
Family-friendly holiday rentals in Wintergreen Resort
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Wintergreen Resort
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Close to skiing! | King Beds | Fireplace | Hot Tub
Welcome to Blackrock Escape! Dog friendly, 2BR/2.5BA mountain home in prime location at Wintergreen Resort. 3-min drive to the Mountain Inn. Walk to hiking trails–the Plunge Trail/Blackrock Park is only a 2-min walk. Two BRs on first floor - both with King-size Helix mattresses, smart TVs, and en suite bathrooms. Wood burning fireplace, games, puzzles, 65” smart TV in living room. Two decks w/gas grill and hot tub. Keurig K-Duo coffee maker and dishwasher in kitchen. Full-sized washer and dryer.

Tips Up: Cozy Slopeside Retreat w/ Fireplace
The mountains are calling and you must go. Well, you don't have to, but we think it's a good idea. Make Tips Up your home while you're away. With slopeside views, a cozy and comfortable ambiance, and close proximity to skiing (only 100 yards from the slopes!) and hiking, this 1B/1BA condo is the perfect getaway for outdoor enthusiasts seeking a mountain escape. Relax at nearby breweries and wineries with unbeatable views, and return to your condo to enjoy the amenities of Wintergreen Resort.

Panoramic Sunsets, Mountain Views, Private Deck.
Wake up above the mountains and end your day with unforgettable sunset views some of the best on the mountain. Sunset Vista Villa is a cozy retreat designed for slowing down, morning coffee on the deck, evenings by the fire. With two private bedrooms, each with its own en-suite bathroom, its perfect for couples or friends. Easy entry with just a few steps, yet elevated views make this stay both convenient and special. Ask us about early check-in or late check-out to enjoy even more of the view

NO STEP ENTRY Wintergreen Mtn Home,HotTub,Sleeps10
We had to create a new listing for this property. Previous listing had 70+ reviews with a 4.8 Star rating. Same great host and same great house, just a new listing. Screenshots of old listing in additional photos. Stay at this luxurious 4-bedroom, 3-full bath vacation rental home for 10 in Wintergreen, within minutes of top-notch golf courses, skiing / snow boarding at the Mountain Inn, and dozens of hiking trails . In addition to the unbeatable location, the property offers a private hot tub!

Five Minute Walk to Everything!
**Pet friendly** two bedroom, two bath, loft style condo centrally located at Wintergreen Resort. Ski check-in/lifts, restaurants, the mountaintop provisions market, and the Mountain Inn and conference center are all within a 5 minute walk! This is a two-story unit with loft style bedroom and en suite bath, and first floor bedroom with hall bath. Parking, pool access, washer/dryer, and Wi-Fi included. Fully stocked kitchen, wood burning fireplace, balcony, all towels/linens provided. Sleeps 5.

The Cottage at Spindle Hill: an Artist’s Farm
A handcrafted cottage on a small historic artist's farm, built of salvaged materials and sustainably forested Virginia timber — featured in design blogs, stocked with genuine care, and unlike anything else you'll find on here. Cedar hot tub. Record player. Fresh eggs. Homemade granola. Beautiful gardens, hammocks, and a 200-year-old White Oak. Minutes to Devils Backbone, Bold Rock, the Blue Ridge Parkway, and the Appalachian Trail. High-speed fiber. Library. Hens. Miniature Goats. EV Charger.

Luxury Condo in the Sky! Finest in Wintergreen!
Welcome to our recently renovated luxury condo in the sky! Perched on the edge of the Wintergreen ridgeline, we are just a stone’s throw from nature’s bounty. Our condo offers the perfect blend of relaxation and access to recreation. Hit the ski slopes, take a hike, or explore the bountiful brew and wine scene and then come enjoy the view. The horizon is 75 miles distant from our balcony on a clear day! We love hosting families with kids or couples coming to enjoy all that Wintergreen offers!

1 bedroom condo, walk to the slopes !
Cozy 1BR Wintergreen condo ⛷️❄️ 5-minute walk to the ski slopes, resort village, and mountain-too market, with snow tubing only minutes away. Enjoy a fully stocked kitchen, premium coffee and teas, cooking oils and spices. Relax by the wood burning fire and enjoy a smart TV, fast WiFi and games. Comfortable queen bed in the bedroom plus new queen sleeper sofa in the living room. Private furnished patio with peaceful wooded views and close access to the village for après-ski.

Cliffs Edge -A Contemporary Mountain Home
An open floor plan with high ceilings and large skylights, this amazingly engineered home will stun you with its incredible mountain views! This spacious home, with its cantilevered decks, makes this perfect for any family. The large upstairs loft, adjacent to the upstairs bedrooms, offers movies, games, puzzles, and comfortable seating. Wi-Fi, Netflix, and Samsung Smart hub give plenty of entertainment options. The spacious living area and dining room have abundant seating for all.

