6 Best Ski-In Ski-Out Accommodations In Wintergreen, Virginia - Updated 2024

Mich
Mich 
Updated
| 3 min read

Located in the counties of Augusta and Nelson, Wintergreen is a small town with a population of little over 500 (as per 2020 Census). The place is famous for the Wintergreen Resort, an all-year-round destination set on the eastern part of Blue Ridge Mountain. The many activities you can do here include skiing, golfing, mountain climbing, hiking, biking, and more. There is also plenty of amenities for you to discover. Apart from the resort, the area, just like any other, has plenty of restaurants, local shops, and nightspots. After an eventful day, this town also offers you numerous accommodation options, including nearby cabin rentals if you want a cozy space and pleasant Vrbo vacation rentals for a relaxing ambiance. And in case you’re just after skiing, you need to check out our list of the best ski-in ski-out accommodations in Wintergreen, Virginia.

We handpicked these listings carefully, considering (wherever possible) recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to ski slopes and equipment. The image galleries get refreshed with the latest updates regularly. They were last updated on February 07, 2024.

1. Quaint condo with spectacular mountain views (from USD 250)

If you’re planning to visit Wintergreen Resort, this cozy condo rental offers an indoor fireplace to keep you warm as the winter breeze approaches. If you want to prepare gastronomic delights, you can do it conveniently in its fully equipped kitchen. If you want to stay inside all day, you can tuck yourself into bed and stay entertained by watching your favorite Netflix show on its flat-screen TV.

After spending your day outside skiing, you can safely store your gear in its ski closet. You can also bring up to two fur babies here for a 100 USD pet fee. Make sure not to miss the scenic views provided by Raven’s Roost Overlook as well.

Stayed at this property?
Wintergreen Resort, Virginia, United States
2.49 km (1.6 mi) from Ravens Roost Overlook
condo 6 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
) the beds are extremely comfortable if you're the type who likes a firm mattress
the condo was comfortable and spacious
Cleanliness:
the colors were beautiful the condo was clean and the beds were comfortable
very nice cozy condo and surrounding area condo was clean and well laid out
the condo was clean comfortable and perfectly stocked with all we needed
Host:
owner was very responsive and very helpful
the owners are very responsive to emails through vrbo
owner said lines were supposed to be painted to help with this
Location:
the location was great at wintergreen to walk to the shops and lodge
the market and mountain inn (along with shops and restaurants) are all easy walking distance
Read more reviews
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2. Stylish rental with valley views (from USD 238)

Going on a trip around Wintergreen? This slopeside rental is perfect if you want to spend your time skiing during the winter holidays since it’s close to the Highlands Express ski lift. It has an airy balcony where you can adore the spectacular valley views this place offers. This charming condo unit also has a private pool for guests who want to relax. Other in-room amenities provided for your convenience include a washer, a dryer, a refrigerator, and a coffee maker.

To alleviate boredom, you can use the rental’s flat-screen TV, reading materials, and game console. If you’ll bring your car, you can also use the free parking space outside the property.

Stayed at this property?
Wintergreen, Virginia, United States
1.5 km (1.0 mi) from Ravens Roost Overlook
condo 8 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Amenities & Room:
the view was amazing and upstairs was nice and comfortable
condo was comfortable and had a ton of space we will definitely look to stay here again
comfortable stay and we would book again
Cleanliness:
very clean n easy to get to
everything was clean and comfortable and well laid out
the house was very clean which is very appreciated
the condo was clean and very well stocked with kitchen essentials
the space was very clean and well stocked with soaps toilet paper paper towels linens towels etc
Host:
owners were super easy to work with
Location:
the location was just perfect
so close to the slopes and such an inviting home
great location for skiers that can go down the black diamonds the lines are shorter
this was a wonderful experience the location is beautiful with great views from the whole property
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3. Loft-style condo unit for four (from USD 132)

Near many establishments, including shopping spots, restaurants, bars, and ski facilities, this Vrbo will surely make your ski holiday very convenient because ski spots are just a stone’s throw away. The master bedroom has a king-size bed and there’s also a queen-size sleeper sofa outside the room, therefore this property can sleep up to four people. It also has a large walk-in closet for your belongings. The open-floor-plan features a kitchen, dining for four, and a snug seating area. It also has a private balcony with a table and chairs, where you can have breakfast, read a book, or have your afternoon coffee while looking at the beautiful surrounding.

Stayed at this property?

