Apartment holiday rentals in Wintergreen Resort

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Popular amenities for Wintergreen Resort apartment rentals

Weekly apartment rentals

Guest favourite
Apartment 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 favourite
Apartment 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
Apartment 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 favourite
Apartment in Wintergreen Resort
4.93 out of 5 average rating, 61 reviews

Sitting on the 18th fairway

HeatherRating, 5 stars4 weeks ago
We absolutely loved our stay at the wintergreen resort. Jeff was an amazing host from start ro finsh. Highly recommend staying at the Wineglow. We look forward to staying there again.
Superhost
Apartment 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.
Guest favourite
Apartment in Wintergreen Resort
4.94 out of 5 average rating, 78 reviews

Cozy remodeled studio overlooking 18th hole

RoxanneRating, 5 stars3 months ago
Lovely stay for a quick ski trip at Wintergreen. Hosts were super kind and accommodating, and were also very helpful and responsive whenever we had questions. They have a lovely home that is clean, modern, and cozy, with everything you need for a healing and fun getaway in the mountains!
Top guest favourite
Apartment in Wintergreen Resort
5 out of 5 average rating, 15 reviews

Moutain Maison

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.
Guest favourite
Apartment 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!

Pet-friendly apartment rentals

Top guest favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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!!
Top guest favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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 favourite
Apartment 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!

Apartment rentals with a pool

Guest favourite
Apartment 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!
Apartment 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 favourite
Apartment 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 favourite
Apartment 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.
Apartment 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 favourite
Apartment 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.
Apartment 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 favourite
Apartment in Roseland
4.9 out of 5 average rating, 63 reviews

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

PeytonRating, 5 stars2 weeks ago
My wife and I really enjoyed a weekend getaway at Mikki’s place. The condo has a great location with beautiful views and access to nearby Wintergreen amenities, and we took advantage of the less than 20 minute drive to multiple of the Nelson 151 breweries. Mikki is very responsive and we appreciated her recommendations and help in getting us get access to a nearby pool. Would stay again!

Quick stats about apartment rentals in Wintergreen Resort

  • Total rentals

    310 properties

  • Nightly prices starting at

    ₹6,000 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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