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

The Inn at Blue Mountain Brewery
The Inn was the best place to prepare for and stay during our daughter’s wedding weekend. We had everything we needed; the house was beautiful and clean; the beds were comfy. We enjoyed relaxing in the hot tub and around the fire after the festivities. We received 20% off the brewery restaurant and the food was extremely tasty. We highly recommend the Inn!

EXIT 107
If, like us, you are looking place to stay where you and your pet can be comfortable, then this place is excellent. The neighborhood is very nice, safe and quiet. The home is spacious and filled with lovely, interesting, creative and thought-provoking things, but not fancy you’d-be-afraid-to-touch things. There are lots of things to do, see, hear, eat and drink quite close by. The host is an amazing person - kind, intelligent, helpful and open. She also has deep roots in Crozet/Charlottesville and can answer any question you might have.

Wilhelm's House- Mountain escape in VA
We visited for the weekend and had a wonderful stay. Peaceful, unique, clean - first words that come to mind when thinking of the Fenton Inn. Recommend making reservations in advance (when needed) for local dining as some of the breweries have limited seating availability due to COVID. Recommend Bold Rock for great food, views, and outdoor dining. We drove to Crabtree Falls for the day, great hike and drive along the Blue Ridge parkway which is just minutes from this location. Excited to see a couple black bear cubs!

Spectacular Mountain View!
My friends and I had a wonderful getaway weekend at Fairview and loved the gorgeous views as well as the history and details of the home. Jennifer was very helpful and proactive in reaching out and very quick to respond to any questions and provided a few local recommendations. Just one thing to note that we hadn't realized at first, is the hot tub is in a shared area with other guests of the neighboring cottage. Which wasn't an issue for us as everyone was respectful of each other and we had it to ourselves when we went for a soak. Overall a wonderful stay and we will hopefully be back in the future!

Crozet Casa w/ Hot-Tub & Firepit in wine country
Stayed here for a bachelorette party. The house was perfect for our group. Bev was so nice and helpful - anything we needed she helped us out! The location is also great if you’re wanting to do a bit of everything - wineries, downtown shopping and dining out, breweries, etc! The yard is amazing and it feels like you’re in the middle of nowhere when you’re outside on the deck. Highly recommend!

Cabin By The Falls
This place is absolutely gorgeous! My friends and I loved the hot tub and pool while listening to the sounds of the creek running close by. Such a cool fun place.

Elegant Cabin with Panoramic View and Private Lake
Great place to get together with friends in a gorgeous getaway cabin. The views and scenery around Crimora is fantastic and the house was exactly as described.

Homestead at HeartRock
My boyfriend and I came out here looking for a place to disconnect and Heartrock was the perfect place! Greg gave us a great hiking recommendation to Fortune’s Cove and Kim was so helpful and responsive. The place was so nice and the scenery was lovely. Bilbo the cat was even more friendly than we imagined and we enjoyed hanging with him. We did prep our own breakfast and dinner before arriving just due to the smaller kitchen but it had everything we needed. We took a stroll around the property and it was lovely. The water pressure here is also great. Overall, we had a great time and would definitely come back.
Family- and pet-friendly home rentals

Stylish Carriage House Suite near Crozet center
Lovely place and very comfortable. Great area to stay in and very walkable

High Street | Walk to Everything Crozet | Pet-Frie
This 3 night trip was part of our 2 week trip visiting family in VA. We chose this house because we have a small dog and thought the yard would be good to have. The house was clean and the kitchen was very well stocked. Amy even left a nice little surprise for us. She answered all our questions and was very helpful. We enjoyed walking to the coffee house and being minutes from our son.

Very Private Cabin - H'Owl at the Moon Farm
Words cannot describe the feeling of pure calm that comes over you when you arrive. This place is truly a treasure hidden in the woods. Once you cross the creek you leave the world and all your cares behind. The host pays attention to all the little details and it shows. We have stayed at quite a few places but this one is on our return list. We look forward to sliding up for a long weekend in the late fall or early winter. (Tip- be sure to spend 15 min reading the welcome package it is time well spent).

