Where will you be on 19 May 2018?

In Windsor Castle, attending the wedding of Prince Harry and Meghan Markle?

Or maybe in Wembley watching the FA Cup final?

Windsor and Maidenhead rentals with pool

We found 36 rentals with pool — enter your dates for availability

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December 2025

January 2026

Explore Windsor and Maidenhead rentals with pools

Premier Host

Luxury Stay w/ Pool, Hot Tub, Gym & Garden

Sleeps 12 · 5 bedrooms · 7+ bathrooms

ON Thames river! Unique home w/amazing Windsor Castle views & excellent location

Sleeps 6 · 3 bedrooms · 3+ bathrooms

Top rated rentals with pools - Windsor and Maidenhead

Wonderful

Loved staying at Lesley’s beautiful gatehouse. It had everything we needed and was very comfortable. Lesley made us feel very welcome. Perfect.

Carole W.

Stayed Sept 2024

Great location, beautiful view, very nice property

Couldn't have had a better experience or been in a nicer place. Expensive but worth it. House right across the river from Windsor Castle. Three levels with three nice bedrooms/ensuites. All the supplies and needed household items on site when we arrived.

david b.

Stayed Aug 2022

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Rentals with Pool in Windsor and Maidenhead

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