Apartment holiday rentals in Wintergreen Resort

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Popular amenities for Wintergreen Resort apartment rentals

Weekly apartment rentals

Top guest favourite
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 61 reviews

Ty's Retreat: Cozy 2-bedroom condo with fireplace

AndrewRating, 5 stars2 months ago
Well appointed and exactly as pictures advertised. Very clean, cozy and quiet place for our family ski vacation. And bonus was Jon even being kind enough to have my daughters stuffed animal shipped to us after she left it behind! Highly recommend .
Guest favourite
Apartment in Wintergreen Resort
4.96 out of 5 average rating, 28 reviews

Pepper's Mountain Pad

KateRating, 5 stars2 months ago
An amazing host that was quick to respond and had great communication. The place was neat and easy and super close to Wintergreen Resort! Would book again!
Guest favourite
Apartment in Wintergreen Resort
5 out of 5 average rating, 14 reviews

Retreat @ 3 Ridges | 3min->Slopes | Walk to Dining

AnitaRating, 5 stars2 weeks ago
Very comfortable with easy parking for unloading. Well lit interior, lots of extras, bias games and books. Plenty of towels. Definitely enough space for a family or two couples.
Superhost
Apartment in Wintergreen Resort
4.88 out of 5 average rating, 67 reviews

Gorgeous Sunrises (The Cliffs)

AlyxisRating, 5 stars2 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
4.98 out of 5 average rating, 87 reviews

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br

MackenzieRating, 5 stars1 week ago
The place was super nice, honestly better than the pictures! Our group had a great time and all loved the place. Everything was super clean and organized. There was also a binder with local recommendations and we visited some of those restaurants and they were fantastic. I would definitely stay here again and recommend it to anyone.
Top guest favourite
Apartment in Wintergreen Resort
4.93 out of 5 average rating, 60 reviews

Minutes from the slopes

AlejandroRating, 5 stars2 months ago
Loved the living room view to the golf course, well equipped and Jeff was great!
Guest favourite
Apartment in Wintergreen Resort
4.95 out of 5 average rating, 19 reviews

Recently updated - view of the Blue Ridge Mtns

JenniferRating, 5 stars3 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 favourite
Apartment in Wintergreen Resort
5 out of 5 average rating, 23 reviews

Wintergreen condo near Nature Foundation & Spa

CourtneyRating, 5 stars2 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.

Pet-friendly apartment rentals

Top guest favourite
Apartment in Wintergreen Resort
4.97 out of 5 average rating, 126 reviews

Mtn/Firework Views from Private Deck ~ King Suite

AlyssaRating, 5 stars3 weeks ago
My fiance, our dog, and I had a wonderful stay at Susie's! The condo was well stocked with anything you may need during your stay. The dog bowls and towels were a thoughtful addition right as you walked in. The bed was comfortable and we loved having the TV up there to unwind after a day of hiking around nearby trails. We ended up having to reschedule the days that we were coming, and Susie made that process very easy. We will definitely be staying here again next time we come to 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 stars1 month 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, 86 reviews

Beautiful Mountain Getaway - Walk to Everything!

RachelRating, 5 stars2 months ago
Beautiful and well stocked condo. Perfect location, we could walk to everything on our ski trip. Wonderful and hospitable hosts!
Guest favourite
Apartment in Wintergreen Resort
4.91 out of 5 average rating, 166 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

DennisRating, 5 stars6 days ago
Cute 1 bedroom condo on top of the mountain at a ski resort. Would deff book again if looking for a place in area.
Top guest favourite
Apartment in Wintergreen Resort
4.98 out of 5 average rating, 228 reviews

Best View in the Blue Ridge from Biscuit's Porch

CassandraRating, 5 stars4 weeks ago
View is even more beautiful in person! We loved the balcony. Kitchen had everything we needed to make meals at home. Our pup loved the place too!
Guest favourite
Apartment in Wintergreen Resort
4.96 out of 5 average rating, 178 reviews

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

TimRating, 5 stars1 month ago
Lindsay’s place was perfect for our family’s ski weekend. The condo was spacious and had everything we needed. The views were amazing! Lindsay was a great communicator and very responsive host. Highly recommend!
Guest favourite
Apartment in Roseland
4.9 out of 5 average rating, 60 reviews

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

KevinRating, 5 stars2 weeks ago
Very lovely little home.
Top guest favourite
Apartment in Wintergreen Resort
4.94 out of 5 average rating, 246 reviews

Cozy, clean, quiet mountain condo- King bed

ChristieRating, 5 stars1 week ago
Ritta's condo is clean, spacious and comfortable, situated in a woodland sanctuary of peace and quiet. Loved each morning and evening of spacious solitude.

Apartment rentals with a pool

Guest favourite
Apartment in Wintergreen Resort
4.89 out of 5 average rating, 110 reviews

Blue Ridge Retreat: Your Cozy Mountain Getaway

TifanieRating, 5 stars2 weeks ago
The condo was cute and cozy. The listing is exactly what to expect. Ashley was responsive when we needed to communicate. Overall a nice stay for the price!
Apartment in Wintergreen Resort
4.78 out of 5 average rating, 94 reviews

Cozy Condo - Sleeps 4

DavidRating, 5 stars2 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, 18 reviews

On the mountain, pet and child friendly

ChrisRating, 5 stars3 weeks ago
Good place, everything was as described. Overlooks the golf course.
Guest favourite
Apartment in Wintergreen Resort
4.9 out of 5 average rating, 48 reviews

Wintergreen! Dog friendly, cozy and comfortable

RayRating, 5 stars1 month ago
Very cozy place, the owner was extremely responsive and very accommodating.
Guest favourite
Apartment in Wintergreen Resort
4.91 out of 5 average rating, 23 reviews

Wintergreen Mountain Views - Diamond in the Slopes

Ladd StephenRating, 5 stars1 month ago
Soooo glad we found this property! After checking in to another property that wasnt true ski in, ski out, we moved quickly to this property and we loved it! Modern, clean and comfy, games for kids, and amazing views! Hosts were responsive and very helpful you'll love this place!
Top guest favourite
Apartment in Wintergreen Resort
5 out of 5 average rating, 15 reviews

Moutain Maison

MargalitRating, 5 stars2 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.
Top guest favourite
Apartment in Wintergreen Resort
4.99 out of 5 average rating, 73 reviews

The Perfect Getaway-Cozy Condo for 2 to 4

JefferyRating, 5 stars1 month ago
This place was great for my family to go snowboarding. Conveniently located to wintergreen resort. The owners are great town to with and place was very clean.
Superhost
Apartment in Wintergreen Resort
5 out of 5 average rating, 3 reviews

Overlook 180 degree views w/Peloton!

GuyRating, 5 stars1 week ago
Great stay. Have stayed at Wintergreen many times before, but first time being higher up the mountain. Views are great. Huge porch, plenty of space. Nice layout. Kitchen clean with plenty of what you'd want. 2 bathrooms. Perfect size for our family of 2 adults and 1 teen. Would stay here again.

Quick stats about apartment rentals in Wintergreen Resort

  • Total rentals

    310 properties

  • Nightly prices starting at

    £52 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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