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Condo vacation rentals in Wintergreen Resort

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Popular amenities for Wintergreen Resort condo rentals

Weekly condo rentals

Guest favorite
A cascading waterfall flows over rugged, moss-covered rocks, creating a serene scene. Surrounding trees are bare, indicating a transition between seasons. Water splashes and streams down, framed by the natural stone formations and earthy tones of the landscape.
Condo in Wintergreen Resort
4.85 out of 5 average rating, 67 reviews

Fireworks & Mountain Views Ski In/Out Studio in WG

MatthewRating, 5 stars3 months ago
This is the perfect place for a couple looking to take advantage of the resort. It’s super easy to find and the access to the slopes couldn’t be better. It literally took us minutes to walk to restaurants, rentals, lifts, etc. It was so calming to look out at the mountains and ski runs. The AC/Heat unit provides nice white noise if you like sleeping to that. It was perfect for us and we’ll come back next time.
Guest favorite
Condo in Massies Mill
4.92 out of 5 average rating, 24 reviews

Mountain Top Getaway

SarahRating, 5 stars1 month ago
This condo in the Wintergreen resort is so peaceful and beautiful. It was a great size for our family of 4 plus my in-laws. 3 full bathrooms was great! The drive up and down the mountain took some getting used to but the views are amazing at the top! The primary bedroom is bright in the morning sun so bring a sleep mask if you want to sleep in.
Guest favorite
A sweeping mountain view captures rolling hills and expansive skies, transitioning from vibrant green foliage to soft, colorful clouds. The landscape showcases a blend of open fields and dense trees, offering a serene atmosphere characteristic of the mountains.
Condo in Wintergreen Resort
4.87 out of 5 average rating, 23 reviews

Condo w/ Full Kitchen, Balcony, King & Queen Beds

JoanneRating, 5 stars1 month ago
Loved this place! Easy to find (saying a lot for Wintergreen...not always so easy!) with beautiful peaceful surroundings, and lovely amenities in a comfortable, clean & quiet place. Mary was super responsive to our questions. We recommend it!
Superhost
A detailed map of Wintergreen Resort illustrates various facilities and accommodations. Locations are marked with symbols indicating dining, lodging, and recreational areas. Pathways and road systems are presented, offering a clear layout of the resort for easy navigation.
Condo in Wintergreen Resort
4.88 out of 5 average rating, 67 reviews

Gorgeous Sunrises (The Cliffs)

AlyxisRating, 5 stars3 months ago
We spent the weekend here to go snowboarding. It was very walkable to drop in at highlands or wait for the shuttle. Check in was easy and the kitchen was amazing. The view was incredible.
Top guest favorite
The living room features a comfortable sofa and stylish armchair, arranged around a wooden coffee table. A cozy fireplace is visible, with the flames flickering. Large windows allow natural light to fill the space, with a view into the adjacent dining area, which includes a high-top table.
Condo in Wintergreen Resort
4.99 out of 5 average rating, 89 reviews

Stylish*Updated*Central*Walk to Slopes*Dogs OK!

AndyRating, 5 stars1 week ago
Had a great stay. We will definitely be back. First time visiting Wintergreen and loved the area.
Guest favorite
A scenic balcony view displays a vibrant sunset over the rolling mountains, with layers of hills fading into the horizon. A round metal table with chairs is positioned on the deck, inviting relaxation while enjoying the natural beauty.
Condo in Wintergreen Resort
4.97 out of 5 average rating, 37 reviews

Breathtaking Views from The Ledges

LoganRating, 5 stars4 months ago
house was very well stocked for an Airbnb (games, kitchen stuff, household items, etc), having an onsite firewood supply was amazing as was being within walking distance of some of the slopes. Vivian's instructions were very clear on the check in/check out procedure and everything was described accurately. Would stay here again!
Superhost
A cozy living room features a comfortable seating arrangement with plush chairs and a sofa. Large windows allow natural light to fill the space, enhancing the view of the surrounding greenery. A coffee table is placed centrally, surrounded by decorative plants.
Condo in Wintergreen Resort
4.79 out of 5 average rating, 71 reviews

