Photo by Melissa Smestad
Holiday Rentals in Wintergreen
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Our top choices for Wintergreen holiday rentals

Laurelwood Hollow: Walk to Ski & Swim
Laurelwood Hollow: Walk to Ski & SwimWintergreen Resort
10.0 out of 10, Exceptional, (2)
The price is €241
includes taxes & fees
13 Jan - 14 Jan 2026

First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodge
First Floor Slopeside Ski-in / Ski-out at Wintergreen, steps from main lodgeWintergreen Resort
10.0 out of 10, Exceptional, (2)
The price is €228
includes taxes & fees
21 Jan - 22 Jan 2026

The Modern Mountain Condo
The Modern Mountain CondoWintergreen Resort
10.0 out of 10, Exceptional, (36)
The price is €241
includes taxes & fees
13 Jan - 14 Jan 2026

Wintergreen. Sunset Vista Villa - Close to the ski slopes
Wintergreen. Sunset Vista Villa - Close to the ski slopesWintergreen Resort
10.0 out of 10, Exceptional, (94)
The price is €302
includes taxes & fees
12 Jan - 13 Jan 2026

Pine Cottage: Hot Tub, 2 mins to Bold Rock!
Pine Cottage: Hot Tub, 2 mins to Bold Rock!Nellysford
10.0 out of 10, Exceptional, (23)
The price is €402
includes taxes & fees
14 Jan - 15 Jan 2026

Retreat @ 3 Ridges / 3 min walk -> Slopes & Dining
Retreat @ 3 Ridges / 3 min walk -> Slopes & DiningWintergreen Resort
10.0 out of 10, Exceptional, (24)
The price is €322
includes taxes & fees
13 Jan - 14 Jan 2026

Cozy studio in the fantastic Wintergreen Resort, Ski-in, ski-out. First floor,
Cozy studio in the fantastic Wintergreen Resort, Ski-in, ski-out. First floor,Wintergreen Resort
The price is €298
includes taxes & fees
4 Jan - 5 Jan 2026

New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendly
New construction! 1 BD/2 BA Top of Wintergreen mountain. Sleeps 4, pet-friendlyRoseland
9.6 out of 10, Exceptional, (142)
The price is €231
includes taxes & fees
5 Jan - 6 Jan 2026








































































