House vacation rentals in Wintergreen Resort

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Popular amenities for Wintergreen Resort house rentals

House rentals with a hot tub

Top guest favorite
Home in Afton
4.97 out of 5 average rating, 155 reviews

The Inn at Blue Mountain Brewery

CarolineRating, 5 stars1 month ago
This was a perfect two night getaway with our family. The house is very clean. The views are beautiful. There are lots of things to do in the area not far from the house. We enjoyed taking the short path to the brewery for a couple of meals. The food is great! We sat by the fire and soaked in the hot tub. Martha’s instructions were very easy to follow to check in and checkout. She was very responsive. We appreciate that she also offered plenty of suggestions for things to do in the area. Thank you, Martha! We look forward to our next visit. Caroline
Top guest favorite
Home in Crozet
4.97 out of 5 average rating, 198 reviews

Crozet casa w/ firepit & hot tub in wine country

AlexanderRating, 5 stars4 weeks ago
Not only was the house and property fantastic, but the responsiveness and support from the hosts before/during/after was top notch. Everything went smooth with the entire stay, and we'd highly recommend.
Guest favorite
Home in Wintergreen Resort
4.92 out of 5 average rating, 50 reviews

Whispering Creek Hot Tub Pool TennisGolf King Beds

JohnRating, 5 stars1 month ago
The stay was wonderful. Our family felt right at home and really enjoyed the dining room, the hot tub and the backyard.
Guest favorite
Home in Wintergreen Resort
4.89 out of 5 average rating, 63 reviews

Hot Tub EV Charger Mntn View Fireplace Grill Pool

ShyamRating, 5 stars2 months ago
Great place to stay for a weekend of skiing!
Guest favorite
Home in Roseland
4.89 out of 5 average rating, 28 reviews

Mountain retreat with hot tub

ThomasRating, 5 stars2 months ago
Perfect getaway for wintergreen! Great house, plenty of space. Fireplace and hot tub were perfect for those cold nights. There is an amazing overlook just up the road that’s perfect for panoramic Mountain View’s.
Superhost
Home in Afton
4.91 out of 5 average rating, 101 reviews

Fox Hill: 151 Cottage w/Hot Tub + Mountain Views

KristinaRating, 5 stars1 week ago
Very happy with our stay. Beautiful mountain drive.
Superhost
Home in Lyndhurst
4.78 out of 5 average rating, 9 reviews

Cabin #10 · Cabin #10 · Sherando Cabin-3+ BR, hot

SergioRating, 5 stars20 months ago
It's a great place to stay, a very quiet place, close to the lake. Dogs loved too, plenty of space for them to play around. The house is clean, spacious, cozy fireplace and a wonderful hot tub. Owners are courteous and friendly, certainly recommend it!
Guest favorite
Home in Wintergreen Resort
4.98 out of 5 average rating, 47 reviews

Super Comfy Mtn Escape w/ 4 Bedrooms & Hot Tub

KennethRating, 5 stars1 month ago
Our stay was outstanding. There were 6 adults, 3 grandchildren and 3 dogs and we all had plenty of room. The bedrooms were spacious and comfortable. We enjoyed the fire pit and the grandchildren loved the jacuzzi.

House rentals with a pool

Guest favorite
Home in Wintergreen Resort
4.88 out of 5 average rating, 135 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

KatieRating, 5 stars1 month ago
We had the absolute best time staying here. We had two families staying together, 10 total. With more than enough space! The location was perfect. The space was clean and cozy. We had the best time and made some amazing memories with our friends. Also we slept at night on the third floor with a window opened and it was so quiet outside! Thank you for opening your home to us!
Top guest favorite
Home in Lovingston
4.96 out of 5 average rating, 207 reviews

Cottage on the Knoll ~ (Private Pool & Hot Tub)

RachelRating, 5 stars3 weeks ago
Loved our work retreat at Bobbi’s place. Nearby goats were fun & friendly neighbors noting our comings & goings. The kitchen was well appointed with stainless steel pots and an induction stove. Ahhh, the hot tub and ping pong table: perfect amenities we turned to for winding down after intensive work. Stunning begonia (a REAL one) @ the front door welcomed us in beautifully! And Bobbi is a caring host! He responds lickety split to messages and went beyond the call to contact animal control when a guest’s boot mysteriously disappeared from the porch. Thanks, Bobbi!
Guest favorite
Home in Afton
4.94 out of 5 average rating, 141 reviews

Farmhouse on Working Vineyard

KatyRating, 5 stars6 months ago
Susan’s farm house was perfect for enjoying a relaxing getaway with plenty of space for multiple families and kids. All of the spices are very large and honestly it’s better in person than in the pictures. We would recommend it to anyone and return again! The kitchen was nicely stocked with everything you could need. And it was great being right on the winery.
Top guest favorite
Home in Wintergreen Resort
4.93 out of 5 average rating, 58 reviews

Wintergreen Condo~ 1 Minute To Four Seasons Resort

KristenRating, 5 stars2 months ago
Great location next to slopes and restaurants! Easy to get to, park out front and easy access to enter. Cozy and comfortable inside and everything available we would need for the weekend. Appreciated the plentiful firewood right out front. We enjoyed our stay and hope to be back in the summer! Thank you for sharing your mountain condo with our family!
Top guest favorite
Home in Crozet
5 out of 5 average rating, 11 reviews

