Kid-friendly holiday rentals in Wintergreen Resort

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for Wintergreen Resort kid-friendly rentals

Child-friendly house rentals

Guest favourite
Home in Wintergreen Resort
4.88 out of 5 average rating, 135 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

KatieRating, 5 stars1 month ago
We had the absolute best time staying here. We had two families staying together, 10 total. With more than enough space! The location was perfect. The space was clean and cozy. We had the best time and made some amazing memories with our friends. Also we slept at night on the third floor with a window opened and it was so quiet outside! Thank you for opening your home to us!
Guest favourite
Home in Nellysford
4.97 out of 5 average rating, 134 reviews

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

LynetteRating, 5 stars1 month ago
We had a lovely stay in "The Small House" over President's day weekend. The house was spacious enough for 5 guests and our dog. Loved that it was decorated for Valentine's day! The house was well situated in the valley so there was easy access to Wintergreen, hiking trails and all the breweries and wineries!!
Top Guest favourite
Home in Lovingston
4.93 out of 5 average rating, 150 reviews

Three Springs with EV charging station

HeleneRating, 5 stars1 week ago
very nice house in an amazing place. We were with friends for a wkd and it was the perfect aera. I recommend this house. Clear communication with Deborah.
Top Guest favourite
Home in Crozet
4.97 out of 5 average rating, 197 reviews

Crozet casa w/ firepit & hot tub in wine country

MeganRating, 5 stars2 weeks ago
A Perfect Stay – Comfortable, Charming, and Convenient! We had a wonderful stay at Bevin’s Airbnb! From the moment we arrived, we felt right at home thanks to Bevin's warm hospitality and thoughtful touches throughout the space. The beds were incredibly comfortable, making it easy to relax and get a great night's sleep after a day of exploring. One highlight was definitely the hot tub—such a perfect way to unwind! The decor is vibrant, colorful, and so tasteful. The whole place felt cozy and inviting, yet stylish. It truly enhanced the overall experience and made the space feel like a home away from home. Bevin is an exceptional host. She was incredibly responsive, always checking in to make sure we had everything we needed; her kindness made the experience even more special. The location is perfect— close to downtown Charlottesville and the nearby wineries! making it an ideal base for anyone looking to enjoy both the local culture and the beautiful countryside. HIGHLY RECOMMEND!
Guest favourite
Home in Crozet
4.97 out of 5 average rating, 105 reviews

"The Shire" at Hollow View: Crozet Farmhouse

JodiRating, 5 stars4 weeks ago
Great farm house and wonderful experience. Was so nice to be able ti being the dogs. They loved the field.
Guest favourite
Home in Nellysford
4.99 out of 5 average rating, 102 reviews

Mountain Season Lodge

CarolynRating, 5 stars1 month ago
My family had a wonderful time staying at this beautiful house. It was a perfect fit for us. There was plenty of room for everyone and we had a great time playing cards in the evening and watching movies. My 4 and 2 year old grandsons looked forward to going to bed at night so they could take a bath in the jacuzzi tub. The house had everything you could possibly want. The hot tub was a hit with my grown children. We look forward to returning in the future.
Guest favourite
Home in Afton
4.96 out of 5 average rating, 238 reviews

CritzerHouse - on 151- Walk to the Brewery!

BeckyRating, 5 stars2 weeks ago
First ever girls weekend for 4 lifelong friends went GREAT! The location of the home was perfect - so close to many restaurants, wineries & breweries. We also checked out the antique & craft shops! Michele was as quick as humanly possible to respond to & remedy an issue with the front door lock. A wonderful place to stay in Afton (Rt 151)! Thanks!
Guest favourite
Home in Wintergreen Resort
4.95 out of 5 average rating, 220 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

CarlaRating, 5 stars1 month ago
Family of ten weekend trip to Saltbox was wonderful. Loved the space - 3 levels, beautiful views from the large windows, quiet and peaceful neighborhood and ample kitchen amenities. We cooked in the home for all meals and used the outdoor electric grill as well. Host was one of the most communicative of any Airbnb that I've stayed in - felt good to get info and know if you needed anything you wouldn't have to wait long for a response. The value of being within Wintergreen Resort in a clean and spacious home for the cost paid was outstanding.

