Family-friendly holiday 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 favourite
Home in Afton
4.97 out of 5 average rating, 158 reviews

The Inn at Blue Mountain Brewery

JessicaRating, 5 stars3 weeks 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!
Home in Roseland
4.86 out of 5 average rating, 14 reviews

Wilhelm's House- Mountain escape in VA

JaimeRating, 5 stars59 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, 261 reviews

Spectacular Mountain View!

MichelleRating, 5 stars3 weeks ago
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!
Top guest favourite
Home in Crozet
4.97 out of 5 average rating, 201 reviews

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

KristenRating, 5 stars1 month 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 favourite
Cabin in Tyro
4.9 out of 5 average rating, 79 reviews

Cabin By The Falls

CristianeRating, 5 stars6 days ago
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!
Top guest favourite
Flat in Crozet
5 out of 5 average rating, 489 reviews

The Barn at Haden near Wineries and C'ville

KristinRating, 5 stars4 weeks ago
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!
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 favourite
Guest house in Schuyler
4.91 out of 5 average rating, 390 reviews

Homestead at HeartRock

ZoeRating, 5 stars1 month 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
Guest house in Crozet
4.86 out of 5 average rating, 313 reviews

Stylish Carriage House Suite near Crozet center

LaNaeRating, 5 stars2 days ago
I highly recommend this comfortable place. the host is kind and very responsive. I enjoyed my stay and time in Crozet. LaNae
Top guest favourite
Cabin in Schuyler
4.99 out of 5 average rating, 124 reviews

Very Private Cabin - H'Owl at the Moon Farm

MarkRating, 5 stars3 weeks 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).
Top guest favourite
Cabin in Faber
4.97 out of 5 average rating, 135 reviews

Summer Kayaking free Rockfish! 140 Acres,peaceful!

ShanaRating, 5 stars1 week ago
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!
Guest favourite
Apartment in Wintergreen Resort
4.88 out of 5 average rating, 113 reviews

1720 High Ridge at Wintergreen Resort

HuntRating, 5 stars3 months ago
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)
Superhost
Yurt in Afton
4.85 out of 5 average rating, 143 reviews

Yurt Off Grid Wood heat Getaway 70acre wooded farm

JamieRating, 5 stars1 month 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.
Superhost
Cabin in Buckingham
4.89 out of 5 average rating, 197 reviews

Lotus View Retreat in Yogaville / Cabin

Samantha Rating, 5 stars2 months ago
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.
Superhost
Cottage in Arrington
4.92 out of 5 average rating, 118 reviews

Charming 1930’s Soapstone Workers' Bungalow

LawrenRating, 5 stars1 month ago
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!
Guest favourite
Farm stay in Free Union
4.95 out of 5 average rating, 324 reviews

Secluded Private Apartment - Pets Welcome!

DanielleRating, 5 stars3 weeks ago
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

Guest favourite
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 favourite
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!
Top guest favourite
Cabin in Wintergreen Resort
4.88 out of 5 average rating, 128 reviews

The Bear Dance Cabin at Wintergreen Resort

JesseRating, 5 stars4 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 favourite
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 favourite
Cabin in Wintergreen Resort
4.92 out of 5 average rating, 37 reviews

Eagle's Lookout Retreat at Wintergreen Resort, VA

QuincyRating, 5 stars5 months ago
Family friendly location with outstanding views. Very close to slopes.
Top guest favourite
Chalet in Roseland
5 out of 5 average rating, 5 reviews

Wintergreen Retreat

JamesRating, 5 stars1 month 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! 🙂
Apartment in Wintergreen Resort
4.53 out of 5 average rating, 83 reviews

Amazing views! Overlooking Expert Slope

AlexisRating, 5 stars4 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.
Superhost
Cabin in Greenville
4.95 out of 5 average rating, 75 reviews

Cabin on Penmerryl Farm - (2-Night Minimum Stay)

RalitsaRating, 5 stars1 month ago
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

Destinations to explore