One of my favorite old 1800s covered bridges I got to enjoy today was the silk bridge. You can still travel on it but it is only wide enough for one car at a time. A beautiful piece of history in Bennington, VT

Bennington County rentals with pool

We found 534 rentals with pool — enter your dates for availability

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December 2025

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January 2026

Explore Bennington County rentals with pools

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Premier Host

Beautiful Lakeview Log Cabin on 60-Acre Property

Sleeps 24 · 9 bedrooms · 7 bathrooms

The 30' lap pool is right outside your door.

Premier Host

FARM-TO-TABLE eating, good hot tub soak, S'mores around fire pit, seasonal POOL!

Sleeps 6 · 1 bedroom · 1 bathroom

Skating Pond in front of building & Mill House (serving hot drinks, sandwiches)

Premier Host

Spacious 4Br/4Bth Lodge With Ice Skating Pond, Heated Pool, 3 Min Walk To Ski

Sleeps 10 · 4 bedrooms · 4 bathrooms

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Rentals with Pool in Bennington County

Holiday Rental options in Bennington County

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