Massachusetts which includes tranquil scenes, forests and autumn colours

Worcester County rentals with pool

We found 74 rentals with pool — enter your dates for availability

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September 2025

14

October 2025

Explore Worcester County rentals with pools

YOUR OWN HEATED POOL

Premier Host

Impressive Unique Waterfront Pool Resort Country Estate

Sleeps 25 · 6 bedrooms · 4 bathrooms

Pool

Premier Host

Private Resort Like Getaway - Close to Wachusett Mountain Ski Resort!

Sleeps 13 · 5 bedrooms · 5+ bathrooms

Castle in the Fall

Premier Host

Unique Luxurious Gothic Castle, gorgeous views of lake/mountain 500 acre estate!

Sleeps 22 · 8 bedrooms · 5+ bathrooms

Lake

Premier Host

Beautiful Private Lakehouse & Infinity Pool Next To Wachusett & Great Wolf Lodge

Sleeps 8 · 4 bedrooms · 4+ bathrooms

Find spaces that suit your style

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Family-friendly holiday rentals in Worcester County

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