Stylish 7BR/16 pp Wintergreen Resort Home Ski/Hike
7BR/ 6.5B perfect mountain getaway! Tucked away in the woods & situated on 1/2 acre lot, this peaceful escape is less than 5 min from skiing, hiking, spa, pool, tennis & activity center w/i Wintergreen Resort. This spacious home feat. new ss appl, new furniture, HW flrs, granite cntrs, deck w/new grill, open flr plan, 75” tv, new outdoor furniture, new washer/dryer, darts, games/puzzles & new ping pong table. 6 BRs have en-suite baths & 4 have tvs; very private for large grps.

The Sanctuary
Nature lovers paradise! Named "The Sanctuary" for the place you can UNPLUG, unwind & find your peace! Perched up high on nearly 60 acres- you are sure to get fresh air & the rest you are searching for! Only 4 miles to Wintergreen, 6 miles to Sherando lake and backs up to the Blue Ridge Parkway there are plenty of things to do OR just relax and enjoy the crickets & stars! With crazy careers, growing kids & constant hustle- everyone needs a hide out like this every now and then!

Modern Cabin with Hot tub and Sauna
Welcome to Blue Ridge Hollow! This designer-decorated cabin in the heart of Wintergreen has one of the best outdoor spaces in the area. Relax in the hot tub or cedar barrel sauna, then enjoy a meal at the oversized outdoor table or sip wine around the firepit. The updated kitchen is fully stocked and open to the living room and sun-drenched dining room. 3 bedrooms are masters, the others share a bathroom, and the downstairs game room can be a 6th bedroom. Plus, pet friendly!
Popular amenities for Wintergreen Resort family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy 5-bedroom home for large gatherings.

Modern cabin, hot tub, mtn views, fireplace

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Private Pool Opens April 1 - All Year Hot Tub

Luxe Yurt w/Hot Tub in the Heart of the Blue Ridge

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

Luxury Mountain Lodge: Hot Tub & EPIC Views!

Misty Mountain Cabin w/spa
Family- and pet-friendly home rentals

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

“Small" House/Peaceful/Brewery/Hike/Winery/River

Luxury Tiny Home: Cozy, Modern Luxury Tiny Retreat

1720 High Ridge at Wintergreen Resort

Wintergreen home, ideal location, dogs welcome!

New Construction! 1 Bed/2 Bath, pet friendly

The Bear Dance Cabin at Wintergreen Resort

Cabin Escape | Family & Dog Friendly | Fire Pit
Family-friendly home rentals with a pool

The Modern Mountain Condo

Cozy Condo - Sleeps 4

Wintergreen Mountain Views - Diamond in the Slopes

Buena Vista Panoramic Retreat: Million Dollar View

Panoramic Peak: Wintergreen Condo with Views

Cozy 3BR/2BR+Fire table+Foosball

Mountain Bauhaus | Sleeps 8 | Amenities | Grill

2-min drive to resort, stair-free/free firewood!
When is the best time to visit Wintergreen Resort?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $358 AUD | $347 AUD | $292 AUD | $278 AUD | $301 AUD | $275 AUD | $287 AUD | $270 AUD | $267 AUD | $321 AUD | $325 AUD | $404 AUD |
| Avg. temp | 2°C | 4°C | 8°C | 14°C | 18°C | 22°C | 24°C | 23°C | 20°C | 14°C | 9°C | 4°C |
Quick stats about holiday rentals that are family-friendly in Wintergreen Resort

Total holiday rentals
Explore 560 holiday rentals in Wintergreen Resort

Nightly prices starting at
Wintergreen Resort holiday rentals start at $128 AUD per night before taxes and fees

Verified guest reviews
Over 22,640 verified reviews to help you choose

Pet-friendly accommodation
Find 230 rentals that welcome pets

Holiday rentals with a pool
340 properties feature pools

Rentals with dedicated workspaces
240 properties have a dedicated workspace

Wi-Fi availability
560 of Wintergreen Resort holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Wintergreen Resort rentals

4.9 Average rating
Wintergreen Resort stays are highly rated by guests—averaging 4.9 out of 5!
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- Shenandoah National Park
- Early Mountain Winery
- Downtown Mall
- James Monroe's Highland
- Wintergreen Resort
- Frontier Culture Museum
- Homestead Ski Slopes
- Blenheim Vineyards
- Amazement Square
- Devils Backbone Brewing Co Basecamp
- Cardinal Point Winery
- Liberty Mountain Snowflex Centre
- John Paul Jones Arena
- Glass House Winery
- Monticello
- University of Virginia
- Virginia Horse Center
- James Madison University
- The Rotunda
- Grand Caverns
- White Lotus Eco Spa Retreat
- IX Art Park
- James Madison's Montpelier
- James River State Park




