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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

Top Guest favourite
Home in Wintergreen Resort
4.88 out of 5 average rating, 136 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

KatieRating, 5 stars3 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!
Top Guest favourite
Home in Lovingston
4.96 out of 5 average rating, 210 reviews

Cottage on the Knoll ~ Prvt Pool & Hot Tub OPEN

JaniceRating, 5 stars1 month ago
A great choice in this area. The house is spacious, clean and comfortable with a lot of amenities. Nice layout for families or groups. We enjoyed coming back after busy days to a relaxing environment. Hosts were very communicative and accommodating. Would definitely stay again.
Superhost
Home in Wintergreen Resort
5 out of 5 average rating, 3 reviews

Casa Perfecta

JosephRating, 5 stars3 weeks ago
We had an amazing stay at this beautiful condo in the mountains! The location is perfect for anyone looking to hit the slopes or tour the grounds – making it great destination year round. The condo itself is cozy, clean, and has everything you need for a comfortable stay. The kitchen was well-equipped, which made it easy to cook meals before heading out for the day. The beds were super comfortable, and we slept like babies every night! The host was incredibly helpful, providing us with all the information we needed for the resort, and even sent us local recommendations for dining and things to do in the area. Check-in and check-out were a breeze. Would definitely recommend this place to anyone looking for a relaxing, convenient, and picturesque retreat. We’ll be back next year for sure!
Top Guest favourite
Home in Amherst
4.97 out of 5 average rating, 448 reviews

The Vixen House

LukeRating, 5 stars2 weeks ago
Wonderful, clean home to stay in. I’ve stayed here twice and would definitely book again!
Guest favourite
Home in Wintergreen Resort
4.96 out of 5 average rating, 106 reviews

Peaceful 3-BR Mountain home w/Fireplace + Hot tub

NikiRating, 5 stars2 months ago
Our family of four needed a quiet get away, and we enjoyed the beautiful days and evenings, inside and on the deck! Hikes nearby, spa nearby, restaurants, grocery, gas also nearby. Great resort year round! Lots of activities if you want them, and lots of peaceful nature if you want. Great!
Top Guest favourite
Home in Nellysford
4.97 out of 5 average rating, 147 reviews

Glass House | Mountain & Water Views @ Wintergreen

DongmeiRating, 5 stars3 weeks ago
A very nice spacious house that suit our family perfectly, hosts are very responsive, they always got back to us right away. We had a great Memorial weekend in glass house, highly recommended to other travelers!
Top Guest favourite
Home in Nellysford
5 out of 5 average rating, 19 reviews

"Glass & Pine" Home close to Bold Rock &Vineyards

SaraRating, 5 stars1 week ago
Lovely place, very clean, stylishly decorated. It is roomy and has a fantastic view. Nice outdoor sitting areas. It is secluded. The only problem my family and I ran into was knowing what driveway to turn in. We failed to see a sign that displayed a house number at the end of the driveway. Other than that the house and our stay was outstanding.
Top Guest favourite
Home in Nellysford
4.99 out of 5 average rating, 114 reviews

Wooded Haven | Family Friendly | Fire Pit | Trail

DanRating, 5 starstoday
We can’t say enough about our stay at The Wooder House. The home was perfect for our group of six, giving us all our own space to retreat while also offering large spaces to enjoy meals and movies together. Our kids loved the collections of board games, vinyl records and Calvin & Hobbes books. Everything we needed was readily available and thoughtfully organized, and Amy was such an attentive and kind host for our entire stay. Our visit revolved around hiking in Shenandoah, so the home was a great base camp for our adventures. It’s about a 30 minute drive to the south entrance of the park, and 20 minutes to a variety of breweries, coffee shops and vineyards. We truly can’t wait to visit again.

Kid-Friendly apartment rentals

Top Guest favourite
Apartment in Staunton
5 out of 5 average rating, 136 reviews

Queen City Hideaway

CatherineRating, 5 stars5 days ago
My husband and I decided to extend our honeymoon stay in the area and the lodging we had been staying at couldn’t host us for the extra day, which is how we came to find this gem! We loved this apartment and wished we could have stayed longer! The location was great and the home itself was just STUNNING. From the low lights & jazz music playing on arrival, to the cute & homey decor, to all the extras (robes, espresso, cozy blankets), this place completely impressed us. Oh, and the outdoor area was just an extra plus! The host was super responsive and sweet and couldn’t have possibly done anything better, it was all perfect! We would 100% recommend this stay and we hope to return for an anniversary trip!
Guest favourite
Apartment in Wintergreen Resort
4.85 out of 5 average rating, 124 reviews

Walk to Market/Slopes!