Kid-Friendly apartment rentals

Guest favourite
Apartment in Lovingston
4.89 out of 5 average rating, 136 reviews

Lovingston Get-Away Lovingston, VA

JacquelynRating, 5 stars1 month ago
Great cozy spot in Lovingston! Ed was a wonderful host, very responsive and helpful. Despite all the rain we were able to have a lovely weekend getaway. Wineries and restaurant options close by.
Top Guest favourite
Apartment in Staunton
5 out of 5 average rating, 118 reviews

Queen City Hideaway

ErinRating, 5 stars2 weeks ago
I was after a peaceful and comfortable place that I could enjoy both inside and outside. This was the perfect location! Inside was cozy, well equipped, and felt safe. Outside was beautiful and comfortable. Truly met every one of my expectations.
Guest favourite
Apartment in Wintergreen Resort
4.92 out of 5 average rating, 132 reviews

Stone Ridge at Wintergreen

AmyRating, 5 stars1 month ago
We loved our stay! It was a great location with a nice view, and we felt right at home in the space. We would definitely stay here again!
Guest favourite
Apartment in Staunton
4.93 out of 5 average rating, 556 reviews

Lewis Creek Loft

JessicaRating, 5 stars6 days ago
We loved our stay! Very comfortable and lovely touches. Was very close to wonderful restaurants and breweries. We will definitely be back!
Top Guest favourite
Apartment in Staunton
4.94 out of 5 average rating, 163 reviews

Traveler’s Escape-1 bedroom. Walk to downtown!

BarbaraRating, 5 stars1 week ago
The apartment was spacious and nicely appointed with everything needed for a short getaway. Susan communicated timely information and instructions for checkin and checkout. A very pleasant place to stay when visiting Staunton.
Top Guest favourite
Apartment in Staunton
5 out of 5 average rating, 268 reviews

The Downtown Corner Place - Location and Luxury

MarkRating, 5 stars1 week ago
We stayed 4 nights and our visit to Staunton was fantastic. Martha's place was even better that we could have imagined. Very comfortable furniture, especially the king sized bed and beautiful decor throughout the apartment. A wonderful home base from which to explore Staunton and surrounding sites and relax after a long day. We intend to return this fall.
Top Guest favourite
Apartment in Staunton
4.98 out of 5 average rating, 327 reviews

The Bons Amis Suite: Walk Downtown!

SophiaRating, 5 stars6 days ago
Just a beautiful apartment! The bed was very comfortable and the place was very clean. The well-equipped kitchen was great for cooking. I also love the location. It is close coffee shops, restaurant and the theater.we will be back!
Guest favourite
Apartment in Afton
4.97 out of 5 average rating, 174 reviews

Mountain View Getaway

ElizabethRating, 5 stars4 months ago
We enjoyed our weekend stay at the property! The view is absolutely stunning. The goats were friendly and so cute. Michelle was responsive and left clear instructions as well as some local recommendations. The property is ~1 mile down any paved road and can be a bit difficult to find at night. However, it added to the country feel! We had absolutely no issues during our stay and would return in the future!

Child-Friendly Holiday Condos

Guest favourite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 213 reviews

The Modern Mountain Condo

JustinRating, 5 stars1 week ago
Perfect for our quick trip to Crozet & Wintergreen Resort. Wonderful location, close to Gas Station/Convenience Store, Wintergreen Lobby, and Slopes. Everything was exactly as expected. Comfortable bed and easy access to streaming services and Wifi. Will definitely consider staying here again for future trips to the area. Thanks so much!
Top Guest favourite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 128 reviews

All-Season 2bd/2ba next to Spa view of Golf Course

WhitneyRating, 5 stars1 month ago
We had a wonderful stay at this Wintergreen condo. Location was great and we loved we could bring our dog. The place was very clean and had all necessities we needed. It was very cozy and we felt right at home. Kim was very responsive and friendly to deal with. All the instructions were clear and easy. We would definitely recommend and would come back!
Guest favourite
Condo in Wintergreen Resort
4.88 out of 5 average rating, 113 reviews

1720 High Ridge at Wintergreen Resort

HuntRating, 5 stars1 month 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)
Top Guest favourite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 204 reviews

New Construction! 1 Bed/2 Bath, pet friendly

AmandaRating, 5 stars4 weeks ago
Lisa's condo was fabulous! It was decorated beautifully and in a very peaceful location. It was great not having to walk up and down multiple flights of stairs. If you need anything, she is quick to answer. It was the cleanest dog friendly Airbnb that we have ever stayed in!! We have a hypoallergenic dog so I appreciated not being covered in dog hair. We will definitely be staying again in the future! Thank you, Lisa!
Guest favourite
Condo in Wintergreen Resort
4.91 out of 5 average rating, 215 reviews

Light Filled Awe-Inspiring Views from Every Window

MattRating, 5 stars1 month ago
Great place. Beautiful view. Everything you’d need.
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 stars4 weeks 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, 245 reviews

Cozy, clean, quiet mountain condo- King bed

MichaelRating, 5 stars4 weeks ago
Ritta’s place was incredibly cozy and comfortable! Fast internet was a great plus. Would absolutely recommend.
Top Guest favourite
Condo in Wintergreen Resort
4.98 out of 5 average rating, 130 reviews

2-min drive from hiking/resort, stairs-free

SavannaRating, 5 stars1 week ago
Mary was a great host. Very detailed with check in and check out. Just right up the mountain from a couple of breweries.

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