Apartment holiday rentals in Wintergreen Resort

4.99 out of 5 average rating, 159 reviews

Flat in Afton

Cozy stay with scenic views on a horse farmette

Cozy apartment with beautiful views on a horse farmette on the most scenic road in the county. Located within 15 miles from Charlottesville and only 6 miles from Shenandoah National Park and the Blue Ridge Parkway, this vacation rental is the perfect spot if you are looking for places to hike, scenic drives or visit the many wineries, breweries or cideries located in close proximity. The apartment is situated over the garage and has its own separate entrance offering guests plenty of privacy.

4.97 out of 5 average rating, 129 reviews

Bee & Key—Staunton downtown

Staunton (pronounced “Stanton”) is one of the most vibrant, charming small towns you’ll find anywhere, and Bee & Key is in the center of it. This bright and stylish apartment is on the second floor of a grand 1885 home on East Beverley St. You will be half a block from the restaurants and shops of our bustling downtown, including Blackfriar’s Playhouse, the Woodrow Wilson Museum, The Shack restaurant, and Mary Baldwin University. We’re an easy walk from Staunton’s historic Amtrak station.

Flat in Wintergreen Resort

4.93 out of 5 average rating, 135 reviews

Stone Ridge at Wintergreen

Get away to our cozy condo in the treetops. All of the comforts and conveniences of home. Enjoy our complimentary coffee, tea and hot chocolate bar. Snuggle up with a blanket on the large outdoor sofa or crank up the fireplace and play a board game. Challenge someone to a game of foosball or watch a movie with the kids. Treat yourself to a day at the spa or take the kids to the outdoor pool. Our place is within walking distance to the dog park. Great breweries, wineries and hiking nearby.

4.96 out of 5 average rating, 207 reviews

Georgetown on Church

We have filled our 1860s apartment with an eclectic collection of period antiques and original artwork, plus modern bathrooms with soapstone counters and rubber floors, and a large deck and flagstone courtyard for relaxing outdoors. This fully equipped apartment has everything you need and is conveniently located within walking distance to everything in downtown Staunton, with great light during the day, and a cozy romantic feel at night. A perfect getaway retreat for a weekend or a week!

5 out of 5 average rating, 123 reviews

Queen City Hideaway

Imagine waking up to stunning mountain views, brewing coffee on your private deck, and planning your day exploring Staunton's vibrant downtown. Fully stocked! Need for nothing! Unwind in the heart of Staunton's historic charm! Sip coffee on your private deck overlooking Staunton's vibrant cityscape and rolling mountains. Binge your favorite show on our smart TV, and whip up a meal in the stocked kitchen. Walk to restaurants, shops, or the theater. Book your stay today and start planning!

Superhost

Flat in Afton

4.87 out of 5 average rating, 332 reviews

Best Spot on the Wine/Brew Trail!

Charming, private, efficiency apartment located in the center of winery/brewery country! This efficiency offers fiber internet (super fast)! Less than a minute to Blue Mountain Brewery, Flying Fox Vineyard, and Valley Road Vineyard. Less than 5 minutes to Veritas Vineyard, Cardinal Point Vineyard, Silver Back Distillery, Afton Mountain Vineyards. 5-10 minutes to Bold Rock Cidery, Devils Backbone Brewery, Brewing Tree Brewery, Mountain Meadery, Hill Top Berry Farm, and so many more.

4.96 out of 5 average rating, 512 reviews

Little Yellow Hideaway (Apt in Historic Home)

We love our little imperfect home that creeks and looks pretty good for being over 100. Currently it is getting a makeover and upgrade. Please be aware of this as you are booking. It has a roomy, walkout basement apartment with windows in every room and is tucked away in the heart of downtown. This home dates back to the 1800s, with loads of character and occasionally a bit of noise from the upper levels. It’s not a high-end trendy spot, but it’s humble, and perfect in our eyes.

4.98 out of 5 average rating, 189 reviews

Flat in Rockfish

Blue Ridge Bliss - For family & friends to enjoy!

Welcome to Blue Ridge Bliss! Come enjoy the mesmerizing mountain top views of this well-appointed condo in The Ledges of Wintergreen Resort. It’s the perfect place to unwind, unplug and recharge. Whether here to ski, hike, or visit Virginia wineries, cideries, or craft breweries you’re sure to enjoy the beautiful views from the living room and deck. A short walk to The Highlands lift and across the street from the dog park, and picnic area it’s an ideal location.

4.94 out of 5 average rating, 167 reviews

Traveler’s Escape-1 bedroom. Walk to downtown!

Come stay with us at the Traveler’s Escape! A spacious clean and unique ground floor apartment. Modern decor but everything you will need for a comfortable stay. Walk to the heart of historic downtown Staunton. Spend your days enjoying history, wineries, breweries or a beautiful drive to Shanadoah national park, only a 20 min drive . We provide a couch that converts to a third person sleep space in the living room. We allow pets upon approval

4.97 out of 5 average rating, 255 reviews

⭐Private Apartment Footsteps From Downtown

Our home is an 1890's Victorian in Staunton's Gospel Hill Historic District. It is walking distance from everything in Downtown Staunton. We have a private apartment with its own separate entrance. 1 bedroom, 1 bath, comfortably furnished with kitchenette, high speed WiFi and Smart tv. Just 2 blocks from Shakespeare Blackfriars Theatre, VA School for the Deaf and Blind, Woodrow Wilson Birthplace, and renowned local restaurant 'The Shack'.

4.98 out of 5 average rating, 331 reviews

The Bons Amis Suite: Walk Downtown!

The Bons Amis Suite means “The Good Friends Suite” in French. It has been lovingly furnished, decorated, and named in honor of owners Kati and Keith Hebert’s dear friends, Thierry and Sandrine and their family, who live in Tours, France. Thierry and Sandrine owned the first Airbnb that our owners ever stayed in! This suite is a comfortably elegant and serene private apartment on the upper level of this renovated two-story Victorian home.