Wintergreen Vacation Rentals from CA $140: Short-Term Rentals for 2025

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Vacation Rentals in Wintergreen

"Easy to get to slopes. Comfortable house. Nice for a large family. "

"Everything was good. Could not get the tv in bedroom to work. Would like to have a Keurig type coffee maker"

CA $315 total

includes taxes & fees

Feb 24 - Feb 25

"What a great inviting space!We loved the setup and proximity to the slopes.We will be back for sure!!!"

"This was an amaizng VRBO. Heather was very responsive and accommodating. The codo itself is perfect for a family, or if you are a couple. As a family my kids, 8, 4 and 2 e joted the playroom nook with the Wii and the queen and twin beds. The views were spectacular. We arrived im the middle of Winter Storm Blair and got about a foot of snow dumped on us so the wood burning fireplace and board games were a hit as night creeped in. We are very thankful for heather and her VRBO and highly recommend....

"Right next to eagles swoop "

CA $603 total

includes taxes & fees

Feb 17 - Feb 18

"We had a great time. House was lovely and had everything we needed. The living area was spacious and accommodated large family gatherings for dinner and relaxing. The young adults liked the proximity to the slopes for snowboarding. We would definitely stay again. "

"Excellent stay overall. Weather kept us from enjoying the outside much but the cozy fireplace inside was super nice, especially with the supplied wood. Furniture was comfy and the smart TVs and streaming/cable was fabulous! "

"The condo was clean, cute and well stocked. The ski out location was just perfect for our ski trip to wintergreen "

"We had an awesome time! We were a little surprised by the size of the studio as it looked a bit bigger in the photos, but it was perfect for just my daugher and I. Smaller appliances due to being a smaller space for appliances (reminded me of our camper) but everything was in good working condition for the most part. The refrigerator froze our salad and veggies and the door of it would also get stuck on the counter so had to be careful that the door was always shut all the way. But as we were...

"Great place within walking to ski slope (Eagle swoop). Owner was great in communication and no issues at all with the place. nice decor!"

"The owners have thought of everything. From the comfy blankets to the cozy fireplace, we enjoyed skiing and relaxing over a weekend trip to Wintergreen. Taking in the sunrise while sipping coffee is a must! "

"- House is well taken care of. - House rule not wearing shoes inside and providing sleepers keeps the house clean. We liked it, but should mention that on VRBO listing. (It is listed on the competitors listing among the other info) Also, be better if the closed in shoes cabinet is available to protect the shoes from the weather. - Would be better if the property manager sent check-in info at least a day earlier than the middle of the day of check-in."

CA $1,493 total

includes taxes & fees

Feb 3 - Feb 4

"Love Mountain Lodge location. Great space for sleeping with the bunks and double bed. The furniture could use an update and squeaky floors - stairs and bathroom. "

"We had an amazing time staying at Wintergreen. Ashley was super easy to work with and the home was very accommodating! Everything was clean, spacious, with everything we needed. There was plenty of fire wood. We look forward to returning! "

"Fantastic views of the resort and the Blue Ridge mts. Easy to get in out of the condo with gear and only a 10 min walk or 2 min drive to Mountain Inn. I would recommend this property for any season you are planning a visit to Wintergreen. "

CA $354 total

includes taxes & fees

Feb 3 - Feb 4

Hanging Rock Cabin, 2 Bedrooms, Jetted Tub, Mountain View | Terrace/patio

"The cabin was very nicely set up, clean, and comfortable. The property manager was in constant contact with me to make sure I had everything I needed. I would highly recommend this place to anyone looking for a quiet relaxing escape. "

CA $384 total

includes taxes & fees

Feb 4 - Feb 5

"Wife and I were looking for a place away from the hustle that comes with NOVA normally, and especially the weekend of the inauguration. I must say we found the absolute best spot. Nelson county has always been a favorite spot for us to go to, but most of the time we have made day trips. I absolutely love being able to post up for a weekend in a quiet setting and being able to relax. Even the pup enjoys the quiet and are keen to relax next to the stoves. Most places just leave it up to you to...

"We have stayed here twice in the last two months. Both rooms were immaculately clean! Front office staff was pleasant and accommodating both times (It was the same woman both times...I just can't remember her name. ) If you are going to stay here, you so need to bring a hair dryer, conditioner (shampoo is provided), creamer( if you don't like French vanilla)"

CA $165 total

includes taxes & fees

Feb 9 - Feb 10

"Great quick stay in a lovely area with an amazing view"

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Other types of properties in Wintergreen you may be interested in

"Easy to get to slopes. Comfortable house. Nice for a large family. "

"This was an amaizng VRBO. Heather was very responsive and accommodating. The codo itself is perfect for a family, or if you are a couple. As a family my kids, 8, 4 and 2 e joted the playroom nook with the Wii and the queen and twin beds. The views were spectacular. We arrived im the middle of Winter Storm Blair and got about a foot of snow dumped on us so the wood burning fireplace and board games were a hit as night creeped in. We are very thankful for heather and her VRBO and highly recommend....

"The condo was clean, cute and well stocked. The ski out location was just perfect for our ski trip to wintergreen "

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, cottages, cabins, villas... 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 months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Wintergreen vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Wintergreen vacation rentals we have selected for you start as low as CA $140 per night. Entering your travel dates in the search wizard 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.

Wintergreen Vacation Rental Travel Info

Number of vacation rentals	3
Popular accommodation	Wintergreen condos
Known landmarks	Bold Rock Hard Cider Nellysford Cidery, Hill Top Berry Farm & Winery and Stoney Creek Golf Course
International airport	Charlottesville, VA (CHO-Charlottesville-Albemarle)

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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?

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.: Visitors give good reviews to this Wintergreen vacation home rental, which is located on a lake and has an outdoor pool, a fireplace, 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. It offers a balcony, a selection of games, and a spa tub so you can immerse yourself in your vacation. Some other top choices in Wintergreen are Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star! 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 43 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. Wintergreen Resort and Bold Rock Hard Cider Nellysford Cidery are a couple of places you'll find in the larger area.

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.

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Wintergreen Vacation Rentals

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Check prices for these dates

Vacation Rentals in Wintergreen

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

The Modern Mountain Condo

Modern Luxe Treetop Retreat w/ Hot Tub, Gas Fire Pit, Steps to Ski! 100% 5 Star!

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

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

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

Fantastic Mountain & Valley Views! Top of the Mountain & Close to the Resort!

Ski-In/Ski-Out Comfy Condo

Ski In & Out Mountain & Firework Views Studio

Newly Updated Cozy Condo in the Heart of Wintergreen! Pet friendly.

Best views on Mountain! Breathtaking 5 Star. Available Midweek Ski! BOOK NOW!

Spacious 6-bedroom cabin in charming Wintergreen Resort

Luxury Slope Side Home in Wintergreen Resort! Sauna, Smart Tv's, Central!

Snug Wintergreen Resort Studio: Ski In & Out!

Blue Ridge Mountain Retreat in Wintergreen

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

Love Ridge Mountain Lodging

Unwind in Seclusion: Log Cabin retreat with Wood Burning Stove & Game Table

Valley Extended Suites

View from the Top

Other types of properties in Wintergreen you may be interested in

Hot Tub! FAST WiFi, Firepit! Hiking off Property! 70"&60” HDTVs Cozy 4BR House.

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

Ski-In/Ski-Out Comfy Condo

Find out more about Wintergreen

Wintergreen Vacation Rental Travel Info

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