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New Windsor rentals with pool

We found 153 rentals with pool — enter your dates for availability

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August 2025

28

September 2025

Explore New Windsor rentals with pools

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Woodland Sanctuary - 6000ft retreat for pure relaxation!

Sleeps 18 · 7 bedrooms · 5 bathrooms

Patio off kitchen side door with three seating areas.

Beacon Retreat with Hudson River views and access to hiking trails and downtown!

Sleeps 12 · 6 bedrooms · 3+ bathrooms

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