
Family-friendly vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Wintergreen Resort family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy 5-bedroom home for large gatherings.

Cottage on 151 w/ Hot Tub, Firepit, Mountain Views

Modern cabin, hot tub, mtn views, fireplace

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Cheerful 2 bd bungalow with HOT TUB! Pet friendly!

Ultimate cabin in the mountains

Cozy Cabin+Walk to Ski *Hot Tub* Mtn Vibe

Peaceful 3-BR Mountain home w/Fireplace + Hot tub
Family- and pet-friendly home rentals

Spacious Tiny Home Close to Wine, Beer & Mountains

LaCasadeChiChi

Eight Minute Walk to Everything

Mountain Views

Cabin in Woods | Family & Dog Friendly | Fire Pit

Sunrise Casita: a tiny house at Cana Barn

Tyro Mountain View Cabin

The Humble Abode Camp
Family-friendly home rentals with a pool

Cliffs Edge- It's Pumpkin Spice Time!

Wintergreen! Dog friendly, cozy and comfortable

Wintergreen Mountain Views - Diamond in the Slopes

Mountain View Nest

Buena Vista Panoramic Retreat: Million Dollar View

4 min to Ski! Mntn View Hot Tub EV Charger Grill

Your Favorite Getaway. EV charger- Walk to trails

Happy hour on the 18th Hole
Quick stats about vacation rentals that are family-friendly in Wintergreen Resort
Total rentals
550 properties
Nightly prices starting at
€ 77 before taxes and fees
Total number of reviews
22K reviews
Pet-friendly rentals
220 properties allow pets
Rentals with a pool
340 properties have a pool
Rentals with dedicated workspaces
230 properties have a dedicated workspace
Destinations to explore
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- Pet-friendly rentals Wintergreen Resort
- Rentals with outdoor seating Wintergreen Resort
- Cabin rentals Wintergreen Resort
- Rentals with a fire pit Wintergreen Resort
- Ski-in/ski-out rentals Wintergreen Resort
- Rentals with pools Wintergreen Resort
- Townhouse rentals Wintergreen Resort
- Apartment rentals Wintergreen Resort
- House rentals Wintergreen Resort
- Rentals with an EV charger Wintergreen Resort
- Rentals with a fireplace Wintergreen Resort
- Rentals with a washer and dryer Wintergreen Resort
- Rentals with a hot tub Wintergreen Resort
- Rentals with lake access Wintergreen Resort
- Rentals with a patio Wintergreen Resort
- Condo rentals Wintergreen Resort
- Family-friendly rentals Nelson County
- Family-friendly rentals Virginia
- Family-friendly rentals United States
- Massanutten Resort
- Omni Homestead Resort
- Early Mountain Winery
- Boonsboro Country Club
- Ash Lawn-Highland
- Amazement Square
- Homestead Ski Slopes
- Massanutten Ski Resort
- Chisholm Vineyards at Adventure Farm
- Frontier Culture Museum
- Spring Creek Golf Club
- Liberty Mountain Snowflex Centre
- The Plunge Snow Tubing Park
- Wintergreen Resort
- Blenheim Vineyards
- Farmington Country Club
- Birdwood Golf Course
- Glass House Winery
- Cardinal Point Winery
- Burnley Vineyards
- Meriwether Springs Vineyard and Brewery