Wintergreen Best location,Arcades,king bed,2 room

LindaRating, 5 stars5 days ago
I stayed a month at Carlos’s beautiful condo. It felt like the woods and golf course were within arm’s length due to the large windows along two walls. I could tell that a lot of planning went into equipping the kitchen. In addition to the coffee makers and toaster, two of my favorite items were available. A blender and a very fast water heater for a quick cup of cocoa. Everything was spotless with plenty of towels and linens. I was very comfortable and the neighbors were very friendly. I only had one incident of getting locked out due to a maintenance crew error. I was shocked at how fast Carlos responded to my message and within 10 min. I was back in the condo. Amazing communication! I would not hesitate to stay there again. It would be stunning in the winter too with the cozy fireplace. Carlos is the perfect host.
Top guest favorite
A wooden deck extends from the tan-colored building, surrounded by snowy landscapes and bare trees. The roof is blanketed in fresh snow, creating a serene winter ambiance. Large windows reflect the natural light, contributing to the inviting exterior view.
Condo in Wintergreen Resort
5 out of 5 average rating, 15 reviews

Mountain House

MargalitRating, 5 stars3 months ago
Great one bedroom condo with cozy but spacious living room and bedroom. Best highlight is that it is about a 7 minute walk to the slopes and the small resort village for wintergreen. Perfect spot for a getaway.

Pet-friendly condo rentals

Top guest favorite
An inviting living space features a comfortable sectional sofa arranged around a round coffee table, complemented by a cozy rug. A gas fireplace is framed by white paneling, and large windows provide ample natural light while showcasing views of the surrounding landscape.
Condo in Wintergreen Resort
4.95 out of 5 average rating, 131 reviews

All-Season 2bd/2ba next to Spa view of Golf Course

StaceyRating, 5 stars1 month ago
We stayed here for my daughter’s college graduation and couldn’t have asked for a better spot. The condo was exactly as described—clean, comfortable, and perfect for our family of four. We didn’t spend much time there (graduation weekends are a blur), but it had everything we needed. It’s about an hour from Lynchburg, Virginia, and the location was ideal for us. Quiet, convenient, and a great fit for our weekend plans. The host was wonderful—responsive, flexible, and easy to communicate with. They helped us adjust our reservation and answered all our questions before and during our stay. I have nothing but praise. Highly recommend if you’re looking for a well-kept, stress-free place to stay.
Guest favorite
Two reclining chairs are positioned in a cozy living area, complemented by a warm orange wall. A dining area with a wooden table is visible in the background, along with large glass doors that provide natural light and access to a terrace overlooking greenery.
Condo in Wintergreen Resort
5 out of 5 average rating, 20 reviews

On the mountain, pet and child friendly

Mary KayRating, 5 stars3 weeks ago
Perfect cozy getaway with beautiful views. Great location within walking distance to golfing, Nature Center, pool, spa & food.
Top guest favorite
The two-story condo features a warm wood exterior, framed by lush greenery and trees. Wide wooden steps lead to the entrance, giving access to individual balconies that enhance the inviting appearance of the building.
Condo in Wintergreen Resort
4.95 out of 5 average rating, 295 reviews

Five Minute Walk to Everything!

CarolynRating, 5 stars2 weeks ago
This place was great! Conveniently located with tons of things to do, many walkable from the condo. The photos and descriptions were super accurate and our dogs even felt welcomed! We appreciated the convenience of The Market, The Edge, Upper Crust, and really enjoyed all of the Memorial Day activities that Dave ad Paige let us know were happening. It was the perfect place to unwind after a day of adventuring. Dave and Paige were super hosts all the way around. We'd love to come back here again!
Top guest favorite
A spacious living area features a comfortable sofa, a wooden coffee table, and a well-lit dining space. Large windows allow natural light to fill the room, and a fireplace adds warmth. Colorful artwork adorns the walls, complementing the light-toned flooring.
Condo in Wintergreen Resort
4.9 out of 5 average rating, 49 reviews

Wintergreen! Dog friendly, cozy and comfortable

ColleenRating, 5 stars1 month ago
We had a fantastic weekend at Kim’s place. It was the perfect size for me, my husband, our daughter, and small dog. We enjoyed the balcony and the fireplace. Kim was super responsive and suggested local attractions. It was wonderful to unplug and be in the woods for a few days. Highly recommend!!
Guest favorite
The living area features comfortable leather seating arranged around a wooden coffee table. A fireplace is visible, surrounded by a stone accent, and large windows allow natural light to fill the space, offering views of the outdoors.
Condo in Wintergreen Resort
4.88 out of 5 average rating, 113 reviews

