Apartments in Windsor and Maidenhead and Houses – Holiday Lettings - Holiday Rentals Windsor and Maidenhead

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1,115 Holiday homes

(8) Excellent 

5

Holiday home in Eton

Windsor / Eton

3 8 2 nights min

  • 3 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly

from £344 / night

£2,290 / week

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from £344 / night

(3) Excellent 

22

Eton holiday home rental

Windsor / Eton

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Private garden

from £148 / night

£1,034 / week

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from £148 / night

(2) Excellent 

12

Holiday apartment rental

Windsor and Maidenhead / Windsor

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Child friendly

from £114 / night

£794 / week

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Responds fast!
avg. 2 hours 20 minutes

from £114 / night

16

Home rental in Sunningdale

Windsor and Maidenhead / Sunningdale

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 110 km
  • Child friendly
  • Pet friendly

from £401 / night

£2,384 / week

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Responds fast!
avg. 21 minutes

from £401 / night

(15) Very Good 

26

Eton holiday home rental

Windsor / Eton

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Private garden

from £172 / night

£1,203 / week

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Responds fast!
avg. 2 hours 28 minutes

from £172 / night

(1) Very Good 

16

Holiday home in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden

from £126 / night

£762 - £831 / week

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Responds fast!
avg. 2 hours 25 minutes

from £126 / night

18

Windsor holiday apartment rental

Windsor and Maidenhead / Windsor

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Child friendly

from £109 / night

£745 / week

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Responds fast!
avg. 2 hours 25 minutes

from £109 / night

(2) Very Good 

19

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child friendly
  • Car not necessary

from £150 / night

£1,048 / week

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Responds fast!
avg. 2 hours 25 minutes

from £150 / night

(1) Excellent 

19

Apartment rental in Windsor

Windsor and Maidenhead / Windsor

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly

from £241 / night

£1,684 / week

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from £241 / night

13

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Child friendly

from £207 / night

£1,443 / week

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from £207 / night

23

Maidenhead holiday home rental

Windsor and Maidenhead / Maidenhead

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £144 / night

£1,002 / week

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Responds fast!
avg. 1 hour 27 minutes

from £144 / night

(1) Excellent 

8

Maidenhead Riverside holiday cottage rental

Maidenhead / Maidenhead Riverside

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Child friendly
  • Pet friendly

from £86 / night

£602 - £722 / week

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from £86 / night

(1) Excellent 

4

Holiday apartment rental

Windsor and Maidenhead / Windsor

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly

from £224 / night

£1,563 / week

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from £224 / night

5

Holiday home in Eton

Windsor / Eton

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly

from £287 / night

£1,718 / week

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from £287 / night

(19) Excellent 

23

Holiday home in Windsor

Windsor and Maidenhead / Windsor

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Private garden

from £172 / night

£1,203 / week

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Responds fast!
avg. 2 hours 28 minutes

from £172 / night

(1) Excellent 

38

Home rental in Maidenhead

Windsor and Maidenhead / Maidenhead

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £115 / night

£802 / week

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Responds fast!
avg. 1 hour 27 minutes

from £115 / night

(8) Very Good 

37

Holiday cottage rental

Windsor / Old Windsor

4 12 2 nights min

  • 4 bedrooms
  • sleeps 12
  • 2 nights min
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

from £687 / night

£2,863 - £6,458 / week

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from £687 / night

24

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child friendly

from £194 / night

£1,355 / week

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from £194 / night

(1) Excellent 

43

Home rental in Windsor with golf nearby

Windsor and Maidenhead / Windsor

4 7 min stay varies

  • 4 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

from £186 / night

£1,260 - £2,404 / week

Book View

Responds fast!
avg. 1 hour 28 minutes

from £186 / night

11

Apartment rental in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly

from £126 / night

£745 - £802 / week

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Responds fast!
avg. 2 hours 25 minutes

from £126 / night

5

Holiday studio in Maidenhead

Windsor and Maidenhead / Maidenhead

Studio 2 1 night min

  • Studio
  • sleeps 2
  • 1 night min
  • Child friendly
  • Private garden

from £78 / night

£474 - £694 / week

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from £78 / night

(3) Excellent 

7

Holiday apartment with golf nearby in Ascot

Windsor and Maidenhead / Ascot

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 85 km
  • Child friendly

from £120 / night

£835 / week

Enquire View

from £120 / night

(30) Very Good 

Certificate of Excellence

17

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Car not necessary

Certificate of Excellence

from £121 / night

£550 - £722 / week

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Responds fast!
avg. 2 hours 40 minutes

from £121 / night

(2) Excellent 

11

Holiday apartment with golf nearby in Ascot

Windsor and Maidenhead / Ascot

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child friendly

from £125 / night

£875 / week

Enquire View

from £125 / night

23

Windsor holiday apartment rental

Windsor and Maidenhead / Windsor

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Car not necessary

from £102 / night

£682 - £1,203 / week

Book View

from £102 / night

16

Windsor holiday apartment rental

Windsor and Maidenhead / Windsor

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Child friendly

from £224 / night

£1,563 / week

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from £224 / night

(3) Excellent 

30

Studio rental in Old Windsor

Windsor / Old Windsor

Studio 4 min stay varies

  • Studio
  • sleeps 4
  • min stay varies
  • Private garden

from £172 / night

£1,203 / week

Book View

from £172 / night

(6) Very Good 

12

Studio rental in Windsor with golf nearby

Windsor and Maidenhead / Windsor

Studio 2 4 nights min

  • Studio
  • sleeps 2
  • 4 nights min
  • Child friendly
  • Car not necessary
  • Private garden

