Killington featuring autumn leaves and golf

Rutland County ski-in/ski-out rentals

We found 518 ski-in/ski-out rentals — enter your dates for availability

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September 2025

15

October 2025

Find the best place to stay - Rutland County

Breathtaking , relaxing and private haven. Perfect for unwinding from busy life

Premier Host

Ultimate relaxing vacation

Sleeps 6 · 3 bedrooms · 1+ bathroom

Front west facing door of main house.

Premier Host

Historic Home w/glass house, mtn views, swim pond, near skiing, weekly discounts

Sleeps 7 · 4 bedrooms · 3 bathrooms

Exterior

Premier Host

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

Sleeps 10 · 4 bedrooms · 3+ bathrooms

Living area

Premier Host

Pico F305 Ski right to the lifts at Pico Vaulted ceilings Light and Bright. (please note this unit has NO AIR CONDITIONING)

Sleeps 8 · 2 bedrooms · 2 bathrooms

Find spaces that suit your style

Holiday Rental options in Rutland County

Family-friendly holiday rentals in Rutland County

Lake holiday rentals in Rutland County

Pet-friendly holiday rentals in Rutland County

Beach holiday rentals in Rutland County

Oceanfront holiday rentals in Rutland County

Holiday rentals with pool in Rutland County

Mountain holiday rentals in Rutland County

Holiday rentals with spa pool in Rutland County

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