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Holiday Rentals in Windsor and Maidenhead
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Our top choices for Windsor and Maidenhead holiday rentals
The price is €158
includes taxes & fees
4 Jan - 5 Jan 2026

Spacious, light apartment sleeps up to four
Spacious, light apartment sleeps up to fourCookham
9.8 out of 10, Exceptional, (18)
The price is €246
includes taxes & fees
28 Dec - 29 Dec

A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.Old Windsor
9.6 out of 10, Exceptional, (4)
The price is €152
includes taxes & fees
1 Jan - 2 Jan 2026

9.8 out of 10, Exceptional, (13)

SnoozeDen Westmead| Double Room
SnoozeDen Westmead| Double RoomClewer East
The price is €69
includes taxes & fees
4 Jan - 5 Jan 2026

Stylish 2Bed/2Bath Flat In The Heart Of Windsor
Stylish 2Bed/2Bath Flat In The Heart Of WindsorWindsor City Centre
10.0 out of 10, Exceptional, (5)
The price is €305
includes taxes & fees
5 Jan - 6 Jan 2026

9.0 out of 10, Wonderful, (25)
The price is €245
includes taxes & fees
2 Jan - 3 Jan 2026

Maygrove Retreat - Sleeps 2 - Jacuzzi - Parking
Maygrove Retreat - Sleeps 2 - Jacuzzi - ParkingWraysbury
10.0 out of 10, Exceptional, (1)
The price is €297
includes taxes & fees
23 Jan - 24 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Top Windsor and Maidenhead Hotel Reviews

Sir Christopher Wren Hotel
10/10 Excellent
Find out more about Windsor and Maidenhead
Holiday Homes in Windsor and Maidenhead
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