Kid-friendly holiday rentals in Wintergreen Resort

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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, 132 reviews

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

ChrisRating, 5 stars3 weeks ago
The place was great, easily accessible and as described. Very clean and well put together. Stocked with everything you may need and more. Our car broke down on the way up and the host(s) even offered to help with that. Overall super pleasant experience would recommend!
Guest favourite
Home in Nellysford
4.97 out of 5 average rating, 134 reviews

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

LynetteRating, 5 stars4 days 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!!
Guest favourite
Home in Lovingston
4.93 out of 5 average rating, 149 reviews

Three Springs with EV charging station

MicheleRating, 5 stars3 months ago
Deborah was very responsive from day 1 until after check out, even when I asked for advice on a local place to host a Rehearsal Luncheon. Her house was beautiful and peaceful! There was plenty of room to spread out and relax. The property was GORGEOUS! I wish I could've spent more time there. I hope to go back again sometime!
Guest favourite
Home in Crozet
4.97 out of 5 average rating, 193 reviews

Crozet casa w/ firepit & hot tub in wine country

JosiahRating, 5 stars1 week ago
Bevin was a fantastic host! Her home was warm, inviting and clean. I would happily stay at her home in the future. Thank you for a great stay!
Guest favourite
Home in Nellysford
4.99 out of 5 average rating, 101 reviews

Mountain Season Lodge

CarolynRating, 5 stars5 days 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.
Superhost
Home in Waynesboro
4.83 out of 5 average rating, 120 reviews

Hot Tub - Fire Pit - Game Room

KaraRating, 5 stars1 week ago
Nice place to stay. We enjoyed the hot tub and lounging around the house during a snowstorm. Mack was extremely responsive to the few quetions we had!!
Guest favourite
Home in Afton
4.96 out of 5 average rating, 232 reviews

CritzerHouse - on 151- Walk to the Brewery!

LisaRating, 5 stars3 weeks ago
We wanted a Wintergreen weekend and this house was located perfectly! This was a perfect house for our group! We all loved how beautiful the decorations are! The kitchen was well stocked, bathrooms were very clean down to all the linens! Beds were comfortable. Our grandson enjoyed coloring and playing with the toys. No issue with internet. We even watched a few movies while we were there. Thank you so much for a great stay! We definitely will stay again!!
Guest favourite
Home in Wintergreen Resort
4.95 out of 5 average rating, 217 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

JosephRating, 5 stars3 weeks ago
Kristy was a fantastic host that responded quickly with all the necessary details! The location is great, with convenient access to the Wintergreen Resort. It comfortably fit 8 adults and you could easily put out a couple air mattresses for kids. Beds were very comfortable and kitchen had everything we needed. The common areas can get a little chilly due to the design of the house but having a heater at the bottom level paired with the central heating provides for a warm space! The driveway is a bit steep and can get icy which can be trickier to pull out of without 4WD, but there is plenty of street parking in front of the house. This was all communicated beforehand as well. I would highly recommend Saltbox to anyone looking for a convenient stay to Wintergreen resort!

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 stars5 days 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.
Guest favourite
Apartment in Wintergreen Resort
4.85 out of 5 average rating, 121 reviews

Walk to Market/Slopes!

McKenzieRating, 5 stars1 month ago
Perfect for a long weekend! Easy to walk to the market and slopes
Guest favourite
Apartment in Staunton
4.99 out of 5 average rating, 399 reviews

Wildflowers Artist House

JanelleRating, 5 stars1 month ago
Beautiful listing and very communicative hosts. It was snowing outside for most of our stay so it wouldn’t have been easy to get in and out of the listing due to potentially icy conditions, but we didn’t mind. We brought our food and had an absolute blast enjoying the space and nature spotting from the windows. Thank you, Sharon!!
Guest favourite
Apartment in Crozet
4.9 out of 5 average rating, 29 reviews

Piedmont Place 401 | Modern Apt | Near KFV

PerryRating, 5 stars4 months ago
We had a wonderful time. It was a great place to stay close to wineries and breweries.
Guest favourite
Apartment in Wintergreen Resort
4.92 out of 5 average rating, 128 reviews

Stone Ridge at Wintergreen

KristinRating, 5 stars6 days ago
Chrisy’s place was clean, cozy, and super cute! She was very responsive to questions or concerns and went out of her way to fix any issues (ie. replaced malfunctioning washing machine). The foosball table and hot chocolate were a hit with our kids. Thank you for sharing your place with us!
Superhost
Apartment in Waynesboro
4.93 out of 5 average rating, 312 reviews

