Montgomery is a town in Orange County, New York, United States. The population was 22,606 at the 2010 census. It was named in honor of Richard Montgomery, an American Revolutionary War general killed in 1775 at the Battle of Quebec.

The Town of Montgomery is in the northern part of the county at the county line shared by Ulster County. Montgomery is immediately west of the Town of Newburgh. It contains three villages, one also called Montgomery, as well as Walden and most of Maybrook.

Town of Crawford rentals with pool

We found 46 rentals with pool — enter your dates for availability

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December 2025

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January 2026

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Showing deals for: 6 Mar - 9 Mar

Living area

Beautiful house with expansive deck, fire pits, hot tub and 240V EV charger

Sleeps 12 · 5 bedrooms · 2+ bathrooms

for 3 nights, 1 home

NZ$1,548 per night

includes taxes & fees

Exterior

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Esopus Escape: Secluded Escape with Hot Tub & Fireplace

Sleeps 8 · 2 bedrooms · 3 bathrooms

for 3 nights, 1 home

NZ$916 per night

includes taxes & fees

Exterior

Premier Host

Modern Hudson Valley Oasis - 1.5hrs from NYC with heated pool, hot tub, sauna!

Sleeps 16 · 6 bedrooms · 3+ bathrooms

for 3 nights, 1 home

NZ$2,451 per night

includes taxes & fees

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Rentals with Pool in Town of Crawford

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