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Family-friendly vacation rentals in Wintergreen Resort

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Wintergreen Resort family-friendly rentals

Family-friendly home rentals with a hot tub

Top guest favorite
Home in Afton
4.97 out of 5 average rating, 158 reviews

The Inn at Blue Mountain Brewery

JessicaRating, 5 stars6 days ago
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!
An array of colorful origami cranes is presented in a decorative bowl, featuring vibrant colors such as red, blue, and orange, among others. The cranes are made from various types of paper, showcasing intricate folding techniques, adding a unique decorative touch to the space.
Home in Crozet

EXIT 107

NancyRating, 5 stars68 months ago
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.
A charming exterior showcases a Bavarian-style building with intricate wooden details and classic architecture. Multiple windows with decorative planters are visible, reflecting the surrounding landscape. The soft hues of the exterior walls complement the natural greenery, creating an inviting atmosphere.
Home in Roseland
4.86 out of 5 average rating, 14 reviews

Wilhelm's House- Mountain escape in VA

JaimeRating, 5 stars58 months ago
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!
Home in Amherst
4.79 out of 5 average rating, 260 reviews

Spectacular Mountain View!

Marissa A.J.Rating, 5 stars3 months ago
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!
Top guest favorite
A bright dining area features a colorful tablecloth over a large dining table surrounded by black-and-white patterned chairs. Natural light floods in through large windows, highlighting art on the walls. An outdoor grill is visible through the glass doors, enhancing the inviting space.
Home in Crozet
4.97 out of 5 average rating, 200 reviews

Crozet Casa w/ Hot-Tub & Firepit in wine country

KristenRating, 5 stars3 weeks ago
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!
Top guest favorite
The cabin is situated among lush greenery, seen from the flowing Tye River. Water cascades over rocks in the foreground, while the wooden structure is nestled in the trees. A spacious deck extends from the cabin, blending seamlessly with the natural landscape.
Cabin in Tyro
4.9 out of 5 average rating, 78 reviews

Cabin By The Falls

MeaghanRating, 5 stars4 weeks ago
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.
The custom log home features a spacious balcony with large windows, allowing for abundant natural light. Surrounding the house are well-placed boulders and a stone fire pit, providing an inviting outdoor gathering space amid lush greenery.
Cabin in Crimora
5 out of 5 average rating, 5 reviews

Elegant Cabin with Panoramic View and Private Lake

FrancisRating, 5 stars77 months ago
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.
Guest favorite
A natural stone patio is surrounded by trees, featuring a vintage cast iron tub as a focal point. The space is complemented by two planters filled with colorful flowers and an adjacent wooden table, enhancing the outdoor setting.
Guesthouse in Schuyler
4.91 out of 5 average rating, 390 reviews

Homestead at HeartRock

ZoeRating, 5 stars4 weeks ago
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

Superhost
A functional kitchen area features a wooden island with two black stools. Natural light fills the space, highlighting the reclaimed barn wood accents and white cabinetry. A cozy seating area is visible nearby, with a small coffee table and colorful rug adding warmth.
Guesthouse in Crozet
4.86 out of 5 average rating, 311 reviews

Stylish Carriage House Suite near Crozet center

MartinRating, 5 stars1 week ago
Lovely place and very comfortable. Great area to stay in and very walkable
Top guest favorite
A charming green cottage features a covered front porch with seating, inviting visitors to enjoy outdoor moments. The well-maintained yard showcases a mix of grass and stone pathways, with large windows allowing natural light to enhance the inviting exterior.
Cottage in Crozet
4.98 out of 5 average rating, 252 reviews

High Street | Walk to Everything Crozet | Pet-Frie

JanetRating, 5 stars4 days ago
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.
Top guest favorite
The rustic log cabin is framed by a lush green landscape. A covered front porch extends across the front, featuring a stack of firewood neatly arranged beside it. Large windows allow natural light to illuminate the interior, while a charming arched window adds character to the upper level.
Cabin in Schuyler
4.99 out of 5 average rating, 124 reviews

Very Private Cabin - H'Owl at the Moon Farm

MarkRating, 5 stars5 days ago
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).
Superhost
A rustic cabin constructed of timber sits amidst a wooded area, showcasing a wraparound porch with steps leading up. Large windows provide glimpses of the surrounding trees, while gravel paths lead to the entrance, enhancing the natural setting.
Cabin in Crozet
4.86 out of 5 average rating, 101 reviews

