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Windsor and Maidenhead Holiday Rentals

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    Travellers to Windsor and Maidenhead are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    All 97 Rentals in Windsor and Maidenhead
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    Luxurious Eton / Windsor Thames Riverside getaway!1 / 26
    (22)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Gorgeous Country Cottage, beside Windsor Great Park & overlooking Windsor Castle1 / 47
    (61)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Quintessential english cottage perfect for ' The Season' events & fine dining1 / 19
    (31)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Old Windsor, Windsor SL4 2HL
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    Ascot, Windsor and Maidenhead SL5 9JL
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
    Lovely Flat With Parking In The Centre Of Royal Windsor1 / 19
    (9)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Windsor, Windsor and Maidenhead SL4 2AG
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    RIVERSIDE, ROYAL WINDSOR, LONDON /LEGOLAND WITHIN 20 MINS, FREE WI-FI/PARKING1 / 49
    (30)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Windsor, Windsor and Maidenhead SL4 2JY
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    First floor apartment in the heart of Windsor, next door to the Castle.1 / 13
    (26)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Windsor, Windsor and Maidenhead SL4 1PE
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 7
    Stunning Eton Apartment1 / 33
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Eton, Windsor SL4 6AS
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Stylish & Spacious 5 bedroom town house in Central Windsor1 / 36
    (7)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    Windsor, Windsor and Maidenhead SL4 3AX
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location Information
    Fifield, Windsor and Maidenhead SL4 4PZ
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    5 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    Cookham, Windsor and Maidenhead SL6
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 14
    ROYAL WINDSOR, RIVERSIDE, WI-FI, 4 BEDROOM FAMILY HOME,3 BATH, SLEEPS UPTO 71 / 50
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Location Information
    Windsor, Windsor and Maidenhead SL42JY
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Riverside Bungalow near legoland, Windsor, Hot Tub & Sauna. Pet Friendly.1 / 27
    (52)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Wraysbury, Windsor and Maidenhead TW19 5EY
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Homely flat with castle view and parking1 / 25
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Windsor, Windsor and Maidenhead SL4 5BY
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Wraysbury, Windsor and Maidenhead TW19 5EN
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windsor, Windsor and Maidenhead SL4 3AA
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Fifield, Windsor and Maidenhead SL44PZ
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Windsor, Windsor and Maidenhead SL4 1LD
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Ascot, Windsor and Maidenhead SL5 7DY
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    THE OLD SCHOOL HOUSE, ASCOT, BERKSHIRE1 / 21
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Ascot, Windsor and Maidenhead SL5 7QR
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    LEGOLAND, RIVER SIDE, WEST LONDON, ROYAL WINDSOR, free WIFI & PARKING, Sleeps 71 / 50
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Old Windsor, Windsor SL4 2JY
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Maidenhead, Windsor and Maidenhead SL6
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
    Spacious Comfy 2 bed 1 bath apartment1 / 23
    (3)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Ascot, Windsor and Maidenhead SL5 8NF
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Maidenhead house near Legoland, Windsor & Heathrow, 20 mins to London - sleeps 41 / 24
    (6)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Maidenhead, Windsor and Maidenhead SL66LG
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Windsor, Windsor and Maidenhead SL4 1LU
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Old Windsor, Windsor SL4 2JY
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windsor, Windsor and Maidenhead SL4
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Victorian Apartment in the Heart of Windsor1 / 10
    (9)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Windsor, Windsor and Maidenhead SL4 3BZ
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windsor, Windsor and Maidenhead SL4 1PL
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Gardner's Cottage Sister property1 / 36
    (2)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Windsor, Windsor and Maidenhead SL41SJ
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windsor, Windsor and Maidenhead SL4 1PR
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Maidenhead, Windsor and Maidenhead SL6 8AZ
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Windsor, Windsor and Maidenhead SL4 6AB
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windsor, Windsor and Maidenhead SL4 4WA
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    Windsor, Windsor and Maidenhead SL4 3DL
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 5
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Maidenhead, Windsor and Maidenhead SL6 1AW
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Wraysbury, Windsor and Maidenhead TW19 6HG
    Condo/Apartment - 4 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windsor, Windsor and Maidenhead SL4 1LD
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Windsor, Windsor and Maidenhead SL4 5JS
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 8
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Wraysbury, Windsor and Maidenhead TW19 5AG
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 2
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windsor, Windsor and Maidenhead SL4 1BG
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    Wraysbury, Windsor and Maidenhead TW19 6HG
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 2
    1 Bedroom, 1 Bathroom, Sleeps 1 Quick View
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    Maidenhead, Windsor and Maidenhead SL6
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 1
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Maidenhead, Windsor and Maidenhead SL6 8FF
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    The Maple, Legoland and Windsor Apartments1 / 17
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Windsor, Windsor and Maidenhead SL4 3EE
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Period Cottage in the center of Windsor1 / 43
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Windsor, Windsor and Maidenhead SL4 1EU
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Windsor, Windsor and Maidenhead SL4 1PL
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Old Windsor, Windsor SL4 2JY
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    NEW - Fabulous location for families, converted stables, 5 mins to Legoland1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Washer
    • Parking
    • Central Heating
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Windsor, Windsor and Maidenhead SL4 4PZ
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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