JimRating, 5 stars3 weeks ago
What a gem to find. My stay was comfortable, relaxing and perfect for me. This is on my return list. Thank you.
Guest favourite
Apartment in Wintergreen Resort
4.93 out of 5 average rating, 135 reviews

Stone Ridge at Wintergreen

Abiyah BathRating, 5 stars2 months 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.
Top Guest favourite
Apartment in Amherst
4.98 out of 5 average rating, 184 reviews

Welcoming Country Apartment

AudreyRating, 5 stars3 weeks ago
Visited Amherst for a family members graduation. Chose this location because it was very close to my family and was easy access for my husband who is in stroke recovery. We were met upon arrival and received a friendly greeting. Everything was clean and plentiful. Privacy was respected, they even had a few snacks available. I only had one issue with the lock and that was beyond their control. (Battery). I had to call them at midnight. I truly hated to wake them up but they were very nice and accommodating about the situation. If I find the need to stay in Amherst again I will check to see if there’s availability.
Top Guest favourite
Apartment in Crozet
5 out of 5 average rating, 489 reviews

The Barn at Haden near Wineries and C'ville

KristinRating, 5 stars3 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!
Superhost
Apartment in Afton
4.77 out of 5 average rating, 833 reviews

Studio Apt. in Wine/Brewery Country/on 151

AndreaRating, 5 stars6 days ago
Easy to find location using the directions provided. Self check-in lock easy to operate. Nice and clean location with rocking chairs outside you can sit and look at the amazing views.
Top Guest favourite
Apartment in Staunton
4.98 out of 5 average rating, 337 reviews

The Bons Amis Suite: Walk Downtown!

JoshuaRating, 5 stars5 days ago
Look no further than Bon Amis Suites for your stay in Staunton! The location is unbeatable, the bed and couch were so comfortable, parking is included, and the unit is well stocked with basics (coffee, shower soap, kitchen cookware, etc.). This was one of the best AirBnbs we’ve stayed in recently!
Top Guest favourite
Apartment in Staunton
4.98 out of 5 average rating, 107 reviews

Willow Ridge

SarahRating, 5 stars5 days ago
Beautiful view, great space, and close to downtown Staunton (10 min). The host is very responsive and accommodating! We were sad to leave and hope to return soon for a longer stay. Highly recommend!!

Child-Friendly Holiday Condos

Guest favourite
Condo in Wintergreen Resort
4.83 out of 5 average rating, 58 reviews

Cozy 1-bedroom Condo with Fireplace Near Ski Slope

JimRating, 5 stars2 months ago
Laleh is a great and perfect host. I have stayed with her numerous times and I have enjoyed her space, her continued communication and her quickness to address any number of questions. Enjoy your stay with her.
Top Guest favourite
Condo in Wintergreen Resort
4.95 out of 5 average rating, 296 reviews

Five Minute Walk to Everything!

CarolynRating, 5 stars3 weeks ago
This place was great! Conveniently located with tons of things to do, many walkable from the condo. The photos and descriptions were super accurate and our dogs even felt welcomed! We appreciated the convenience of The Market, The Edge, Upper Crust, and really enjoyed all of the Memorial Day activities that Dave ad Paige let us know were happening. It was the perfect place to unwind after a day of adventuring. Dave and Paige were super hosts all the way around. We'd love to come back here again!
Top Guest favourite
Condo in Wintergreen Resort
4.98 out of 5 average rating, 89 reviews

Wintergreen Resort King bed, Fire place, 2 Bd/2 Br

KimberlyRating, 5 stars1 week ago
Amanda's condo was clean and cozy. There are many nice upgrades in the space, including an updated kitchen, master bath, and modern furniture. We could easily find what we needed. We felt right at home and would love to stay here again!
Superhost
Condo in Wintergreen Resort
4.72 out of 5 average rating, 144 reviews

Mountain Views

DougRating, 5 stars1 week ago
We truly enjoyed our stay at Diana’s beautiful home. The scenery was absolutely stunning, and waking up to the sunrise each morning was a breathtaking experience. The home was comfortable, serene, and perfectly situated to enjoy the natural beauty all around. Highly recommend this wonderful retreat to anyone looking for a peaceful getaway.
Guest favourite
Condo in Wintergreen Resort
4.92 out of 5 average rating, 25 reviews

Wintergreen Mountain Views - Diamond in the Slopes

KateRating, 5 stars3 weeks ago
We loved our stay. It was exactly what we were looking for. The house is wonderful and very comfortable. Our kids loved the house, the area around it, and the hiking.
Guest favourite
Condo 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
Condo in Wintergreen Resort
4.88 out of 5 average rating, 163 reviews

Wander Lodge: Golf, Spa, Wine, or just a getaway

CatherineRating, 5 stars3 months ago
This was the perfect spot for our trip. A friend of mine and I brought our teenage sons for a quick weekend snowboarding trip, and needed somewhere with three sleeping areas. The loft had 2 beds and a fully bath which was exactly what we needed for the boys. It was super convenient to everything with a shuttle stop right out front. Plenty of parking, great amenities, clean, and easy to find! Also very cozy! We’ll definitely return!
Top Guest favourite
Condo in Wintergreen Resort
4.9 out of 5 average rating, 143 reviews

Cozy Comfort with a View - Wintergreen Resort

MeganRating, 5 stars3 weeks ago
We had a wonderful time while staying at this condo. There kitchen had plenty of pots and pans, the deck was relaxing, the bed we slept in downstairs was extremely comfortable. When Emile found out we were going to get in late, he had someone turn on the outside light. So nice because it would have been harder to get into the lockbox. So happy we stayed here for our getaway from the city.

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

  • Total rentals

    170 properties

  • Nightly prices starting at

    $133 NZD 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