Middlesex County rentals with pool

We found 369 rentals with pool — enter your dates for availability

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November 2025

December 2025

Explore Middlesex County rentals with pools

Room

Charming Groton Farmhouse Apartment

Sleeps 99 · 1 bedroom · 1 bathroom

Exterior

Well-Maintained Property in a Quiet, Tree-Lined Neighborhood. Ideal Location.

Sleeps 8 · 3 bedrooms · 1+ bathroom

Pool

Premier Host

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

Sleeps 13 · 5 bedrooms · 5+ bathrooms

Lake

Premier Host

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

Sleeps 8 · 4 bedrooms · 4+ bathrooms

Exterior

Premier Host

Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym!

Sleeps 14 · 6 bedrooms · 4 bathrooms

Find spaces that suit your style

House

Condo/Apartment

Holiday Rental options in Middlesex County

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Ski holiday rentals in Middlesex County

Mountain holiday rentals in Middlesex County

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