Town of Highlands rentals with pool

We found 53 rentals with pool — enter your dates for availability

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November 2025

December 2025

Explore Town of Highlands rentals with pools

Showing deals for: 30 Jan - 2 Feb

Private lake escape

Sleeps 4 · 3 bedrooms · 1 bathroom

for 3 nights, 1 home

NZ$903 per night

includes taxes & fees

Charming Cottage conveniently located in serene Tomkins Cove

Sleeps 4 · 1 bedroom · 1 bathroom

for 3 nights, 1 cottage

NZ$882 per night

includes taxes & fees

The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC

Sleeps 10 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

NZ$1,503 per night

includes taxes & fees

Premier Host

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

Sleeps 12 · 5 bedrooms · 4 bathrooms

for 3 nights, 1 villa

NZ$1,755 per night

includes taxes & fees

Find spaces that suit your style

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Explore Town of Highlands rentals with pools

Private lake escape

Cold Spring Village Maisonette with Pool

Cozy House on the hill

Charming Cottage conveniently located in serene Tomkins Cove

The Hudson Hideaway! Pool, Hot Tub, Sauna ~1HR to NYC

Spacious + beautiful 5-bedroom Mediterranean Villa in Monroe, NY.

Find spaces that suit your style

Rentals with Pool in Town of Highlands

Holiday Rental options in Town of Highlands