
Apartment vacation rentals in Wintergreen Resort
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Top-rated apartment rentals in Wintergreen Resort
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Popular amenities for Wintergreen Resort apartment rentals
Weekly apartment rentals

Wintergreen Resort Retreat Private Pool for Guests
We stayed in this condo for a fun ski weekend and were so happy with everything. Great location! We shuttled our ski stuff up to the drop off area for ease with the kids (one of us dropped off the fam and gear and parked the car and walked up in our ski boots- took about 5 min) and we all walked home with our gear at the end of the day. Really convenient being so close to the market for any treats or snacks we wanted. The condo itself was plenty spacious for the 4 of us and had everything we needed. We had a great weekend, thank you!!

Cozy Basement Apartment with Private Entrance
We really enjoyed our stay! The apartment was very clean and comfortable. The kitchen was an added bonus. Emily was very responsive and helpful. Would definitely recommend staying here if you’re in the area.

Walker's dream. Close to downtown.
Really nice stay close to downtown. We felt comfortable and safe. Provided exactly what we needed. Would recommend and stay again.

Spacious lower level Airbnb! READ SUMMARY!
Loved this spot! Needed a place to stay for a few big gravel rides... this place was perfect!

Slope-Side with a Mountain View
We had a fabulous time at Sandy’s place! It was a beautiful home inside and the views of the sunrise were AMAZING! 🌄🌄It was great to sit on the deck each morning! It’s a fabulous location with a hiking trail steps from the house, not to mention a sandwhich market and pizza place within walking distance! We didn’t need to bring any food, just went to the market which had everything! After a fall hike it’s a great place to relax and watch some football in the trees! It’s a beautiful home full with all the things you need, comfy beds and blankets a beautiful kitchen and plenty of space - I can’t wait to go back!

Newly renovated 2BR downtown apartment
We enjoyed our stay while visiting family in the area. The unit was just as described, well furnished and cozy. The bed was firm and comfortable - a real plus. Little things like fluffy towels made daily routines more comfortable. The location is right in downtown Staunton in a very walkable area. We drove into town and never had an issue with finding free parking on the street - usually right out front. We did have a concern with the bakery below the unit playing loud music early in the morning (on days the bakery wasn't open), but Simon and Kirk were very responsive and quick to address the issue for us, which we really appreciated.

Ready for Ski Season! Book NOW!
It was very clean with all working amenities. Great location from the slopes. All around great place to stay.

Bright Crozet Apartment w/ Mountain Views!
Lovely setting. Clean and comfortable. Enjoyed our stay. Recommend.
Private apartment rentals

Lovingston Get-Away Lovingston, VA
Great cozy spot in Lovingston! Ed was a wonderful host, very responsive and helpful. Despite all the rain we were able to have a lovely weekend getaway. Wineries and restaurant options close by.

Spacious Apartment. Short walk to downtown
It is spacious apartment for my wife and me to stay in for the weekend with lots of nice amenities. Easy walk to the downtown area, massive bed, great selection of simple entertainment (books and TV streaming apps). The Berkey water filter was a nice touch too.

The Hideaway Suite: Sauna & Lux Amenities
I booked this place for my parents and they loved it!

* King Bedroom * Apartment in Victorian Mansion *
Great stay in beautiful Virginia. Staunton’s hills are great to get a good view of the Blue Ridge Mountains. If you walk up to the top of N Jefferson, you can get a pretty sweet view of the mountains in the winter. The stay at this Air B and B was great. It had everything you would need and a very cozy vibe. The decor in the Air B and B will bring you back to a more retro time period. Everything is thoughtfully placed with a focus on simplicity which I appreciated. Lots of great restaurants right down the road on West Beverly. Such a cool place to stay, unlike any other!

The Storefront: Downtown Staunton + Unique Stay
Unique property in the perfect location! Walk to food and shops. Super comfy with everything you need. Love the bar on the first floor!

Piedmont Place 401| Lux Vineyard & Brewery Getaway
We had a wonderful time. It was a great place to stay close to wineries and breweries.

Big Blue #2: Spacious&Modern.
This is exactly what AirBnb is supposed to be - a place that feels like home. All the necessary tools for cooking meals. All the linens and towels you need. Laundry detergent and brand new washer and dryer. Peaceful. Spacious. Close to multiple really good restaurants. This is a 10/10 recommend!

Mtn Vineyards Getaway
The location was beautiful, the apartment was cute and clean, and the host was extremely communicative and helpful. Regardless of what brings you to the Crozet area, I would definitely recommend staying here!
Family-friendly apartment rentals

The Attic in Restored Mansion Walk everywhere!
Perfect location just steps from magical downtown Staunton and the Blackfriars Thester in a very livable, restored and private historic home with a private rooftop deck, full kitchen, lovely views, private entrance, easy parking, charming ambience, and every convenience! One of the favorite Airbnbs we’ve stayed at, with a fabulous hostess who had helpful recs to meet every need. We will be back!

The Barn at Haden near Wineries and C'ville
Loved our stay in Crozet! The Red Barn was perfect for a visit in Charlottesville for 4 adults and 1 baby. We appreciated all the amenities they had (including lots of basics for a baby) and the ability to walk into town for coffees and dinner. Thanks for a great visit!

Studio Apt. in Wine/Brewery Country/on 151
This is my second stay at Sarah’s and I hope not my last. My dog loves the place and grounds too!

Walk to Market/Slopes!
As advertised. Good location. Easy check-in

Minutes to BC Brewery BR Parkway 151 Wintergreen
This place was perfect for our short term stay! It had everything we needed. Would definitely stay here again.

Close to Activities/Shops/slopeside
Jeffery's condo was perfect for our family's short trip to Wintergreen. The interior setup was comfortable and the location was right off the slopes with great views. The weather was excellent and we wished we had the time to stay longer. We will definitely try to book another stay here next year. Thank you for allowing us to use your wonderful place for our trip!

Spacious 2 bedroom, 2 bath condo w/ full kitchen
Great stay. Not updated, but extremely comfortable. Bed was great! We really enjoyed the fireplace. Everything we needed for a short stay. Small suggestion… get rid of the cable and tv and buy a smart tv for streaming. Thanks for a great stay and for allowing us a later checkout. Much appreciated.

Earth Room Suite at Galleywinter Farm
It was really great for our family to get away for a few days over Thanksgiving! The property is beautiful and peaceful, and the suite was cozy. Overall we enjoyed the flexibility of having a few different rooms, being able to cook (as much as we needed/wanted to), and the fact that the earth room doesn't have windows allowed us to sleep in late. As far as amenities, the tub pretty amazing. I also really enjoyed peeking at some of the crafting books on the bookshelves - the cowgirl room in particular has a workshop feel that I enjoyed! Really grateful we were able to go on this trip - thank you!
Quick stats about apartment rentals in Wintergreen Resort
Total rentals
20 properties
Nightly prices starting at
ﺩ.ﺇ257 before taxes and fees
Total number of reviews
1.6K reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
10 properties have a pool
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- Massanutten Resort
- Omni Homestead Resort
- Ash Lawn-Highland
- Chisholm Vineyards at Adventure Farm
- Homestead Ski Slopes
- Spring Creek Golf Club
- Early Mountain Winery
- Amazement Square
- Massanutten Ski Resort
- Frontier Culture Museum
- Wintergreen Resort
- Liberty Mountain Snowflex Centre
- Boonsboro Country Club
- The Plunge Snow Tubing Park