Stunning Mt Views, Pool | near Vineyards & UVA

ErinRating, 5 stars1 week ago
We loved our stay! The house was beautiful and so thoughtfully appointed. The kids loved the pool and running around outside, the views were beautiful, and Sarah was such a welcoming host. We are looking forward to coming back!
Guest favorite
Home in Wintergreen Resort
4.96 out of 5 average rating, 105 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

NikiRating, 5 stars1 week ago
Our family of four needed a quiet get away, and we enjoyed the beautiful days and evenings, inside and on the deck! Hikes nearby, spa nearby, restaurants, grocery, gas also nearby. Great resort year round! Lots of activities if you want them, and lots of peaceful nature if you want. Great!
Guest favorite
Home in Wintergreen Resort
4.96 out of 5 average rating, 105 reviews

Bear's Mountain Escape

LizRating, 5 stars2 weeks ago
Lovely spot in the mountains! Perfect if you're planning to hike! The space was cozy and clean; we brought our two dogs and had fun all sitting by the fire inside! It was thoughtful of her to have laundry detergent pods for us to use. The master bed was comfortable, which I don't find myself saying too often in Airbnbs! Overall, it was peaceful and quiet - a great getaway from the city.
Guest favorite
Home in Wintergreen Resort
4.82 out of 5 average rating, 158 reviews

Misty Mountain Cabin w/spa

LeslieRating, 5 stars3 weeks ago
Beautiful space to spend a weekend with friends. Lovely views from each room and the deck. Walkable hiking trails with waterfalls. Would stay here again.

Weekly house rentals

Top guest favorite
Home in Wintergreen Resort
4.96 out of 5 average rating, 103 reviews

Cliffs Edge Memorial Weekend & Summer Camp

MatthewRating, 5 stars2 weeks ago
Julie was a great host and very communicative. The house was clean and looked exactly like the pictures. We loved the views and the layout of the house - it is perfect for a weekend getaway in the mountains.
Guest favorite
Home in Waynesboro
4.97 out of 5 average rating, 35 reviews

Waynesboro Stay Near Wintergreen & Charlottesville

ChanceRating, 5 stars4 months ago
The house was in excellent condition and was exactly what we were looking for on our trip. Joshua was a wonderful host and was quick to respond.
Top guest favorite
Home in Wintergreen Resort
4.95 out of 5 average rating, 39 reviews

Welcome to Winterhaven! 5BR/4BA .5mi from lodge!

LourdesRating, 5 stars2 days ago
Myself and 6 of my closest friends, all women, had a wonderful time at Neal's house. The place was spotless, very private and very comfortable and it was an easy drive to downtown Charlottesville.
Superhost
Home in Wintergreen Resort
4.95 out of 5 average rating, 56 reviews

Beautiful Wintergreen! Over 3800 sf.

GailRating, 5 stars2 months ago
Alvin and Aimee’s place was wonderful!! The space inside and the views outside were great. Not avid skiers but we enjoyed going to the resort and watching our adult children snow boarding. The parking area gets pretty crowded on the weekends but it wasn’t an issue for us. The property had a couple of small issues but communication with the hosts were swift, easy and quickly addressed. Their property manager was on hand and was one of kindest gentlemen we met. If you are looking to visit the Wintergreen Resort area, book this property…. You will not be disappointed!!!
Superhost
Home in Wintergreen Resort
4.88 out of 5 average rating, 16 reviews

Spring Special $125 Sun-Thu $165 Fr-Sat Pets ok

ChrisRating, 5 stars2 weeks ago
Perfectly suited the needs for our small family. Cozy feel. Exactly what we wanted for our mountain getaway. Good instructions both through Airbnb and a binder. Outdoor and screened porch was great.
Guest favorite
Home in Afton
4.96 out of 5 average rating, 241 reviews

CritzerHouse - on 151- Walk to the Brewery!

KarenRating, 5 stars1 week ago
We had a great stay at the Critzer House. It was just as described and perfect for our two families of four. Plenty of room for all of us to hang out together or retreat to separate spaces for some quiet time. The sunroom was great for starting the day with coffee and finishing with adult beverages. The location was ideal...30 minutes or less to incredible hikes, breweries, wineries, and distilleries. Easy walk to Blue Mountain Brewery for dinner after a long day exploring the beautiful surrounding area.
Guest favorite
Home in Staunton
4.91 out of 5 average rating, 138 reviews

Little Yellow House: Walk to Downtown Staunton

MeredithRating, 5 stars1 week ago
We loved our stay! This was the perfect space and spot for a trip to explore everything downtown Staunton has to offer, as well as the surrounding natural beauty. The place was clean and adorable. We loved how all of the character of such an old building was the star of the space, but was updated to make it comfortable. The washer and dryer was great convenience to have! Very quiet and easy to use. The location was PERFECT! Our family included myself, husband, two teens, and two dogs. We all could stretch out. I will miss morning coffee with the many birds to watch on the back porch!
Guest favorite
Home in Staunton
4.98 out of 5 average rating, 65 reviews

Gypsy Hill Cottage ~Park Views, Near Downtown

DaleRating, 5 stars2 weeks ago
Great location for our stay. Walkable distance to downtown great fenced in backyard for our dog and toddler. An amazing park directly across the street beautiful area. Definitely would stay here again.

Quick stats about house rentals in Wintergreen Resort

  • Total rentals

    220 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    7.7K reviews

  • Family-friendly rentals

    220 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    110 properties have a pool

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