#4 Cabin Near Wineries, Breweries, UVA, & Hiking
I cannot count how many times we’ve stayed at Montfair. Heck, my wife and I got married there in July of 23! This is our home away from home which is a short ride from Richmond, yet worlds away. Thank you again for hosting us. We had an excellent end to Spring break at Loblolly. Until next time.

Lotus View Retreat in Yogaville/Chalet
Prishanti was an amazing host! She was extremely friendly and welcoming, and made me feel at home. The place was so beautiful. I wanted to have a weekend to escape and unwind and my goals were accomplished! The view was stunning. It was so quiet and peaceful. There was nearby hiking that I was able to take my dogs. The accommodations were very clean. The best part was just sitting out on the deck as the sun went down drinking a glass of wine with my dogs. The weekend was perfect.

Summer Kayaking free Rockfish! 140 Acres,peaceful!
The cabin is beautiful, clean, and well furnished. Everything matches the description and pictures. John was helpful with finding the place and giving suggestions for activities. Definitely recommend!

Yurt Off Grid Wood heat Getaway 70acre wooded farm
Had a great stay, circumstances of the trip definitely made us more quiet and reserved. would love to stay again on our next trip to va.

Charming Country Cottage
Stayed here for a couple nights for the purpose of celebrating an anniversary and riding bicycles. It’s a great location that’s close enough to Charlottesville but also far enough away that it’s quiet and peaceful. Sidenote, if you’re into Cycling, then it’s a great jump off location.
Family-friendly home rentals with a pool

Walk to Market/Slopes!
As advertised. Good location. Easy check-in

3 Masters Perfect for Multiple Families&NewArcade!
Highly recommend this home for your Wintergreen stay. First, the hosts were extremely proactive in sending detailed information from check-in instructions to suggestions on local activities. The host was responsive within minutes with any questions we had. The house is very well stocked with everything you will need for your stay. The house was very clean, spacious, and comfortable. It was perfect for 3 couples in our party, not many homes have 3 master suites. The house has 2 family rooms which added great additional space. The location is convenient to the Wintergreen lodge, not ski in/ski out but an easy drive down to the resort, seriously just a few minutes. I highly recommend waking up early to enjoy the beautiful sunrise from the big window on the main level, can't beat the views. Everyone in our party was extremely happy with our stay.

Luxury House on Mountain Golf Course: Book Summer
My group and I had a wonderful stay at Gina Marie H's place! So easy to settle in and each description on the photo listing was extremely accurate. The price point is perfect if you have 8 guests in my humble opinion. Some things that really stood out to me was Gina Marie's communication, the fully equipped kitchen and the distance of the house being about 5 minutes main mountain entrance. The road was also less frequently traveled since it was a few miles away off the main mountain road which made it easy to hike and run right out the front door. I could very easily see myself booking this lovely air bnb again!

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!

Gorgeous Rustic Mountain Cabin - Green Oak Cabin
My husband had a great time hosting a Bachelors weekend for one of his good friends. The guys loved the stay at the cabin and loved that it was so close to skiing. They would definitely stay again and maybe next time I can go!

Eagle's Lookout Retreat at Wintergreen Resort, VA
Family friendly location with outstanding views. Very close to slopes.

Wintergreen Retreat
Nathan and the house are truly remarkable, showcasing qualities like amazing, incredible, outstanding, beautiful, kind, generous,sincere and phenominal. I highly recommend them! All praises and blessings! When you book with Nathan, all you need is money and food because they provide everything else you could possibly want and more. Plus, the price is absolutely fair! 🙂

Amazing views! Overlooking Expert Slope
Great place! We love this area of Wintergreen. Willette’s place was clean and had all we needed. Communication was excellent. We would definitely stay again.
Quick stats about vacation rentals that are family-friendly in Wintergreen Resort
Total rentals
520 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
20K reviews
Pet-friendly rentals
190 properties allow pets
Rentals with a pool
310 properties have a pool
Rentals with dedicated workspaces
210 properties have a dedicated workspace
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