1720 High Ridge at Wintergreen Resort

HuntRating, 5 stars3 months ago
Beautiful location with the daily sunrise over the blue ridge mountains is captivating. Kimberly who manages the property is the provides the best customer service I've ever had at Air B&B . (Got well over 100 nights in withAirB&B)
Guest favorite
A deck features two comfortably arranged chairs with cushions, overlooking expansive views of the Blue Ridge Mountains. Clear skies are visible, and the natural landscape extends into the distance, highlighting the serene outdoor setting.
Condo in Wintergreen Resort
4.95 out of 5 average rating, 20 reviews

Recently updated - view of the Blue Ridge Mtns

JenniferRating, 5 stars5 months ago
This condo was perfect for a long ski weekend for our family of 4. Located close to slopes, clean and with a spectacular view! Would definitely stay again!
Guest favorite
The main living area features a new sectional sofa facing a stone fireplace with a mounted TV above. A coffee table is positioned centrally, while light fills the room through large windows. The space is designed with soft carpeting and built-in shelving.
Condo in Wintergreen Resort
4.97 out of 5 average rating, 87 reviews

Beautiful Mountain Getaway - Walk to Everything!

HelenRating, 5 stars1 month ago
We were attending a graduation in Lynchburg and this place was perfect for our large party (7 adults, 1 toddler, and 3 dogs). It’s clean and very kid friendly, had everything we needed for our stay. The host was a great communicator and very accommodating to our schedule. We appreciate the flexibility! Will definitely stay here again!
Guest favorite
The living room features a spacious sectional sofa and two armchairs, arranged around a wooden coffee table. A wood-burning fireplace is located against a green wall, complemented by softly illuminated shelves. Natural light filters through windows, creating a cozy atmosphere.
Condo in Roseland
4.9 out of 5 average rating, 62 reviews

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

LindseyRating, 5 stars4 weeks ago
We really enjoyed our stay at Mikki's for three nights over the weekend of our son's college graduation. Though the travel to Lynchburg for the ceremonies was a touch over an hour one-way, the drive was mostly scenic, especially once you hit Patrick Henry Hwy. Honestly, any closer to Lynchburg we would have paid a lot more money, but Mikki's rates were very reasonable, especially given the scenery and surroundings, as well as proximity to many outdoor adventures, which we had no time to explore. If you are staying in the area for any length of time, this is a great getaway, as there's much to do and see. Unfortunately, we were there mostly to sleep and to have coffee in the morning, before we had to be on our way, but no regrets. It was a great place and we would recommend! The host was very communicative and accommodating, which we appreciated very much.

Condo rentals with a pool

Guest favorite
The exterior of the mountain condo is displayed, featuring a brown wooden structure with a steeply pitched roof. A wooden walkway leads to the entrance, bordered by low greenery. Large windows adorn the upper level, providing natural light. The setting is surrounded by trees, indicating a tranquil environment.
Condo in Wintergreen Resort
4.97 out of 5 average rating, 29 reviews

Pepper's Mountain Pad

AbbeyRating, 5 stars2 weeks ago
Don't skip over this perfect spot. One thing I loved most was that even though it is dog friendly nothing in the place smelled like dogs or had any odor. There were no stains on furniture. It was also perfectly cleaned. The beds were comfortable the bathrooms were spacious. We loved the back patio facing the trees. It was also a nice patio with only a few steps down to ground to make it easy to let the dogs out. The pull out couch was comfortable. I would stay again and again here. I've stayed several places in wintergreen and this cozy place and great location can't be beat!
An open living area features a sectional sofa in light grey, arranged around a round wooden coffee table. A sleek black television is mounted above a modern fireplace. Large windows provide natural light, while a ceiling fan and wall art enhance the space.
Condo in Wintergreen Resort
5 out of 5 average rating, 3 reviews

Uncork and Unwind! Perfect Mountain Retreat

NicRating, 5 stars3 months ago
We were looking for a nice getaway as a family to go skiing and Brian’s place was a perfect spot. Everything was as described. Especially liked the wood burning fireplace and being able to walk to the ski slopes and ride. The kitchen was neat and had everything we needed. The Market is steps away for any conveniences’s or breakfast sandwich and coffee. We’d love to come back again soon.
Guest favorite
A spacious living area is furnished with a comfortable couch adorned with multiple pillows. A wooden coffee table sits on a textured rug, complemented by a small side table with a plant. Bright light emanates from a floor lamp, while a ceiling fan provides air circulation.
Condo in Wintergreen Resort
4.89 out of 5 average rating, 112 reviews

