
House vacation rentals in Wintergreen Resort
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Top-rated house rentals in Wintergreen Resort
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Popular amenities for Wintergreen Resort house rentals
House rentals with a hot tub

The Inn at Blue Mountain Brewery
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

Crozet casa w/ firepit & hot tub in wine country
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.

Whispering Creek Hot Tub Pool TennisGolf King Beds
We came for a sister trip and had a fabulous time. We had to drag ourselves out of the jacuzzi to visit a few wineries. Everything was great from the accommodations to Charlotte, who was so amazing with suggestions. We loved the location and would definitely come again. Much fun was had!

Hot Tub EV Charger Mntn View Fireplace Grill Pool
Had a fantastic wonderful family time. Very peaceful location and this April time of the year was perfect for a quiet getaway. Hot tub was very enjoyable, as was family time around the gas fire pit on the deck, and inside at the fireplace. Host was very quick to respond to questions. Everything was as we expected. The views and being on top of the mountain were memorable. Breweries. Wineries, Distilleries, eating places and grocery markets all within short drives. We would definitely stay here again! Thank you Hosts for making this special home available through Airbnb!

Mountain retreat with hot tub
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.

Fox Hill: 151 Cottage w/Hot Tub + Mountain Views
Very happy with our stay. Beautiful mountain drive.

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

Super Comfy Mtn Escape w/ 4 Bedrooms & Hot Tub
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

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat
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!

Cottage on the Knoll ~ Prvt Pool & Hot Tub OPEN
Three couples wanted a central meeting place to spend some quality time catching up with each other. It was just the perfect place! We had a nice time talking in the hot tub, around the fire on the cozy porch, and in the exquisite pool. The goats added a nice touch to this country setting. The kitchen had all the cooking supplies we needed and more. We did a good bit of eating onsite so that was appreciated. We unfortunately didn’t use the pingpong table or other games but they were there to enjoy. There were plenty of towels and the new washer and dryer were great. It’s a great location to experience the many local wineries. Bobbi and Keith were excellent hosts, friendly and gave great suggestions of things to do. Everything about our stay was wonderful. We hope to return soon!

Farmhouse on Working Vineyard
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.

Wintergreen Condo~ 1 Minute To Four Seasons Resort
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!

Stunning Mt Views, Pool | near Vineyards & UVA
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!

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

Bear's Mountain Escape
We enjoyed your home so much! It was pet friendly but we didn’t need that because we were able to accommodate our dogs with a family friend but that was a huge selling point for us. You would not know it was a dog friendly place - usually you can tell! All the extras were amazing - we look forward to coming again soon!

Misty Mountain Cabin w/spa
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

Cliffs Edge Memorial Weekend & Summer Camp
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.

Waynesboro Stay Near Wintergreen & Charlottesville
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.

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

Beautiful Wintergreen! Over 3800 sf.
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!!!

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

CritzerHouse - on 151- Walk to the Brewery!
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.

Little Yellow House: Walk to Downtown Staunton
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!

Gypsy Hill Cottage ~Park Views, Near Downtown
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
$90 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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