Apartment vacation rentals in Wintergreen Resort

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Popular amenities for Wintergreen Resort apartment rentals

Weekly apartment rentals

A cozy condo is partially visible behind snow-covered trees, with a deck and wooden railing leading to snow-blanketed steps. The scene is enhanced by gentle snowfall, creating a serene winter landscape.
Apartment in Roseland
4.85 out of 5 average rating, 176 reviews

Wintergreen Resort Retreat Private Pool for Guests

CaseyRating, 5 stars27 months ago
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!!
Guest favorite
A cozy living room features a comfortable sofa with decorative pillows and a rustic wooden coffee table. A reclining chair is visible, and a framed wall art piece adds character. The space is well-lit with natural light from nearby windows, providing a welcoming atmosphere.
Apartment in Stuarts Draft
4.96 out of 5 average rating, 52 reviews

Cozy Basement Apartment with Private Entrance

MelissaRating, 5 stars13 months ago
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.
Guest favorite
The exterior of the building displays a two-story structure with light brown siding and a front porch adorned with white railings. Windows are visible on both levels, complemented by a small garden and walkway leading up to the entrance.
Apartment in Staunton
4.92 out of 5 average rating, 101 reviews

Walker's dream. Close to downtown.

ErinRating, 5 stars5 days ago
Really nice stay close to downtown. We felt comfortable and safe. Provided exactly what we needed. Would recommend and stay again.
The exterior features a two-story home with a welcoming red front door. The entrance is accessible by a wooden staircase, surrounded by a deck and landscaped with trees and fallen leaves. A paved driveway accommodates parking for multiple vehicles.
Apartment in Waynesboro
4.75 out of 5 average rating, 504 reviews

Spacious lower level Airbnb! READ SUMMARY!

JakeRating, 5 stars2 days ago
Loved this spot! Needed a place to stay for a few big gravel rides... this place was perfect!
A cozy living area is present, featuring a spacious sectional sofa adorned with colorful throw pillows. A coffee table is positioned centrally, and a large flat-screen television is mounted on the wall. Natural light streams through expansive windows, highlighting the warm wood accents.
Apartment in Wintergreen Resort
4.67 out of 5 average rating, 3 reviews

Slope-Side with a Mountain View

AmandaRating, 5 stars6 months ago
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!
Top guest favorite
A modern living area is furnished with a sectional sofa and accent chairs, arranged around a circular rug. A flat-screen TV is mounted on the wall, complemented by framed artwork. Ambient lighting is provided by a multi-bulb floor lamp and a ceiling fan adds comfort.
Apartment in Staunton
4.94 out of 5 average rating, 143 reviews

Newly renovated 2BR downtown apartment

DesiraeRating, 5 stars2 weeks ago
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.
Guest favorite
A cozy living area features a light-colored sectional sofa positioned around a wooden coffee table. A fireplace is set against a wood-paneled wall. A TV is mounted above the mantel, and the space is complemented by warm lighting and a view through large windows.
Apartment in Wintergreen Resort
4.96 out of 5 average rating, 23 reviews

Ready for Ski Season! Book NOW!

HudsonRating, 5 stars3 months ago
It was very clean with all working amenities. Great location from the slopes. All around great place to stay.
Guest favorite
A bright living area features a light-colored couch with textured pillows and a wooden coffee table. The open kitchen, equipped with modern appliances, is visible in the background. Natural light streams through multiple windows, enhancing the inviting atmosphere.
Apartment in Crozet
4.95 out of 5 average rating, 44 reviews

Bright Crozet Apartment w/ Mountain Views!

MaryRating, 5 stars4 weeks ago
Lovely setting. Clean and comfortable. Enjoyed our stay. Recommend.

Private apartment rentals

Guest favorite
A wooden deck is elevated and features a vibrant red umbrella. Surrounding the deck are leafy green plants and a small seating area with pink chairs. A lattice design is present under the deck, adding texture to the space.
Apartment in Lovingston
4.89 out of 5 average rating, 136 reviews

Lovingston Get-Away Lovingston, VA

JacquelynRating, 5 stars2 months ago
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.
Guest favorite
A spacious living area features a large leather sofa and an accent chair beside a floor lamp. Natural light filters through two windows, enhancing the neutral color palette. A patterned area rug covers the hardwood floor, complemented by a wall mirror and a simple chandelier.
Apartment in Staunton
4.93 out of 5 average rating, 14 reviews

Spacious Apartment. Short walk to downtown

CalvinRating, 5 stars3 weeks ago
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.
Guest favorite
A cozy living area features exposed brick walls complemented by wood beam ceilings. Natural light fills the space through two large windows adorned with woven shades. Plush sofas are decorated with an array of colorful cushions, while a small potted plant adds a touch of greenery.
Apartment in Staunton
4.96 out of 5 average rating, 142 reviews

The Hideaway Suite: Sauna & Lux Amenities

JosephRating, 5 stars1 month ago
I booked this place for my parents and they loved it!
Top guest favorite
A cozy living area features a navy blue sofa paired with a white coffee table. A red accent chair stands beside a television on a yellow media console. Natural light enters through a window, and air conditioning is discreetly mounted on the wall.
Apartment in Staunton
5 out of 5 average rating, 13 reviews