2.34 km (1.5 mi) from Ravens Roost Overlook
105 reviews   Wifi Available
condo 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
very nice cozy apartment that actually looks and feels better in person than in the pictures
Cleanliness:
clean and well stocked
condo was clean and exactly as described
condo was extremely clean well decorated and set up efficiently
it was very clean and met all of our needs for our short get away
easy simple to find clean
Host:
the owner is very responsive to questions and very easy to work with
good communication with owner who was very helpful
Location:
this condo is in the perfect location
ideal location for hitting the slopes
location and size was perfect for my spouse and me
great location plenty of room very clean
location is great and the owner has thought of everything a guest may need while visiting
Read more reviews
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4. Two-bedroom apartment for a large group (from USD 289)

Want to enjoy your holidays in Wintergreen? Close to a ski resort in Virginia, this Vrbo holiday home is ideal for a large family or a group of friends. The location will let you ski-in and ski-out of the apartment. The two bedrooms with their cozy beds can comfortably accommodate up to eight guests. The open-plan space comes with a well-equipped kitchen, where you can cook a meal, a dining set-up, and a seating area. The bathroom comes with a shower and a bathtub. Other things to look forward to include an air conditioning unit, iHome music, HD flat-screen television, laundry facility, board games, and more.

Stayed at this property?
Wintergreen, Virginia, United States
7.18 km (4.5 mi) from Ravens Roost Overlook
condo 6 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Amenities & Room:
you could see the mountains from the living room and balcony it was precious
Location:
great location and would recommend to anyone
Read more reviews
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5. Self-contained condo in the heart of the Wintergreen Resort (from USD 209)

For travelers who want to explore the wonders of Wintergreen, this ski-in ski-out rental can welcome up to six guests. The Vrbo holiday home is a ski-in ski-out accommodation, where after putting on your skis, you can go straight to the slopes. Isn’t it convenient, especially if all you plan is to ski?

Apart from the bedrooms, the unit also comes with an open-plan, well-organized space that has a kitchen, dining for four, and a cozy living room set-up with a flat-screen television.

Stayed at this property?

2.34 km (1.5 mi) from Ravens Roost Overlook
17 reviews  
condo 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Host:
the place was very nice and the owner was very attentive and helpful
Location:
this was a fun comfortable and great location for us
this is a perfect place to stay
cable with hbo / cinemax -there were plenty of supplies and the place will sleep 5-6 comfortably
if you want to ski wintergreen this is a great place
Read more reviews
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6. Two-bedroom condo right behind the ski area (from USD 149)

Ski right at your back porch when you book this fully furnished condominium unit in Wintergreen. The accommodation has two bedrooms that can sleep up to four guests, ideal for two couples or a small family. The house is modern, has lovely furnishing, and comes with all the essentials, including a kitchen with a breakfast bar and a fridge. Also, it features a cozy seating area, where everyone can bond, play some board games, or just relax. Another great thing about this property is it’s near numerous dining options and ski facilities.

Stayed at this property?

2.16 km (1.4 mi) from Ravens Roost Overlook
40 reviews   Wifi Available
condo 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
my room was well furnished and the bed was comfortable
Cleanliness:
the condo is lovely and very clean
it was clean well appointed and the decor is tasteful and comfortable
complete updated and clean
this was our third year staying here and it was great as usual -- comfortable well appointed and clean
Host:
keith was very responsive and went the extra mile to make sure we had a good visit
glad to see the owners keep adding little touches and improvements every year
Location:
perfect location for a family with children
the location is ideal for walking to restaurants or accessing trails
nice clean place with great location on the slope within walking distance to everything needed
excellent condo in an excellent location
from the location next to the lodge and walking distant to the restaurants to the comfortable bed
Read more reviews
Earn OneKeyCash for every dollar spent on eligible hotels, vacation rentals, flights, car rentals, and more when you book across our family of brands.

Go skiing in Wintergeen

If the cold doesn’t bother you much, and skiing is one of your favorite sports or hobbies, then this place is the perfect destination for you. Wintergreen can offer you ski spots that are not only ideal for experts but also for beginners. But before going, make sure you’ve done your research, and to help you with that, here’s our list of the best ski-in ski-out accommodations in Wintergreen, Virginia.

Stayed at this property?

Frequently asked questions about ski-in ski-out accommodations in Wintergreen, Virginia

1. Which ski-in ski-out accommodations in Wintergreen have family-friendly amenities?

Planning for a family vacation in Wintergreen? If you’re looking for family-friendly ski-in ski-out accommodations in the area, check out this stylish rental with valley views as it offers a kid-friendly bunk bed and DVD games perfect for guests who’ll bring little companions during their stay.

2. Which ski-in ski-out accommodations in Wintergreen have parking?

Going on an adventure in Wintergreen? If you’ll bring your car during your stay, opt for accommodation options with a free parking space. With that, check out this stylish rental with valley views, this loft-style condo unit for four, and this two-bedroom condo right behind the ski area since they all have parking available.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Michelle, a devoted writer and travel enthusiast, endeavors to make a living through her love for words. Her objective is to explore the world, connect with diverse individuals, and motivate others...Read more

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