#4 Cabin Near Wineries, Breweries, UVA, & Hiking

JasonRating, 5 stars1 month ago
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.
Superhost
Lush greenery surrounds the James River, reflecting the vibrant landscape. The view captures gentle slopes and a serene water surface, enhancing the peaceful ambiance. In the distance, distinctive white domes can be seen peeking through the foliage, contributing to the picturesque rural setting.
Cabin in Buckingham
4.93 out of 5 average rating, 183 reviews

Lotus View Retreat in Yogaville/Chalet

ChrisRating, 5 stars1 month ago
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.
Top guest favorite
A serene river flows gently through a wooded area, with sparkling waters reflecting sunlight. Leafless trees line the riverbank, and a backdrop of a forested hillside adds depth to the tranquil scene.
Cabin in Faber
4.97 out of 5 average rating, 133 reviews

Summer Kayaking free Rockfish! 140 Acres,peaceful!

JamilaRating, 5 stars2 weeks ago
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!
Superhost
The styled yome features a green roof and a circular structure, surrounded by trees. A wooden deck extends from the entrance, which includes a window. A fire pit with stones and a single grey chair are positioned in the foreground, set against a backdrop of autumn foliage.
Yurt in Afton
4.85 out of 5 average rating, 143 reviews

Yurt Off Grid Wood heat Getaway 70acre wooded farm

JamieRating, 5 stars4 weeks ago
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.
Guest favorite
A bright sleeping area is defined by a spacious bed with striped linens and a cozy throw. Two windows allow natural light, illuminating the wood flooring. A dresser and a rocking chair are positioned nearby, complementing a small decorative rug that adds warmth.
Cottage in Free Union
4.9 out of 5 average rating, 194 reviews

Charming Country Cottage

LucasRating, 5 stars4 weeks ago
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

Guest favorite
An aerial view of a living and dining space reveals comfortable seating arranged around a wooden coffee table. A dining table is flanked by four chairs, positioned next to large windows that overlook a wooded area. Soft lighting adds to the cozy atmosphere.
Apartment in Wintergreen Resort
4.85 out of 5 average rating, 123 reviews

Walk to Market/Slopes!

JosephRating, 5 stars3 months ago
As advertised. Good location. Easy check-in
Guest favorite
A spacious living room is highlighted by a stone fireplace, surrounded by wooden beams and high ceilings. Comfortable sofas are arranged around a central coffee table, with a view of large windows that reveal the natural surroundings. A TV setup and bookshelves add convenience.
Chalet in Wintergreen Resort
4.7 out of 5 average rating, 37 reviews

3 Masters Perfect for Multiple Families&NewArcade!

MirraRating, 5 stars3 months ago
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.
Top guest favorite
The exterior of the house features a modern design with a combination of gray siding and a shingled roof. Surrounded by trees, the entryway is framed by steps leading to the front door, with a spacious driveway visible in the foreground.
Home in Wintergreen Resort
4.89 out of 5 average rating, 55 reviews

Luxury House on Mountain Golf Course: Book Summer

AnastasiaRating, 5 stars3 months ago
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!
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 stars3 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 vibrant sunset paints the sky in hues of orange, pink, and purple, with wispy clouds adding texture. The silhouette of nearby mountains is visible beneath the colorful display, framed by the lush foliage of a tree in the foreground.
Cabin in Wintergreen Resort
4.8 out of 5 average rating, 102 reviews

Gorgeous Rustic Mountain Cabin - Green Oak Cabin

LoreleiRating, 5 stars16 months ago
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!
Guest favorite
A deck is shown with black wrought iron furniture, including a small table and chairs. Fallen leaves are scattered on the wooden surface. Surrounding trees display autumn foliage, revealing distant mountain views under a cloudy sky.
Cabin in Wintergreen Resort
4.92 out of 5 average rating, 37 reviews

Eagle's Lookout Retreat at Wintergreen Resort, VA

QuincyRating, 5 stars4 months ago
Family friendly location with outstanding views. Very close to slopes.
Top guest favorite
An inviting living area features large windows that allow natural light to flood the space. A mix of comfortable seating includes a light-colored sofa and dark armchairs, with a decorative area rug and a hardwood floor enhancing the room's charm.
Chalet in Roseland
5 out of 5 average rating, 5 reviews

Wintergreen Retreat

JamesRating, 5 stars3 weeks ago
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! 🙂
A spacious balcony offers outdoor seating with a glass-top table and four metal chairs. Expansive mountain views extend beyond the boundary, showcasing rolling hills under a clear blue sky.
Condo in Wintergreen Resort
4.53 out of 5 average rating, 83 reviews

Amazing views! Overlooking Expert Slope

AlexisRating, 5 stars3 months ago
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

Destinations to explore