Pet-friendly vacation rentals in Wintergreen Resort

Find and book unique pet-friendly homes on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for Wintergreen Resort pet-friendly home rentals

Pet-friendly house rentals

Guest favourite
Home in Nellysford
4.97 out of 5 average rating, 136 reviews

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

BrittanyRating, 5 stars2 weeks 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 favourite
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 favourite
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.
Guest favourite
Home in Wintergreen Resort
4.96 out of 5 average rating, 108 reviews

Bear's Mountain Escape

CherylRating, 5 stars2 weeks ago
Having the lovely house in this location enabled our family to "meet in the middle" and enjoy Easter! It is a lovely place and felt like home! We were grateful for all the little extra touches! The lookout and hiking trail were both beautiful. The Market was a short walk from the house and the Discovery center was great for our granddaughter. Everyone we met in the area was friendly, including the firefighters who took time out from training to show their truck to the children! Thank you Elizabeth! We highly recommend this place!
Top guest favourite
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 favourite
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!
Superhost
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!
Superhost
Home in Afton
4.88 out of 5 average rating, 80 reviews

Sweet Afton | House in Heart of Wine Country

MiekeRating, 5 stars1 week ago
The house is very welcoming, the yard beautiful and private. There are some sounds of traffic and neighbors, which was a bit of a surprise for us. We had gotten a different impression from the description and pictures. But all in all this was a peaceful and pretty ideal place. Only other comment: it would be helpful to have some instructions for the TV etc. We could not find any. Nor were there helpful suggestions for things to do or where to eat. Overall a great place

Pet-friendly home rentals with a pool

Top guest favourite
Condo in Wintergreen Resort
4.97 out of 5 average rating, 127 reviews

Mtn/Firework Views from Private Deck ~ King Suite

AlyssaRating, 5 stars4 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
Home in Roseland
4.95 out of 5 average rating, 41 reviews

Family-Friendly Meets Luxury

ShusheelRating, 5 stars1 week 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 favourite
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!
Superhost
Cabin in Wintergreen Resort
4.87 out of 5 average rating, 79 reviews

Dog Friendly - Backs to Golf - Spacious Deck

JillRating, 5 stars2 months ago
Pip's place is close enough to all the features that Wintergreen Resort offers to make them easily accessible, but far enough away to give you space and quiet. It backs up to the golf course so the back has a lovely setting. We were especially grateful that the place is dog friendly. We would totally recommend this spot and would stay again in the future.
Top guest favourite
Apartment in Rockfish
4.98 out of 5 average rating, 190 reviews

Blue Ridge Bliss - For family & friends to enjoy!

KimRating, 5 stars2 weeks ago
Wonderful stay ! This condo is so adorable ! As everyone says , the views are better than the pictures ! I love the way the condo is set up . It’s updated and cozy and you can tell they put a lot into the look of the place. The outdoor space was so enjoyable . Thank you for a wonderful time !
Guest favourite
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 favourite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 246 reviews

Cozy, clean, quiet mountain condo- King bed

ChristieRating, 5 stars2 weeks 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.
Top guest favourite
Apartment in Lovingston
5 out of 5 average rating, 41 reviews

Loft on the Knoll -Private pool now open

ThomasRating, 5 stars2 weeks ago
My Fiancé and I loved this for a romantic weekend getaway. A quiet and beautiful setup with plenty of outdoor activities around. A very comforting stay and definitely would book again.

Private, pet-friendly home rentals

Top guest favourite
Yurt in Amherst
4.93 out of 5 average rating, 213 reviews

Glamp in a yurt- camping but with style & comfort.

