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Pawling family rentals

We found 246 family rentals — enter your dates for availability

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November 2025

December 2025

Find the best place to stay - Pawling

Showing deals for: 2 Feb - 5 Feb

Harlem Valley Hideout: Artsy ~ Pool ~ Tennis

Sleeps 6 · 3 bedrooms · 3+ bathrooms

for 3 nights, 1 home

AU$913 per night

includes taxes & fees

"Country outside the city " 3 bedrooms 2 full bathrooms

Sleeps 6 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$627 per night

includes taxes & fees

Premier Host

Woodstove, firepit, lakeviews and access to lake, hiking trails, large terrace!

Sleeps 8 · 4 bedrooms · 3 bathrooms

for 3 nights, 1 cabin

AU$979 per night

includes taxes & fees

Top rated rentals - Pawling

Premier Host

Lovely and homey

Kim and Kevin were super communicative and friendly, and the home was clean and beautifully decorated. The coffee cake was the cherry on top. Perfect for our group! Would absolutely stay again.

Emily H.

Stayed May 2025

Spiral staircase leading to the mezzanine where the bedroom is located.

Cute!

Sitting outside the cottage overlooking the reservoir (on other side of road) was superb after being in hectic New York. The bed was comfy but located up a steep, narrow spiral staircase. Small bathroom downstairs. Eclectic furnishings. Very clean. Would recommend seniors opt for house option rather than cottage. Host very pleasant.

Deborah W.

Stayed Sept 2024

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