Dutchess County family rentals

We found 1,357 family rentals — enter your dates for availability

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October 2025

November 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

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

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

Sleeps 12 · 8 bedrooms · 5+ bathrooms

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Holiday Rental options in Dutchess County

Pet-friendly holiday rentals in Dutchess County

Monthly rentals in Dutchess County

Holiday rentals with spa pool in Dutchess County

Ski holiday rentals in Dutchess County

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Beach holiday rentals in Dutchess County

Holiday rentals with pool in Dutchess County

Oceanfront holiday rentals in Dutchess County

Mountain holiday rentals in Dutchess County

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