BetsyRating, 5 stars4 months ago
Fran was an exceptional host, and the yurt was such a fun way to ring in the New Year. I won't mince words: it was chilly, but the buddy heater was a welcome amenity, and the bed was beyond comfy and piled high with blankets. The bathhouse 250 steps away was terrific, but by far and away my favorite perk was the en suite--the composting toilet around the corner on the deck, something I didn't know about until I arrived! Fran thinks of everything, and, given I was starving on arrival, the freshly baked bread was such a welcome treat. If you're a beer drinker, don't miss Blue Mountain Barrel House & Smokin' Barrel Restaurant. Thank you, Fran!
Top guest favourite
Home in Charlottesville
5 out of 5 average rating, 23 reviews

Casa Crozet

MattRating, 5 stars1 week ago
Host very responsive given our short notice to book. House is in a great location for a winery weekend. Spacious home with great furnishings and comfy beds. Would stay here again. A extra coffee mug or two to add to the cupboards would be a plus 😜. Overall satisfied with our experience.
Superhost
Farm stay in Amherst
4.85 out of 5 average rating, 47 reviews

Private, Breathtaking Mountain Views, dogs welcome

JohnRating, 5 stars2 weeks ago
Visited from DC, looking for a weekend getaway. We got what we were looking for. The expectations were well managed by the photos and description. The space was really comfortable—all kitchen necessities available (we made breakfast both mornings), living room with streaming capabilities, bathroom with shower and tub, and one bedroom (cozy). It felt like one of those Safari hotels where the animals are right outside your window, except here it was cows and their calves—which was cool for us not being around farms very often. Surprisingly, there was no smell inside or outside on the property with all the animals. There were flies, but we kept the doors closed and there were no issues with bugs. Mattress was pretty firm. Plenty of seating outside (benches, rocking chairs, tall boys). Pasture and view of mountains were beautiful. The host was responsive and friendly. Loved the stay here and already talking about visiting again!
Top guest favourite
Cabin in Schuyler
4.99 out of 5 average rating, 122 reviews

Very Private Cabin - H'Owl at the Moon Farm

MichaelRating, 5 stars2 weeks ago
We loved our stay at this cabin! It offered total privacy, making it feel like our own little hideaway in nature. The surroundings were stunning—peaceful woods, fresh air, and gorgeous views all around. Inside, the cabin was cozy and thoughtfully furnished for comfort. We enjoyed walking down to see the waterfall on the lower field. The a/c was refreshing for what turned out to be a summer-like Easter. A perfect escape for a long weekend!
Guest favourite
Cabin in Wintergreen Resort
4.97 out of 5 average rating, 75 reviews

On The Rocks

RavenRating, 5 stars3 months ago
Alex and Elise are such awesome hosts! This was our 3rd time staying in their beautiful home and we have never had any issues. The house is beautiful and always in such pristine condition. The views are amazing. We always feel so welcome, even before we make the trip! Highly recommend!
Top guest favourite
Cabin in Montebello
5 out of 5 average rating, 25 reviews

Blue Ridge Cabin 5

KatieRating, 5 stars4 months ago
Spent New Year's with my husband and two Yorkies nestled deep in the woods, and it was everything I hoped for—and more! The property is surrounded by towering trees, offering a sense of tranquility and seclusion that's hard to come by. The bed deserves a special mention— it was the most comfortable bed I’ve ever slept in! We spent all three days hiking some of the best trails and relaxed comfortably watching TV in the evenings with a nice glass of Malbec. If you're looking for a peaceful retreat where you can reconnect with nature without sacrificing comfort, this Airbnb is the perfect choice. I’ll definitely be returning! Thank you Jerry and Chris.
Guest favourite
Farm stay in Free Union
4.95 out of 5 average rating, 321 reviews

Secluded Private Apartment - Pets Welcome!

KatelinRating, 5 stars3 weeks ago
Jonathan and Sibylle were great hosts! They were so attentive to anything we may need. They have a beautiful property making for a perfect weekend getaway! The space was very well kept. Everything was so appreciated!
Guest favourite
Condo in Wintergreen Resort
4.92 out of 5 average rating, 60 reviews

Vineyards, Views & Brews with 2 Floors

GinaRating, 5 stars2 months ago
Owners great to work with and very responsive. Place is cozy with beautiful views, ideally located within Wintergreen. Highly recommend!

Quick stats about vacation rentals that are pet-friendly in Wintergreen Resort

  • Total rentals

    220 properties

  • Nightly prices starting at

    $96 CAD 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

Destinations to explore