
Family-friendly holiday 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!

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!
Wow! What an amazing place! We had so much fun! There is plenty of space inside—7 bedrooms and 6 baths—with plenty of places to congregate. Front porch, back porch, fire pit and other outside seating areas are wonderful! The huge house was clean and inviting. It is a wonderful escape!

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
My family and I were looking for a place away from the fast pace and noise of our day to day routine and this place did not disappoint. With the lovely river running right out front, a beautiful waterfall trail literally next door, the fun pool, and relaxing jacuzzi we never had a dull moment. The place was a great size where we can enjoy family time but also have our personal space to unwind. If you are thinking of booking, don’t think just do it because it was truly amazing!

The Barn at Haden near Wineries and C'ville
Beautifully decorated and extremely clean! Had everything we could have possibly wanted and the location was perfect for visiting wineries and breweries! We would definitely stay here again on our next visit to the area!

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
I highly recommend this comfortable place. the host is kind and very responsive. I enjoyed my stay and time in Crozet. LaNae

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).

Summer Kayaking free Rockfish! 140 Acres,peaceful!
We stayed here for a wedding in Charlottesville and, while the cabin was a bit out of the way from where most guests were staying in town, it ended up being the best decision we made. Our group was too large for hotel rooms, and this cabin gave us the perfect place to spread out and relax. We honestly wished we had more time to enjoy the space itself—it's ideal for a peaceful getaway weekend. Unfortunately, wedding events kept us running around, but we could easily see ourselves coming back just to unwind and take it all in. The property offers plenty to do, and the atmosphere is cozy and inviting. A couple of small suggestions that would’ve helped us (specifically as guests getting ready for a wedding): a full-length mirror in the downstairs bathroom and some brighter lighting in the bathrooms for hair and makeup. That said, these things wouldn’t be an issue for a regular weekend trip. Overall, a charming cabin that we hope to return to when we can truly enjoy it!

1720 High Ridge at Wintergreen Resort
Beautiful location with the daily sunrise over the blue ridge mountains is captivating. Kimberly who manages the property is the provides the best customer service I've ever had at Air B&B . (Got well over 100 nights in withAirB&B)

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.

Lotus View Retreat in Yogaville / Cabin
We loved the large deck with incredible views! There is another property very close to this one so wasn’t as secluded as we had hoped but overall we loved our stay here. Go check out Eagle Zen Winery if you have the chance.

Charming 1930’s Soapstone Workers' Bungalow
We came into town for a graduation at Liberty University. The house is on a dirt road well off the beaten path (which I love). It was a very beautiful area, very peaceful even with neighbors nearby. We were delighted to find that the host gifted us a 6 pack of Bold Rock Cider, which oddly enough is my favorite cider (I’m gluten free). Everything was clean, with the exception of the inside of the fridge. My kids played their hearts out running around the yard, swinging, roasting marshmallows. My only complaint is the tiny showers, but I’m claustrophobic 😂😂 otherwise, we had a wonderful stay and would stay again!

Secluded Private Apartment - Pets Welcome!
Beautiful and peaceful. Enjoyed the lush green surroundings and watching the bunnies and deer. Felt secluded but was well marked so we had no problems finding it. The place had everything we needed for a short stay.
Family-friendly home rentals with a pool

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.

Cabin on Penmerryl Farm - (2-Night Minimum Stay)
My family and I truly enjoyed our stay. My husband took our kids (ages 10 and 7) fishing on the property, which they absolutely loved. We spent time swimming in the pool and hiking the beautiful surroundings. We also visited the nearby Virginia Safari Park and Natural Bridge Park—both were wonderful day trips. The host was fantastic, and the property was peaceful and relaxing. We’d love to come back!
Quick stats about holiday rentals that are family-friendly in Wintergreen Resort
Total rentals
520 properties
Nightly prices starting at
₹6,060 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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