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Holiday Rentals in Windsor and Maidenhead
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Our top choices for Windsor and Maidenhead holiday rentals
10.0 out of 10, Exceptional, (199)
"Wonderful place ideal for families "
Zoe
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)
"Beautifully refurbished property with very helpful hosts."
Alexandra C.
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)
"Had a great stay prior to our flight home. They had everything we needed including things for the kids (1 and 3)."
Peyton T.
The price is €152
includes taxes & fees
1 Jan - 2 Jan 2026
9.8 out of 10, Exceptional, (13)
"What an absolutely stunning apartment in a perfect location to explore Windsor.
Spotlessly clean with everything you could possibly need for a few nights away. Even a Christmas tree which was a lovely surprise.
Once we had a direct contact number for the property the communication was fantastic with check in details and instructions provided.
Would 100% stay again in the future
Thankyou "
Corinne
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)
"We had a wonderful time in Windsor and really enjoyed this place! It was even cuter in person! The location was amazing and space was amazing. "
Natasha C.
The price is €305
includes taxes & fees
5 Jan - 6 Jan 2026
9.0 out of 10, Wonderful, (25)
"Brilliant location and very helpful owner "
Senan
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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