
Vacation rentals with a pool in Wintergreen Resort
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Wintergreen Resort
Guests agree: these homes with a pool 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 rentals with a pool
House rentals with a pool

Luxury|Hot Tub|Sauna|Cold Plunge|Game Room|Views

Lily Pad - 5 Br/4 Ba Wintergreen Family Retreat

Cottage on the Knoll ~ Prvt Pool & Hot Tub OPEN

Farmhouse on Working Vineyard

Casa Perfecta

Hot Tub EV Charger Mntn View Fireplace Grill Pool

Bear's Mountain Escape

Misty Mountain Cabin w/spa
Condo rentals with a pool

On the mountain, pet and child friendly

Wintergreen! Dog friendly, cozy and comfortable

Wintergreen Mountain Views - Diamond in the Slopes

Recently updated - view of the Blue Ridge Mtns

Nature’s Haven 1 Bedroom Condo Wintergreen Resort

Time To Get Away-Cozy Condo for 2 to 4

Love of mountains oh fill my cup

Happy hour on the 18th Hole
Other vacation rentals with a pool

Stunning Views, Hot Tub, Impeccable Design

Hot Tub! Wintergreen Resort!

Mountain View Charm

Luxury Condo: Stunning Slope Views, Sauna, Dogs-Ok

Luxury|Outdoor Lounge|Hot Tub|Fire Pit|Family&Pets

Luxury House on Mountain Golf Course: Book Summer

Cozy 3BR/2BR+Fire table+Foosball

Stunning Views | Hot Tub | Walk to Ski Slopes
Quick stats about vacation rentals with a pool in Wintergreen Resort
Total rentals
410 properties
Nightly prices starting at
$96 CAD before taxes and fees
Total number of reviews
14K reviews
Family-friendly rentals
310 properties are a good fit for families
Pet-friendly rentals
140 properties allow pets
Rentals with dedicated workspaces
140 properties have a dedicated workspace
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- House rentals Wintergreen Resort
- Rentals with outdoor seating Wintergreen Resort
- Rentals with a firepit Wintergreen Resort
- Ski-in/ski-out rentals Wintergreen Resort
- Rentals with a patio Wintergreen Resort
- Rentals with a hot tub Wintergreen Resort
- Pet-friendly rentals Wintergreen Resort
- Family-friendly rentals Wintergreen Resort
- Rentals with a fireplace Wintergreen Resort
- Rentals with a washer and dryer Wintergreen Resort
- Condo rentals Wintergreen Resort
- Rentals with an EV charger Wintergreen Resort
- Rentals with lake access Wintergreen Resort
- Apartment rentals Wintergreen Resort
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- Cabin rentals Wintergreen Resort
- Rentals with pools Nelson County
- Rentals with pools Virginia
- Rentals with pools United States
- Massanutten Resort
- Omni Homestead Resort
- Early Mountain Winery
- Boonsboro Country Club
- Ash Lawn-Highland
- Amazement Square
- Homestead Ski Slopes
- Chisholm Vineyards at Adventure Farm
- Frontier Culture Museum
- Massanutten Ski Resort
- Liberty Mountain Snowflex Centre
- The Plunge Snow Tubing Park
- Wintergreen Resort
- Spring Creek Golf Club
- Cardinal Point Winery
- Meriwether Springs Vineyard and Brewery
- Blenheim Vineyards
- Farmington Country Club
- Birdwood Golf Course
- Burnley Vineyards
- Glass House Winery