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Old Windsor holiday rentals
We found 31 holiday rentals — enter your dates for availability
Discover a selection of 6 homes and other holiday rentals in Old Windsor that are perfect for your trip. Whether you're going on holiday with family or friends, holiday rentals have the best amenities for spending time at your holiday home, such as air conditioning and Wi-Fi. At the end of the day, you're sure to find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
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Find the best place to stay - Old Windsor

A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
Sleeps 5 · 2 bedrooms · 1 bathroom
9.4 out of 10
exceptional
(3 reviews)
Top rated rentals - Old Windsor

Perfect
10 out of 10
exceptional
(17 reviews)
Absolutely fabulous location. Very close to restaurants, a small supermarket and local pub. Cosey cottage behind the main house with a country feel and quiet backyard. Hosts were amazing and went above and beyond to help with every need.
Andrea L.
Stayed May 2025
- Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value