Blue Ridge Retreat: Your Cozy Mountain Getaway

SamuelRating, 5 stars4 weeks ago
If you like hiking and being outdoors, this is a great spot. You can be on blue ridge parkway/skyline drive in less than 20 minutes. There are many options for hiking trails nearby, pretty quiet area during the week as well. Ashley is pretty quick to respond to any questions a person may have and was helpful, besides her binder of things to do. However, if you’re looking for a place with Mountain View’s out of the windows this one doesn’t have that, but it is close by driving wise.
Guest favorite
A cozy living area features a light-colored sofa with decorative cushions. A wooden coffee table sits in front, accompanied by an accent chair. A fireplace is positioned against the wall, and large windows allow natural light to illuminate the space, overlooking lush greenery.
Condo in Wintergreen Resort
4.9 out of 5 average rating, 49 reviews

2 br/2 b condo; skiing; hiking; wineries; pool

JamesRating, 5 stars3 months ago
This was a getaway to see our kids, and it was perfect. Amanda went out of her way to accommodate our needs, and her place is a great refuge. What really stands out is how communicative she was in every step from booking, to questions, checkin, and checkout. Everything went super smoothly and we enjoyed our stay.
A shared pool area is surrounded by a spacious deck, equipped with several lounge chairs. Tall trees provide a natural backdrop, and the clear water of the pool reflects the surrounding greenery. A pathway and other condo buildings are visible in the distance.
Condo in Wintergreen Resort
4.78 out of 5 average rating, 94 reviews

Cozy Condo - Sleeps 4

DavidRating, 5 stars3 months ago
Great location! So so much fun! Thank you for such a great stay!
Guest favorite
The exterior of the condo is framed by tall trees, with a covered deck featuring a wooden railing. A flag is displayed prominently, and large windows allow natural light to brighten the interior. The surroundings reflect a natural and inviting atmosphere.
Condo in Wintergreen Resort
5 out of 5 average rating, 23 reviews

Wintergreen condo near Nature Foundation & Spa

CourtneyRating, 5 stars4 months ago
We've stayed in a lot of condos in Wintergreen over the years, and this may be one of my favorites. This was a very comfortable two bedroom / two bathroom. It was a perfect size for our group of 2 adults and 2 teens. The furnishings were very nice. It is easy to get into (first floor). The view is of the woods behind the condo and quiet. Also, we appreciate how responsive the host was! She quickly returned our call in the evening when we had a little trouble getting into the lock code. Her instructions had been perfect; we just made a mistake with the code. We should have brought a little dishwashing detergent. There was one pod there. I'd stay there again.
A spacious balcony offers outdoor seating with a glass-top table and four metal chairs. Expansive mountain views extend beyond the boundary, showcasing rolling hills under a clear blue sky.
Condo in Wintergreen Resort
4.53 out of 5 average rating, 83 reviews

Amazing views! Overlooking Expert Slope

AlexisRating, 5 stars3 months ago
Great place! We love this area of Wintergreen. Willette’s place was clean and had all we needed. Communication was excellent. We would definitely stay again.
Guest favorite
A spacious bed is dressed in plaid and textured bedding, accompanied by a decorative fern in a ceramic pot on a wooden nightstand. Soft lighting illuminates the serene atmosphere, enhancing the restful setting.
Condo in Wintergreen Resort
4.92 out of 5 average rating, 63 reviews

Views & Brews with 2 Floors

NancyRating, 5 stars2 weeks ago
The view from both levels of this spotless, comfortable condo was as breathtaking in person as it was in the photos. This was the perfect place for our family to celebrate our daughter's graduation. Then, we left so she and her husband could have a mini vacation there by themselves. Dave & Rebecca responded immediately to my questions and were proactive about extending our stay. Our daughter and her husband were thrilled to have another night there. We will definitely be back, hopefully in every season!

Quick stats about condo rentals in Wintergreen Resort

  • Total rentals

    310 properties

  • Nightly prices starting at

    G$14,689 GYD before taxes and fees

  • Total number of reviews

    9.8K reviews

  • Family-friendly rentals

    180 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    240 properties have a pool

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