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Family Friendly Holidays in Windsor and Maidenhead - Holiday Lettings

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632 family friendly properties

Holiday apartment in Windsor

Windsor apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £195 / night

£1,363 / week

1 / 19

Holiday home in Windsor

Windsor house

2 bedrooms • 1 bathroom • sleeps 4

from £126 / night

£882 / week

1 / 21

Old Windsor holiday cottage rental

Old Windsor cottage

5 bedrooms • 4 bathrooms • sleeps 10

from £630 / night

£4,122 - £6,584 / week

1 / 46

Eton holiday home rental

Eton house

2 bedrooms • 1 bathroom • sleeps 4

from £205 / night

£1,435 / week

1 / 13

Home rental in Sunningdale

Sunningdale house

5 bedrooms • 4 bathrooms • sleeps 12

from £458 / night

£3,206 / week

1 / 16

Maidenhead Riverside holiday cottage rental

Maidenhead Riverside cottage

1 bedroom • 1 bathroom • sleeps 3

from £103 / night

£722 / week

1 / 8

Maidenhead holiday home rental

Maidenhead house

2 bedrooms • 1 bathroom • sleeps 4

from £172 / night

£1,203 / week

1 / 23

Holiday apartment rental

Windsor apartment

2 bedrooms • 3 bathrooms • sleeps 6

from £258 / night

£1,804 / week

1 / 4

Apartment rental in Windsor

Windsor apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £138 / night

£962 / week

1 / 18

Apartment rental in Windsor

Windsor apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £241 / night

£1,684 / week

1 / 19

Home rental in Windsor with golf nearby

Windsor house

4 bedrooms • 3 bathrooms • sleeps 7

from £490 / night

£3,424 / week

1 / 54

Holiday apartment with golf nearby in Ascot

Ascot apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £149 / night

£1,043 / week

1 / 11

Windsor holiday apartment rental

Windsor apartment

2 bedrooms • 3 bathrooms • sleeps 4

from £102 / night

£682 / week

1 / 23

Windsor holiday apartment rental

Windsor apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £224 / night

£1,563 / week

1 / 16

Holiday home with golf nearby in Wraysbury

Wraysbury house

4 bedrooms • 3 bathrooms • sleeps 10

from £630 / night

£4,409 / week

1 / 33

Holiday apartment in Windsor

Windsor apartment

2 bedrooms • 1 bathroom • sleeps 4

from £144 / night

£916 - £1,002 / week

1 / 18

Studio rental in Windsor with golf nearby

Windsor studio

Studio • 1 bathroom • sleeps 2

from £92 / night

£642 / week

1 / 12

Eton holiday apartment rental

Eton apartment

2 bedrooms • 1 bathroom • sleeps 5

from £171 / night

£1,195 / week

1 / 23

Holiday studio in Windsor

Windsor studio

Studio • 1 bathroom • sleeps 4

“Wonderful place to stay” Have just stayed here for three nights and would recommend to anybody. It's lovely and has everything you need and a welcome basket is left for you with milk in fridge also. An excellent idea and there is nothing the owners have not thought of. Very friendly and feels like you are at home. Brilliant location. We went to Legoland and its literally ten mins away. We got a taxi into Windsor to see the castle and was only eight pounds which is cheaper than parking. Had a lovely stay and will not hesitate to go back again.

from £260 / night

£1,820 / week

1 / 24

Holiday apartment in Windsor

Windsor apartment

2 bedrooms • 3 bathrooms • sleeps 6

from £224 / night

£1,563 / week

1 / 16

Maidenhead holiday chalet rental

Maidenhead chalet

1 bedroom • 1 bathroom • sleeps 2

from £98 / night

£682 / week

1 / 7

Apartment rental in Maidenhead

Maidenhead apartment

1 bedroom • 1 bathroom • sleeps 3

from £86 / night

£602 / week

1 / 12

Old Windsor holiday cottage rental

Old Windsor cottage

3 bedrooms • 2 bathrooms • sleeps 7

from £390 / night

£2,726 / week

1 / 33

Windsor holiday lodge rental

Windsor lodge

2 bedrooms • 1 bathroom • sleeps 5

from £283 / night

£1,980 / week

1 / 26

Windsor holiday apartment rental

Windsor apartment

1 bedroom • 1 bathroom • sleeps 3

from £103 / night

£610 - £730 / week

1 / 13

Maidenhead holiday apartment rental

Maidenhead apartment

3 bedrooms • 3 bathrooms • sleeps 6

from £195 / night

£1,361 / week

1 / 15

Holiday home with golf nearby in Ascot

Ascot house

5 bedrooms • 3 bathrooms • sleeps 8

from £269 / night

£1,880 / week

1 / 13

Ascot holiday apartment rental

Ascot apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £128 / night

£890 / week

1 / 24

Holiday apartment in Maidenhead

Maidenhead apartment

1 bedroom • 1 bathroom • sleeps 3

from £103 / night

£722 / week

1 / 9

Holiday home rental

Windsor house

4 bedrooms • 3 bathrooms • sleeps 7

from £294 / night

£2,055 / week

1 / 55

Holiday studio in Windsor

Windsor studio

Studio • 1 bathroom • sleeps 4

from £226 / night

£1,579 / week

1 / 21

Holiday home in Old Windsor

Old Windsor house

4 bedrooms • 3 bathrooms • sleeps 7

from £573 / night

£4,008 / week

1 / 51

Holiday apartment letting

Windsor apartment

1 bedroom • 1 bathroom • sleeps 4

from £226 / night

£1,579 / week

1 / 14

Apartment rental in Windsor

Windsor apartment

1 bedroom • 1 bathroom • sleeps 4

from £98 / night

£682 / week

1 / 19

Holiday apartment in Windsor

Windsor apartment

1 bedroom • 1 bathroom • sleeps 2

from £149 / night

£1,042 / week

1 / 53

Holiday apartment in Windsor

Windsor apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £224 / night

£1,563 / week

1 / 26

Holiday home in Knowl Hill

Knowl Hill house

3 bedrooms • 2 bathrooms • sleeps 6

from £287 / night

£2,004 / week

1 / 7

Windsor holiday apartment rental

Windsor apartment

2 bedrooms • 1 bathroom • sleeps 3

from £115 / night

£802 / week

1 / 22

Holiday guest house in Wraysbury

Wraysbury guest house

1 bedroom • 1 bathroom • sleeps 1

from £57 / night

£393 / week

1 / 13

Apartment rental in Windsor

Windsor apartment

2 bedrooms • 1 bathroom • sleeps 4

from £115 / night

£802 / week

1 / 13

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