from £86 / night

£602 / week

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Responds fast!
avg. 2 hours 4 minutes

from £86 / night

(2) Excellent 

12

Holiday b&b rental

Windsor and Maidenhead / Windsor

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min

from £115 / night

£802 / week

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Responds fast!
avg. 3 hours 21 minutes

from £115 / night

(3) Excellent 

33

Holiday home with golf nearby in Wraysbury

Windsor and Maidenhead / Wraysbury

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child friendly

from £275 / night

£1,924 / week

Book View

Responds fast!
avg. 1 hour 39 minutes

from £275 / night

23

Holiday home in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly

from £89 / night

£620 - £820 / week

Enquire View

from £89 / night

16

Holiday apartment rental

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Suitable for children age 5+
  • Car not necessary

from £138 / night

£882 / week

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Responds fast!
avg. 2 hours 25 minutes

from £138 / night

12

Home rental in Datchet

Windsor and Maidenhead / Datchet

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Child friendly

from £70 / night

£485 / week

Enquire View

from £70 / night

(1) Excellent 

12

Apartment rental in Maidenhead

Windsor and Maidenhead / Maidenhead

1 3 5 nights min

  • 1 bedroom
  • sleeps 3
  • 5 nights min
  • Child friendly
  • Car not necessary

from £86 / night

£602 / week

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Responds fast!
avg. 29 minutes

from £86 / night

6

Maidenhead holiday chalet rental

Windsor and Maidenhead / Maidenhead

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Child friendly
  • Pet friendly

from £69 / night

£481 - £602 / week

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from £69 / night

(6) Excellent 

33

Old Windsor holiday cottage rental

Windsor / Old Windsor

3 7 3 nights min

  • 3 bedrooms
  • sleeps 7
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Pet friendly

from £218 / night

£1,523 / week

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from £218 / night

(16) Excellent 

Certificate of Excellence

23

Eton holiday apartment rental

Windsor / Eton

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary

Certificate of Excellence

from £171 / night

£1,195 / week

Book View

Responds fast!
avg. 3 hours 45 minutes

from £171 / night

(8) Very Good 

18

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary

from £103 / night

£710 - £939 / week

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Responds fast!
avg. 2 hours 4 minutes

from £103 / night

(3) Very Good 

14

Old Windsor holiday studio rental

Windsor / Old Windsor

Studio 3 1 night min

  • Studio
  • sleeps 3
  • 1 night min
  • Child friendly
  • Car not necessary

from £126 / night

£882 / week

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Responds fast!
avg. 1 hour 17 minutes

from £126 / night

34

Holiday townhouse in Windsor

Windsor and Maidenhead / Windsor

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary

from £147 / night

£1,026 / week

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from £147 / night

Top Destination reviews

The Loft Windsor
Excellent location

Beautiful flat, excellent location, plenty of cupboards in bedroom for cases etc. 10 minute walk from centre. Very helpful owner. flat very clean and comfortable. We wont look for anywhere else to stay if we visit Windsor again. … see more
9 The Courtyard, Windsor
Easter family break

Great flat for a family of four, just off Windsor high street. Perfect apart from slight smell of cigarette smoke, perhaps from previous occupants and two floors up, so perhaps not suitable for young children. However, suited our needs. Would definately stay again. … see more
Eton/Windsor
Immaculate cottage in a perfect location

The cottage was immaculately clean and beautifully presented. Excellent attention to detail, with a lovely welcome hamper and more than enough towels. The location is just perfect. In a secluded pretty lane just of Eton high street which is lovely and quiet. Yet less than 5 minutes walk from Windsor, the castle, the river, and all the bars, cafes and restaurants you could want. I would definitely return and recommend it as a place for everyone who wants a central location but not noisy! Thank you for a wonderful stay.see more
Duke Street B&B
Outstanding

The Duke Street B&B really is a jewel in the Crown of the Royal Borough, a friendly welcome, excellent facilities, spotlessly clean and the best breakfast in Windsor, Julia certainly takes pride in what she does and made our stay in Windsor even more enjoyable, perfect location with a short walk into town by the river. I would highly reccomend Duke St B&B to anyone visiting Windsorsee more
Beautiful spacious detached family home 10 mins to Legoland
Perfect weekend in Windsor

A brilliant place to stay in windsor, this was such a lucky find at such short notice too! The cottage was clean and beautiful and Justina was very welcoming and accommodating who advised we could check out at a later time if needed. A* we will definitely stay here again Thank you for a great stay Natashasee more
Windsor/Eton 2 Bedroom apartment Central location
Home from Home

Wouldn’t hesitate to recommend this accommodation to anyone wishing to visit Windsor/Eton and or London. Great location, fully equipped, home from home which we would visit again. Owner John is extremely helpful and a pleasure to deal with. Thoroughly enjoyed our trip and our stay at this lovely apartment.see more

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