Kid-friendly vacation rentals in Wintergreen Resort

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Popular amenities for Wintergreen Resort kid-friendly rentals

Kid-friendly house rentals

Guest favorite
The exterior of a multi-level home is nestled among trees, with warm lighting illuminating the porch and deck. The spacious deck features a staircase leading down, surrounded by autumn leaves, creating a welcoming atmosphere.
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 favorite
A cozy room is characterized by a unique, colorful teepee and a sleek multifunctional sofa. Light streams through a curtain-covered window, illuminating the wood-paneled walls. A modern light fixture adds a playful touch, while a textured rug anchors the space.
Home in Nellysford
4.97 out of 5 average rating, 136 reviews

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

BrittanyRating, 5 stars6 days 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!
Top guest favorite
A charming three-bedroom home is surrounded by lush gardens filled with colorful flowers and vibrant greenery. Towering hills rise in the background, while a variety of trees and shrubs add to the scenic landscape of the property.
Home in Lovingston
4.93 out of 5 average rating, 150 reviews

Three Springs with EV charging station

HeleneRating, 5 stars3 weeks 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 favorite
Home in Crozet
4.97 out of 5 average rating, 197 reviews

Crozet casa w/ firepit & hot tub in wine country

MeganRating, 5 stars1 month 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 favorite
Home in Crozet
4.97 out of 5 average rating, 105 reviews

"The Shire" at Hollow View: Crozet Farmhouse

JodiRating, 5 stars1 month ago
Great farm house and wonderful experience. Was so nice to be able ti being the dogs. They loved the field.
Guest favorite
A ping pong table is positioned in a relaxed game room, surrounded by softly lit walls and wooden doors. A folding chair is visible nearby, adding functionality to the space. The carpeted floor enhances comfort for casual play.
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 favorite
A living room is presented with a large, brown leather sofa in the foreground. An angular coffee table occupies the center, surrounded by two patterned armchairs. A television is positioned on a dark wood media console against a wall, with a potted plant adding a touch of greenery near a window dressed with light curtains.
Home in Afton
4.96 out of 5 average rating, 241 reviews

CritzerHouse - on 151- Walk to the Brewery!

KarenRating, 5 stars1 week 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 favorite
The exterior of a modern home is surrounded by lush green trees, blending harmoniously with the natural landscape. The house features a geometric design with multiple windows, enhancing the connection to the outdoors. A gravel path leads up to the entrance, framed by the forest.
Home in Wintergreen Resort
4.95 out of 5 average rating, 221 reviews

Saltbox at Wintergreen, a Modern Mountain Escape

LinaRating, 5 stars2 months ago
We loved Saltbox! Kristy was a great and very responsive host. We enjoyed the layout and cleanliness of the house, as well as it’s closeness to Wintergreen. We would definitely stay here again.

Kid-friendly apartment rentals

Guest favorite
A wooden deck is elevated and features a vibrant red umbrella. Surrounding the deck are leafy green plants and a small seating area with pink chairs. A lattice design is present under the deck, adding texture to the space.
Apartment in Lovingston
4.89 out of 5 average rating, 136 reviews

Lovingston Get-Away Lovingston, VA

JacquelynRating, 5 stars2 months 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 favorite
Apartment in Staunton
5 out of 5 average rating, 123 reviews

Queen City Hideaway

SandyRating, 5 stars2 days 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 favorite
A modern living area features a grey sofa with decorative pillows, complemented by a glass coffee table. Two art pieces hang on the wall above, and plants are positioned throughout. Seating includes two stylish chairs and soft ottomans, all arranged on a geometric-patterned area rug.
Apartment in Wintergreen Resort
4.93 out of 5 average rating, 135 reviews

Stone Ridge at Wintergreen

Abiyah BathRating, 5 stars2 weeks 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 favorite
The living area features a light-colored sofa paired with a red storage ottoman at the center, providing a comfortable seating arrangement. A rocking chair and bookshelf enhance the space, with a large artwork displayed on the wall. Natural light enters through the windows, illuminating the warm wooden floors.
Apartment in Staunton
4.93 out of 5 average rating, 559 reviews

Lewis Creek Loft

DennisRating, 5 stars1 week 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 favorite
A comfortable living area is furnished with a dark sofa adorned with textured cushions. Two light-colored armchairs are positioned nearby, and a small side table holds a plant. Natural light floods the space through large windows, illuminating the patterned area rug.
Apartment in Staunton
4.94 out of 5 average rating, 166 reviews