* King Bedroom * Apartment in Victorian Mansion *

RachelRating, 5 stars3 months ago
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!
Guest favorite
A welcoming living area features a gray sofa adorned with a soft throw and decorative pillows. A cozy electric fireplace stands nearby, while a textured area rug complements the space. Large windows allow natural light to illuminate the room, showcasing a view of the street outside.
Apartment in Staunton
4.96 out of 5 average rating, 228 reviews

The Storefront: Downtown Staunton + Unique Stay

SusanRating, 5 stars2 months ago
Unique property in the perfect location! Walk to food and shops. Super comfy with everything you need. Love the bar on the first floor!
Guest favorite
A modern living area is showcased with a spacious grey sectional sofa and a round coffee table. A fully equipped kitchen with island seating can be seen in the background, along with large sliding glass doors leading to a private balcony that offers views of the surrounding landscape.
Apartment in Crozet
4.9 out of 5 average rating, 29 reviews

Piedmont Place 401| Lux Vineyard & Brewery Getaway

PerryRating, 5 stars6 months ago
We had a wonderful time. It was a great place to stay close to wineries and breweries.
Guest favorite
The living room features a sectional sofa with a cozy throw blanket, alongside a comfortable armchair. A coffee table is centered on a patterned area rug over hardwood flooring. Large windows are dressed with curtains, allowing natural light to brighten the space.
Apartment in Staunton
4.88 out of 5 average rating, 69 reviews

Big Blue #2: Spacious&Modern.

RyanRating, 5 stars1 month ago
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!
Top guest favorite
A welcoming living space features a gray couch adorned with orange and decorative pillows. A wall-mounted TV is positioned above a faux fireplace, complemented by a glass coffee table. A green accent wall and a patterned rug add character to the area, with wooden shelves displaying various items.
Apartment in Crozet
5 out of 5 average rating, 26 reviews

Mtn Vineyards Getaway

AdamRating, 5 stars1 day ago
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

Top guest favorite
A spacious living area features comfortable seating arrangements that include a sofa and armchairs. A traditional rug covers the wooden floor. A brick fireplace serves as a focal point, while soft lighting enhances the inviting atmosphere. A mirrored cabinet reflects the room's details.
Apartment in Staunton
4.94 out of 5 average rating, 381 reviews

The Attic in Restored Mansion Walk everywhere!

LauraRating, 5 stars1 week ago
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!
Top guest favorite
The exterior of a bright red barn-style building is showcased, featuring large windows that allow natural light to enter. A well-maintained lawn with small shrubs enhances the landscaping, while a staircase leads up to the entrance. The inviting setting is complemented by a clear blue sky.
Apartment in Crozet
5 out of 5 average rating, 484 reviews

The Barn at Haden near Wineries and C'ville

RachelRating, 5 stars1 week ago
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!
Superhost
Apartment in Afton
4.77 out of 5 average rating, 825 reviews

Studio Apt. in Wine/Brewery Country/on 151

AbigailRating, 5 stars1 week ago
This is my second stay at Sarah’s and I hope not my last. My dog loves the place and grounds too!
Guest favorite
An aerial view of a living and dining space reveals comfortable seating arranged around a wooden coffee table. A dining table is flanked by four chairs, positioned next to large windows that overlook a wooded area. Soft lighting adds to the cozy atmosphere.
Apartment in Wintergreen Resort
4.85 out of 5 average rating, 123 reviews

Walk to Market/Slopes!

JosephRating, 5 stars1 month ago
As advertised. Good location. Easy check-in
A spacious living area features a gray sofa and loveseat arranged around a coffee table. A soft area rug adds color to the hardwood flooring. A wall-mounted lamp and subtle artwork enhance the inviting atmosphere, complemented by natural light streaming from an adjacent window.
Apartment in Waynesboro
4.3 out of 5 average rating, 175 reviews

Minutes to BC Brewery BR Parkway 151 Wintergreen

EmmaRating, 5 stars1 month ago
This place was perfect for our short term stay! It had everything we needed. Would definitely stay here again.
Guest favorite
The exterior view of a two-story condo showcases a blend of brown and white siding, with large windows allowing natural light to enter. A wooden deck with steps leads to the main entrance, surrounded by greenery and a gravel pathway.
Apartment in Roseland
4.88 out of 5 average rating, 68 reviews

Close to Activities/Shops/slopeside

WilliamRating, 5 stars3 months ago
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!
A community playground is set amid lush greenery, featuring a wooden playset with multiple swings and a slide. A sandy area surrounds the play equipment, providing a safe surface for play. Picnic tables are visible in the background, surrounded by trees.
Apartment in Roseland
4.82 out of 5 average rating, 235 reviews

Spacious 2 bedroom, 2 bath condo w/ full kitchen

SusanRating, 5 stars5 months ago
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.
Superhost
A cozy seating area is presented, featuring a red couch adorned with a decorative pillow, positioned across from a wooden coffee table. A small bookshelf filled with books is visible beside a rustic wall with wood paneling, while artwork depicting a serene landscape hangs above.
Apartment in Afton
4.77 out of 5 average rating, 97 reviews

Earth Room Suite at Galleywinter Farm

ElizabethRating, 5 stars4 months ago
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

Destinations to explore