Dutchess County ski-in/ski-out rentals

We found 23 ski-in/ski-out rentals — enter your dates for availability

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September 2025

13

October 2025

Find the best place to stay - Dutchess County

Exterior

The Farm at Hyde Park

Sleeps 5 · 2 bedrooms · 1 bathroom

Exterior

Spacious Country Farmhouse on 8 Lush Acres, Five Minutes to Rhinebeck Village

Sleeps 10 · 4 bedrooms · 3+ bathrooms

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Stunning, 8 Bedroom Estate & Retreat. Historic Elegance with Designer Interiors

Sleeps 12 · 8 bedrooms · 5+ bathrooms

Aerial View Private-Luxury 31 Acre Estate.
Catskills Mountains in background.

Premier Host

NEW! Gated 21 Acre Modern Luxury Estate Heated Pool Hot Tub Gym Movie Theater.

Sleeps 20 · 7 bedrooms · 7 bathrooms

Exterior in Spring

Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres

Sleeps 22 · 9 bedrooms · 9+ bathrooms

Exterior

Premier Host

The Lucky Goat, a quiet country cottage about an hour from NYC, just off the TSP

Sleeps 4 · 1 bedroom · 1 bathroom

Find spaces that suit your style

Holiday Rental options in Dutchess County

Family-friendly holiday rentals in Dutchess County

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Monthly rentals in Dutchess County

Beach holiday rentals in Dutchess County

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