Killington featuring autumn leaves and golf

Rutland County rentals with pool

We found 778 rentals with pool — enter your dates for availability

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Dates

Calendar
Flexible dates

September 2025

15

October 2025

Explore Rutland County rentals with pools

Room

Premier Host

Great King Bed studio, close to lifts, spa, indoor pool and great restaurants!

Sleeps 2 · 1 bathroom

Exterior

Premier Host

Views!-Spacious 3-floor Custom Chalet. 18 acres. Ski most resorts within an hour

Sleeps 12 · 3 bedrooms · 3 bathrooms

Exterior detail

Premier Host

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Sleeps 16 · 7 bedrooms · 4+ bathrooms

Family Room and Balcony

Premier Host

SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside

Sleeps 8 · 3 bedrooms · 2 bathrooms

one of a kind fully updated lofted ceiling real wood fireplace end unit

Luxury Trail Creek ski home 2king & 4twin beds sauna hot tub end unit internet

Sleeps 8 · 3 bedrooms · 3+ bathrooms

Find spaces that suit your style

Holiday Rental options in Rutland County

Family-friendly holiday rentals in Rutland County

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Mountain holiday rentals in Rutland County

Holiday rentals with spa pool in Rutland County

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