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 stars2 months 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, 136 reviews

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

BrittanyRating, 5 stars2 weeks ago
We had such a lovely time at the ‘small house’! Jennifer was quick to respond with any questions we had (about the property and the town)! We loved playing yard games and hanging out by the water. The kitchen was stocked with spices and all the things we needed to spend time together cooking. We plan to visit again in the Winter!
Guest favourite
Home in Lovingston
4.93 out of 5 average rating, 150 reviews

Three Springs with EV charging station

HeleneRating, 5 stars1 month 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, 198 reviews

Crozet casa w/ firepit & hot tub in wine country

AlexanderRating, 5 stars1 month ago
Not only was the house and property fantastic, but the responsiveness and support from the hosts before/during/after was top notch. Everything went smooth with the entire stay, and we'd highly recommend.
Guest favourite
Home in Crozet
4.97 out of 5 average rating, 106 reviews

"The Shire" at Hollow View: Crozet Farmhouse

DougRating, 5 stars1 week ago
Had a great time with my son and 4 grandsons! Beautiful property in the Blue Ridge Mountains. Megan very accommodating, house worked out great! I’d definitely be a return visitor!
Guest favourite
Home in Nellysford
4.99 out of 5 average rating, 102 reviews

Mountain Season Lodge

CarolynRating, 5 stars2 months 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, 241 reviews

CritzerHouse - on 151- Walk to the Brewery!

KarenRating, 5 stars3 weeks ago
We had a great stay at the Critzer House. It was just as described and perfect for our two families of four. Plenty of room for all of us to hang out together or retreat to separate spaces for some quiet time. The sunroom was great for starting the day with coffee and finishing with adult beverages. The location was ideal...30 minutes or less to incredible hikes, breweries, wineries, and distilleries. Easy walk to Blue Mountain Brewery for dinner after a long day exploring the beautiful surrounding area.
Guest favourite
Home in Wintergreen Resort
4.95 out of 5 average rating, 222 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

SheillaRating, 5 stars2 weeks ago
Our family really enjoyed staying at the Salt Box!! The house was full of character and so much fun! We definitely would love to stay there again!!

Kid-Friendly apartment rentals

Top Guest favourite
Apartment in Staunton
4.99 out of 5 average rating, 124 reviews

Queen City Hideaway

SandyRating, 5 stars1 week ago
Desire and Scottys place was even cuter than the pictures. it had everything we needed and things we didn't realize that made our stay a home away from home. It was a peaceful place to relax in after a day of hiking and wineries in the area. It was also nice to be able to walk to dinner and explore town. Will definitely come back when we are in the area again.
Guest favourite
Apartment in Wintergreen Resort
4.93 out of 5 average rating, 135 reviews

Stone Ridge at Wintergreen

Abiyah BathRating, 5 stars1 month ago
This place was awesome! Clean and quiet with some amazing views. There’s an abundance of wild life so be mindful when driving. The host is amazing. There’s hot chocolate and a beautiful fire place. Blankets if you choose to sit on the balcony with some hot chocolate and enjoy the view. Many food choices to choose from that aren’t too far. Would definitely stay here again and recommend you do too.
Guest favourite
Apartment in Staunton
4.93 out of 5 average rating, 560 reviews

Lewis Creek Loft

DennisRating, 5 stars2 weeks ago
The stay at Laurie’s was great and she was super helpful dealing with our admittedly messy scheduling. The location is great by the wharf and while there is some noise due to the age of the building we were not bothered at all and slept great, we would definitely stay here again!
Top Guest favourite
Apartment in Staunton
4.94 out of 5 average rating, 171 reviews

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

Mary JaneRating, 5 stars2 days ago
This place is so cute, perfect for a one night getaway for me and my husband. For such a small space it really delivered with all the amenities we needed for a comfortable stay. Would gladly stay again if we ever make it back to Staunton!
Top Guest favourite
Apartment in Staunton
5 out of 5 average rating, 270 reviews

