
Pet-friendly vacation rentals in Wintergreen Resort
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Top-rated pet-friendly home rentals in Wintergreen Resort
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Popular amenities for Wintergreen Resort pet-friendly home rentals
Pet-friendly home rentals with a hot tub

Ultimate cabin in the mountains
What a great experience! The location is secluded enough for the privacy we wanted, yet near plenty of enjoyable towns and establishments. It was really convenient for us to be about 40 mins from Charlottesville and 50 mins from Staunton. Andrew's cabin is really spacious without losing its coziness. It's rare to find an Airbnb that's stocked with everything you need, and this place checked all of the boxes for us. We never wanted to leave, which is always a good sign. For that reason, we will be back!

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.

Mountain Season Lodge
My family had a wonderful time staying at this beautiful house. It was a perfect fit for us. There was plenty of room for everyone and we had a great time playing cards in the evening and watching movies. My 4 and 2 year old grandsons looked forward to going to bed at night so they could take a bath in the jacuzzi tub. The house had everything you could possibly want. The hot tub was a hit with my grown children. We look forward to returning in the future.

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!

The Cottage at Spindle Hill: an Artist’s Farm
This place is absolutely delightful! The farm is beautiful and peaceful. The cottage was gorgeous and cozy. Loved the art and other homey touches. We had a great time hammocking and using the hot tub. If you feel like spending some time away from the cottage (you may not) there are lots of trails, breweries and wineries nearby. It’s an ideal spot for reading, sipping coffee and relaxing. I really don’t think place could get any more perfect. I would highly recommend it and hope to come back soon.

Hot Tub DogsOK Grill Fireplace Pac Man Pool Tennis
Great place in Wintergreen! We stayed in Spring and everything was quiet and the foliage was vibrant. Our family went hiking and exploring everyday, and enjoyed the food and drink down in the valley. There is a nice trail in Wintergreen if you can find the overlook off Old Appalachian trail. Hot tub was a plus for sure! Enjoyed the trails in the neighborhood and watching the golfers. All the amenities you could ask for and a clean tidy home!

Luxury Mountain Lodge w/ Hot Tub & Stunning Views!
My children and I had such a wonderful time at the lodge. The view is priceless. We enjoyed each and every day and hated to leave. The beautiful outdoor deck with amazing views, the hot tub, the wall of windows with the very best Mountain View and the game area downstairs were all highlights for us. We appreciated and took advantage of the local recommendations and can’t wait to return. Lauren was a wonderful host and answered all of our questions immediately throughout the stay. We hope to be back!

Fox Hill: 151 Cottage w/Hot Tub + Mountain Views
Very happy with our stay. Beautiful mountain drive.
Pet-friendly home rentals with a pool

Mtn/Firework Views from Private Deck ~ King Suite
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!

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.

The Bear Dance Cabin at Wintergreen Resort
I’d argue that this is one of the best places to stay in Wintergreen. The cabin itself is perfect. We are a young family and it was comfortable, clean, and had everything we needed. The location is also perfect. It is very close to all the attractions on the resort. Clay was a great host as well. The perfect amount of communication; engaged without being intrusive. I would recommend this place to anyone who wants to be sure their trip is easy and successful!

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!

Tips Up: Cozy Slopeside Retreat w/ Fireplace
Cute 1 bedroom condo on top of the mountain at a ski resort. Would deff book again if looking for a place in area.

Blue Ridge Bliss - For family & friends to enjoy!
The condo was easy to find and close to the parking lot. Upon entering, the view off the balcony was stunning. Worth the early morning to watch sunrise on a good day. The wood burning fireplace adds a nice cozy touch. Loved everything about the place and the lovely hosts. It’s an easy walk to a fenced dog park and a small restaurant in the wintergreen resort area.

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

Cozy, clean, quiet mountain condo- King bed
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.
Pet-friendly house rentals

“Small" House/Peaceful/Breweries/Hikes/Wineries
We had such a lovely time at the ‘small house’! Jennifer was quick to respond with any questions we had (about the property and the town)! We loved playing yard games and hanging out by the water. The kitchen was stocked with spices and all the things we needed to spend time together cooking. We plan to visit again in the Winter!

Family-Friendly Meets Luxury
we had a nice staycation with the large group. it was peaceful surroundings. our kids had enough games to play. this place is highly recommended

"The Shire" at Hollow View: Crozet Farmhouse
Had a great time with my son and 4 grandsons! Beautiful property in the Blue Ridge Mountains. Megan very accommodating, house worked out great! I’d definitely be a return visitor!

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.

Cozy, relaxing mountain getaway on the golf course
Simply put, this could not have been a better stay. This place had everything we needed and was a short and super easy trip to the slope. The golf course being closed also made it easy for us to get our pups energy out. I highly recommend this spot to anyone coming to stay at the resort. Carol did amazing job communicating and even was willing to work with us on check out time so we could hit the slopes on chekout day. Will definitely be renting again next season if available.

Stylish & Spacious Estate On The Brew Ridge Trail
This house was amazing to stay at! The plan was just to find an Airbnb to stay at while we skied at wintergreen, but we ended up getting rained out and spent almost the whole time in the house. I was so fun the house is full of surprises and fun board games we weren't board for a minute! The beds were super comfortable, and the kitchen has everything you need to cook!

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!

Historic Sherrard House: Walk Downtown
We had a great time staying here. The house is in a great location- a minute or less from downtown Crozet restaurants and shops and very close to many nearby attractions- less than 5 minutes from Pro Re Nata Brewery and less than 10 minutes to Septenary and King Family wineries. The beds were very comfortable and the two full bathrooms were great upstairs. The house was well stocked with spices and a full kitchen. We had a question about turning the heat on and the host responded almost immediately via the app- communication was great!
Quick stats about vacation rentals that are pet-friendly in Wintergreen Resort
Total rentals
220 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
11K reviews
Family-friendly rentals
190 properties are a good fit for families
Rentals with a pool
140 properties have a pool
Rentals with dedicated workspaces
100 properties have a dedicated workspace
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