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 $229 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.

Explore a world of travel with Expedia

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 Insane Mountain Views - New Listing.

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.