Pet-friendly vacation rentals in Wintergreen Resort

Find and book unique pet-friendly homes on Airbnb

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Popular amenities for Wintergreen Resort pet-friendly home rentals

Pet-friendly home rentals with a hot tub

Guest favorite
A secluded cabin is showcased under a night sky, surrounded by fresh snow. Soft light illuminates the front porch, where rocking chairs are positioned. A hot tub is visible nearby, and a car is parked in the snow-covered driveway.
Vacation home in Lovingston
4.97 out of 5 average rating, 188 reviews

Ultimate cabin in the mountains

DerekRating, 5 stars6 days ago
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!
Top guest favorite
A charming white home features dark shutters and a bright yellow front door, framed by colorful foliage. Flags are displayed at the entrance, and a well-maintained lawn enhances the welcoming appearance. The path and landscaping lead to a warm invitation for guests.
Home in Crozet
4.97 out of 5 average rating, 198 reviews

Crozet casa w/ firepit & hot tub in wine country

AlexanderRating, 5 stars1 month 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 Nellysford
4.99 out of 5 average rating, 102 reviews

Mountain Season Lodge

CarolynRating, 5 stars2 months ago
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.
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 stars2 weeks 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
Farm stay in Nellysford
4.91 out of 5 average rating, 574 reviews

The Cottage at Spindle Hill: an Artist’s Farm

WynneRating, 5 stars6 days ago
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.
Guest favorite
A cabin is set amidst colorful autumn foliage, showcasing a covered front porch with red rocking chairs. Steps lead up to the entryway, and the surrounding landscape features fallen leaves and natural terrain, presenting a serene and rustic charm.
Cabin in Wintergreen Resort
4.95 out of 5 average rating, 107 reviews

Hot Tub DogsOK Grill Fireplace Pac Man Pool Tennis

JonathanRating, 5 stars1 week ago
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!
Guest favorite
Chalet in Vesuvius
4.94 out of 5 average rating, 219 reviews

Luxury Mountain Lodge w/ Hot Tub & Stunning Views!

KijonaRating, 5 stars3 weeks ago
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!
Superhost
Home in Afton
4.91 out of 5 average rating, 101 reviews

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

KristinaRating, 5 stars2 weeks ago
Very happy with our stay. Beautiful mountain drive.

Pet-friendly home rentals with a pool

Top guest favorite
A bright living area features a teal couch adorned with a yellow cushion, complemented by a soft throw blanket. A coffee table sits in front, while a gray armchair is positioned nearby. Natural light pours in from the sliding glass doors, enhancing the space's inviting ambiance.
Condo 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 favorite
A charming farmhouse with a white exterior and green shutters is surrounded by lush gardens. A small round table with white chairs sits among blooming azaleas. Two large trees provide shade in the front yard, complementing the inviting porch.
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.
Guest favorite
The cabin features a warm wooden exterior with a red metal roof, set against a backdrop of lush greenery. A spacious front porch is presented, supported by wooden columns and adorned by wooden railing, inviting guests to enjoy the surrounding nature.
Cabin in Wintergreen Resort
4.88 out of 5 average rating, 128 reviews

The Bear Dance Cabin at Wintergreen Resort

JesseRating, 5 stars2 months ago
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!
Guest favorite
A charming two-story condo is surrounded by trees and seasonal foliage. A wooden deck is visible at the entrance, offering an inviting access point. The natural setting provides a tranquil backdrop, with a mix of bare branches and remaining leaves from the autumn season.
Home in Wintergreen Resort
4.96 out of 5 average rating, 107 reviews

Bear's Mountain Escape

HeatherRating, 5 stars2 weeks ago
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!
Guest favorite
A cozy living area features natural stone accents around a wood-burning fireplace. A small dining table with two chairs is positioned near large windows, allowing ample natural light. Green accent walls enhance the inviting atmosphere, while a comfortable seating area is visible nearby.
Condo in Wintergreen Resort
4.9 out of 5 average rating, 167 reviews

Tips Up: Cozy Slopeside Retreat w/ Fireplace

DennisRating, 5 stars1 week 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 favorite
A bright and airy living area is highlighted by large windows offering mountain views. A casual seating arrangement features a light-colored sofa and a wooden dining table surrounded by black chairs. Sliding glass doors provide access to an outdoor deck.
Apartment in Rockfish
4.98 out of 5 average rating, 189 reviews

Blue Ridge Bliss - For family & friends to enjoy!

AngelaRating, 5 stars2 weeks ago
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.
Guest favorite
A balcony view captures rolling green hills beneath a layer of clouds, with distant mountain peaks rising above. A wrought iron dining set is present on the balcony, providing a serene space for enjoying the landscape.
Condo 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!
Top guest favorite
The entrance to the condo is framed by greenery and features double doors. A small patio with seating is visible, surrounded by fallen leaves, creating a natural and inviting setting.
Condo 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.

Pet-friendly house rentals

Guest favorite
The exterior of the house features a covered porch with two chairs, adorned with decorative cushions. Potted plants are placed on either side of the porch steps. A flag waves gently in the breeze, with mountains visible in the background under a partly cloudy sky.
Home in Nellysford
4.97 out of 5 average rating, 136 reviews

“Small" House/Peaceful/Breweries/Hikes/Wineries

BrittanyRating, 5 stars1 week ago
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!
Guest favorite
Home in Roseland
4.95 out of 5 average rating, 41 reviews

Family-Friendly Meets Luxury

ShusheelRating, 5 stars6 days ago
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
Guest favorite
Home in Crozet
4.97 out of 5 average rating, 106 reviews

"The Shire" at Hollow View: Crozet Farmhouse

DougRating, 5 stars5 days ago
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!
Guest favorite
A spacious house is seen set back among tall trees adorned with autumn foliage, creating a natural canopy. A paved driveway leads to the front of the home, which features a covered porch and large windows, inviting plenty of natural light.
Home in Afton
4.96 out of 5 average rating, 241 reviews

CritzerHouse - on 151- Walk to the Brewery!

KarenRating, 5 stars2 weeks 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.
Top guest favorite
A charming mountain house showcases a dark wooden exterior surrounded by autumn foliage. Large windows are framed by trees, and a welcoming front porch is visible, adding to the cozy appearance of the property.
Home in Wintergreen Resort
4.99 out of 5 average rating, 101 reviews

Cozy, relaxing mountain getaway on the golf course

CarterRating, 5 stars2 months ago
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.
Guest favorite
A bright blue-green bedroom features a hand-carved wooden bed adorned with floral-patterned bedding. A simple desk and chair sit adjacent to a large decorative cabinet, while glass doors open to a vibrant, colorful outdoor seating area.
Home in Afton
4.97 out of 5 average rating, 349 reviews

Stylish & Spacious Estate On The Brew Ridge Trail

ErikaRating, 5 stars2 months ago
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!
Guest favorite
A welcoming porch is shown, featuring two white rocking chairs positioned beside a small round table. The wooden floor is painted gray, and a bright yellow exterior wall adds a cheerful touch. A window is visible, allowing natural light to fill the space.
Home in Staunton
4.91 out of 5 average rating, 139 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!
Superhost
A sizable outdoor deck is framed by wooden beams, offering a lounge area with two slatted chairs and a fire pit at the center. A potted plant adds a touch of greenery, while the background features large glass doors leading to the house.
Home in Crozet
4.86 out of 5 average rating, 77 reviews

Historic Sherrard House: Walk Downtown

SarahRating, 5 stars6 months ago
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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