Mimosa Farm *no cleaning fee for 2+ day stays*

LiisaRating, 5 stars2 months ago
Jill's place was very convenient for our son & his family on a recent visit. The kids enjoyed seeing the goats. Would definitely rent again in the future.
Guest favourite
Apartment in Crozet
5 out of 5 average rating, 24 reviews

Mtn Vineyards Getaway

ChristinaRating, 5 stars3 months ago
This apartment was super clean and beautiful. Great stay for one night with my girlfriends needing a place to stay after winery hopping! The host was super responsive to any questions we had and accommodating to our needs. Very safe a beautiful neighborhood. Would recommend this place to anyone who needs a place to stay just outside Charlottesville!
Guest favourite
Apartment in Rockfish
4.98 out of 5 average rating, 181 reviews

Blue Ridge Bliss - For family & friends to enjoy!

CristineRating, 5 stars3 weeks ago
One word: WOW! We felt right at home in this gorgeous place. It had everything and more for what we needed. The kitchen was fully equipped, hair dryers in each bathroom and logs for the fire. A king size bed was very much appreciated and very comfortable. The view of the sun rising over the mountains was incredible as well and made the stay totally worth it! We are looking forward to coming again.

Child-Friendly Holiday Condos

Guest favourite
Condo in Wintergreen Resort
4.98 out of 5 average rating, 186 reviews

Cozy getaway with heated floors

JenniferRating, 5 stars2 weeks ago
Everything was perfectly appointed and well stocked. All the little things were thought of and provided. Super communicative host, great place to stay.
Guest favourite
Condo in Wintergreen Resort
4.95 out of 5 average rating, 207 reviews

The Modern Mountain Condo

KellyRating, 5 stars1 week ago
My partner and I truly enjoyed ourselves here. It is a beautiful Airbnb and very cozy. 10/10 would recommend staying here for couples and families.
Guest favourite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 127 reviews

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

WhitneyRating, 5 stars5 days 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!
Superhost
Condo in Wintergreen Resort
4.88 out of 5 average rating, 112 reviews

1720 High Ridge at Wintergreen Resort

Robert Rating, 5 stars1 month ago
Great condo with fantastic views!
Guest favourite
Condo in Wintergreen Resort
4.96 out of 5 average rating, 201 reviews

New Construction! 1 Bed/2 Bath, pet friendly

CamRating, 5 stars3 weeks ago
For starters, thank you for allowing my good boy (Golden retriever) to stay . We all had a great time . Beautiful place located perfectly in devils knob, near everything you need on the resort . Looking forward to spending more nights there! Thanks Lisa!
Guest favourite
Condo in Wintergreen Resort
4.95 out of 5 average rating, 175 reviews

Ski-in/Ski-out Wintergreen Highlands Condo -Views!

MikeRating, 5 stars1 month ago
Our family had the best stay at Lindsay's place. Everything we needed was provided. We cooked in the kitchen and wanted for nothing. Our weather was terrible the first couple of days, and ski conditions were not great those days, but we hunkered down and had a great time anyway. Our son had the flu and we had to delay our trip a day, and Lindsay was very accommodating. My family doesn't travel much beyond the beach, so our expectations were high for a great mountain trip. We all had a blast!
Guest favourite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 242 reviews

Cozy, clean, quiet mountain condo- King bed

VictoriaRating, 5 stars1 week ago
Ritta's place is cozy and comfortable, convenient to Wintergreen and the Appalachian Trail. Check-in was easy and Ritta was proactive with communication and responsive when we had questions. We enjoyed the fireplace, games, and beautiful surroundings. Thanks for a great stay!
Guest favourite
Condo in Wintergreen Resort
4.98 out of 5 average rating, 126 reviews

2-min drive from ski slopes/hiking, free firewood!

Soo JungRating, 5 stars2 days ago
Mary was a great host. The unit was very nice and as described in the post. Very convenient to the slopes. We ended up getting there early and she allowed us to checkin early. However cleaning crew was still there so we ended going somewhere to eat close by. Mary was also very responsive and polite. My only issue with the place was the HVAC. It was very loud at night so it was difficult to get peaceful sleep. I would let this deter me from renting again though.

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