The Downtown Corner Place - Location and Luxury

TomiRating, 5 stars1 month ago
Fun weekend trip! I was in Staunton for a show at the American Shakespeare Center and stayed an extra day to explore the area. It just happened to be opening weekend for the farmer's market as well as the start of the outdoor shopping/dining season on Beverley Street. Martha's place is the perfect central location for exploring this very walkable town - I enjoyed seeing the Woodrow Wilson Museum (and garden in the back with lots of spring flowers blooming), Mary Baldwin campus, Trinity Church, etc. Martha's apartment is so comfy and clean, and has all the amenities. The bed is amazingly comfortable, the kitchen is well equipped, and the living room couch/tv setup is nice for relaxing with a show or movie in the evening. There are so many little touches throughout the apartment that let you know that Martha has thought of everything to make her guests feel at home. I can't say enough about this charming place and wonderful host!
Top Guest favourite
Apartment in Staunton
4.98 out of 5 average rating, 331 reviews

The Bons Amis Suite: Walk Downtown!

TheresaRating, 5 stars1 week ago
Our stay was very comfortable and the well appointed room was perfect! We were in town for the VA Garden Tour. Felt like we were in Paris with the custom decor! Conveniently located within walking distance to downtown shops and restaurants. The kitchen area was spotless and well stocked. I would recommend to anyone visiting Staunton. Merci beacoup for a wonderful stay!
Guest favourite
Apartment in Afton
4.97 out of 5 average rating, 176 reviews

Mountain View Getaway

LauraRating, 5 stars1 week ago
We had a wonderful stay. The location is off of a quiet road on a peaceful and beautiful piece of land. We loved meeting the goats (with two only hours-old babies to boot!) and pigs - and Dalva of course. The living space is clean and has everything you could need. Above all, having welcoming hosts is what makes an AirBnb stand out. Thank you both again!
Guest favourite
Apartment in Staunton
4.97 out of 5 average rating, 256 reviews

⭐Private Apartment Footsteps From Downtown

KimberlyRating, 5 stars1 day ago
Truly one of the cleanest, most attractive rentals I’ve stayed in. The hosts were proactive in sending very clear instructions on how to access the unit and where to park. The apartment itself is very comfortable and ideal for one or two people. But the wrap around porch with cozy chairs on this elegant old house is paradise! Lovely view and so many songbirds! The location is a pleasant short walk to downtown. I can see why they have so many repeat customers. Count us in!

Child-Friendly Holiday Condos

Guest favourite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 219 reviews

The Modern Mountain Condo

AmandaRating, 5 stars2 weeks ago
Loved this little condo! It’s perfect for a weekend away. The market is a minute walk away, it was so clean and cute, and the bed was so comfy and cozy too. Would absolutely return!
Guest favourite
Condo in Wintergreen Resort
4.95 out of 5 average rating, 129 reviews

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

WhitneyRating, 5 stars2 months 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 stars2 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)
Top Guest favourite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 205 reviews

New Construction! 1 Bed/2 Bath, pet friendly

AmandaRating, 5 stars1 month 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 stars2 months 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 stars1 month 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, 246 reviews

Cozy, clean, quiet mountain condo- King bed

ChristieRating, 5 stars2 weeks ago
Ritta's condo is clean, spacious and comfortable, situated in a woodland sanctuary of peace and quiet. Loved each morning and evening of spacious solitude.
Top Guest favourite
Condo in Wintergreen Resort
4.98 out of 5 average rating, 134 reviews

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

LaurenRating, 5 stars1 week ago
Mary’s place was exactly what we needed for our family with small children. The kids loved eating on the deck and being able to sleep in the same room but in their own bed. They had games available and everything was nice and clean. Mary was also quick to respond with any questions we had. We would definitely stay here again!

Quick stats about holiday rentals that are kid-friendly in Wintergreen Resort

  • Total rentals

    170 properties

  • Nightly prices starting at

    $123 AUD before taxes and fees

  • Total number of reviews

    9.2K reviews

  • Family-friendly rentals

    160 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with a pool

    100 properties have a pool

Destinations to explore