Kid-friendly holiday rentals in Wintergreen Resort

Find and book unique family-friendly rentals on Airbnb

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Popular amenities for Wintergreen Resort family-friendly rentals

Kid-friendly house rentals

Top guest favourite
Home in Wintergreen Resort
4.96 out of 5 average rating, 105 reviews

Cliffs Edge- Hike, Play & Splash into Summer!

OmarRating, 5 stars1 month ago
Amazing place! My family and I thoroughly enjoyed our stay. Great home with breathtaking views of the Blue Ridge Mtns and tranquility for days! Julie was a superb host. Her hospitality, directions and communication were second to none. Thank you and we look forward to visiting again.
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 Wintergreen Resort
5 out of 5 average rating, 110 reviews

Cozy Chalet | King Beds | Fireplace | Hot Tub

KathrynRating, 5 stars1 week ago
Our stay here was awesome! Jayme was most attentive and responsive when needed. The house was fully equipped with all necessities so nothing was lacking. The peace, quiet, tranquility and beauty of the area makes visiting this place again a must!
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 stars4 weeks 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.
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
4.99 out of 5 average rating, 113 reviews

Forest Vibes | Family Friendly | Fire Pit | Trail

KatheleenRating, 5 stars1 week ago
Amy and Gareth made sure to think about every detail. They made sure that the purpose of our trip was celebrated. Amy provided a list of local recommendations and it was so helpful! The aesthetics of the house is also so natural and relaxing. There was no need to stress out about anything because the house came fully equipped. The walking path down to the river was also so beautiful! We cannot thank them enough for such a memorable time!
Guest favourite
Home in Wintergreen Resort
4.95 out of 5 average rating, 223 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

SheillaRating, 5 stars1 month 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!!

Family-friendly apartment rentals

Top guest favourite
Flat in Staunton
5 out of 5 average rating, 136 reviews

Queen City Hideaway

CatherineRating, 5 stars3 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!
Superhost
Flat in Afton
4.87 out of 5 average rating, 342 reviews

Best Spot on the Wine/Brew Trail!

JuliannaRating, 5 stars4 days ago
Lovely, quiet little spot about half a mile from Blue Mountain and ten minutes from the entrance to Skyline Drive. Very comfy mattress and the door is coded so you don’t have to worry about losing the key. would definitely stay again, thanks!
Guest favourite
Flat 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
Flat 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.
Guest favourite
Flat in Staunton
4.93 out of 5 average rating, 567 reviews

Lewis Creek Loft

KaitlinRating, 5 stars2 days ago
Loved our stay at Lewis Creek Loft! Laurie was an excellent host and the loft had all the amenities we needed. The loft is in a great location and is within walking distance of everything. We had a great weekend stay. Thanks so much, Laurie!
Top guest favourite
Flat in Staunton
4.97 out of 5 average rating, 435 reviews

The Bohemian Suite: Walk Downtown!

SierraRating, 5 stars2 weeks ago
The Bohemian Suite was such an absolute pleasure to stay in! When I walked in, I was immediately surrounded by an inviting space, colorful and fun decor, and beautiful signs everywhere with cute quotes. The bed was big and comfortable, the shower had great water pressure, the place was spotless. They thought of the details- had stocked the Keurig area, had a chess board set up to play, books in the reading nook, and even provided makeup towels! One thing I loved was that they did not have a TV out in the open, but did have one tucked away in a closet which was easy to roll out into whichever room you choose. Super clever and thoughtful! The ceilings in this suite were so high and gorgeous, it made the space feel huge. Walkable to everything in the town, easy parking, felt super safe and quiet. We absolutely were sad to leave to the Bohemian suite!
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 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!
Top guest favourite
Flat in Staunton
4.98 out of 5 average rating, 107 reviews

Willow Ridge

SarahRating, 5 stars3 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!!

Family-friendly apartment rentals

Guest favourite
Apartment 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.
Superhost
Apartment 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
Apartment 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
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
Apartment 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!
Guest favourite
Apartment in Wintergreen Resort
5 out of 5 average rating, 24 reviews

Love of mountains oh fill my cup

ChristinaRating, 5 stars3 weeks ago
Absolutely a gem!! Loved the super clean, comfortable (especially the huge soft sofa!) space. Kitchen had all the basics we needed, and everything worked as expected. Was the perfect location for our home base as we section-hiked the Appalachian Trail for a week. Would definitely stay again!
Guest favourite
Apartment in Wintergreen Resort
4.94 out of 5 average rating, 101 reviews

Mountain top 3-bedroom condo with spectacular view

AlyssaRating, 5 stars1 month ago
You don’t need many word for this place because it is STUNNING. Wonderful one day stay but goodness so worth it!
Guest favourite
Apartment in Wintergreen Resort
4.9 out of 5 average rating, 134 reviews

All season 3bd/3ba ski out/in - Location & Views!

JessicaRating, 5 stars3 weeks ago
Amazing view and condo! We loved our stay!

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

  • Total rentals

    170 properties

  • Nightly prices starting at

    ₹6,907 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

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