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

ElizabethRating, 5 stars1 week ago
A home away from home. Susan has thought of the little things one needs when traveling. Her place is extremely clean, lovely space, and the perfect walk from everything Staunton has to offer. It's our 4th or 5th time staying with her- enough said.
Top guest favorite
A living area features a dark wooden coffee table surrounded by two red armchairs and a sofa. A wooden dresser stands against the wall, and a decorative wall art piece adds color. The entrance to a kitchen is visible through an open doorway.
Apartment in Staunton
5 out of 5 average rating, 269 reviews

The Downtown Corner Place - Location and Luxury

TomiRating, 5 stars2 weeks 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 favorite
A spacious living room features a comfortable sofa adorned with decorative pillows, a light-colored coffee table, and a patterned area rug. The room is complemented by a decorative brick accent wall and a chandelier, with natural light filtering through sheer curtains on a large window.
Apartment in Staunton
4.98 out of 5 average rating, 329 reviews

The Bons Amis Suite: Walk Downtown!

DeniseRating, 5 stars2 weeks ago
Jamie's space is super clean and comfortable. It was obvious that the hosts devoted much care and attention to their guests’ needs. The photos are accurate, with the apartment being even more lovely in person. Easy walk to downtown and many Staunton attractions. We parked in the gravel lot behind the house since it was mostly empty. The driveway is narrow with a steep-ish decent into the lot. (It’s Staunton - the whole town is hilly.) But, for those who don’t want to do that, there were spots on the street. Would stay here again.
Guest favorite
A comfortable seating area features a gray sofa adorned with patterned cushions, complemented by a wooden coffee table holding various magazines. A large mirror hangs above the sofa, reflecting light in the space, while light-colored walls and warm wood flooring create a cozy ambiance.
Apartment in Afton
4.97 out of 5 average rating, 174 reviews

Mountain View Getaway

ElizabethRating, 5 stars5 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!

Kid-friendly condo rentals

Guest favorite
A spacious living area features a wood-burning fireplace surrounded by light-colored walls. A comfortable couch, adorned with a welcoming throw pillow, faces a wooden coffee table. Natural light enters through large windows, offering views of the outdoor greenery.
Condo in Wintergreen Resort
4.94 out of 5 average rating, 218 reviews

The Modern Mountain Condo

KileyRating, 5 stars1 week ago
Had a great stay for a few nights in this condo. Comfortable and clean as a lovely escape while we enjoyed local hikes and breweries. Convenient to the wintergreen market which was helpful for what we may have forgotten or for anything else we wanted. Looooved having the wood burning fireplace too! We’d love to come back.
Top guest favorite
An inviting living space features a comfortable sectional sofa arranged around a round coffee table, complemented by a cozy rug. A gas fireplace is framed by white paneling, and large windows provide ample natural light while showcasing views of the surrounding landscape.
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 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 favorite
The living area features comfortable leather seating arranged around a wooden coffee table. A fireplace is visible, surrounded by a stone accent, and large windows allow natural light to fill the space, offering views of the outdoors.
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 favorite
A comfortable living area features a spacious gray sofa and a wooden coffee table, positioned on a patterned rug. Light from a nearby lamp and large sliding doors illuminates the space, which offers views of the outdoors. A cozy accent chair completes the inviting setup.
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 favorite
A modern living space is presented with large floor-to-ceiling windows offering views of the landscape. A sleek fireplace is positioned against a stone accent wall, while comfortable seating includes a leather sofa and a woven armchair. A soft rug covers the floor, adding warmth to the area.
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 favorite
A balcony view captures rolling green hills beneath a layer of clouds, with distant mountain peaks rising above. A wrought iron dining set is present on the balcony, providing a serene space for enjoying the landscape.
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 favorite
Condo in Wintergreen Resort
4.94 out of 5 average rating, 246 reviews

Cozy, clean, quiet mountain condo- King bed

ChristieRating, 5 stars6 days 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 favorite
A private balcony features wooden railings, with a light dusting of snow on the ledge. Lush pine trees stand prominently in the background, contrasting against a clear blue sky and hints of distant landscape, contributing to a serene outdoor viewing experience.
Condo in Wintergreen Resort
4.98 out of 5 average rating, 133 reviews

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

AlexisRating, 5 stars1 week ago
We had the pleasure staying here for 3 nights. The condo is beautiful, clean, and in an amazing location. Mary was very responsive and provided wonderful recommendations in the area. I would recommend this lovely place to anyone looking for a getaway at Wintergreen and we will definitely be returning in the future!

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

  • Total rentals

    170 properties

  • Nightly prices starting at

    $80 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