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

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1,048 Holiday homes

(6) Excellent 

5

Holiday home in Eton

Windsor / Eton

3 8 2 nights min

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

from £300 / night

£2,000 / week

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from £300 / night

(10) Excellent 

15

Apartment rental in Maidenhead Riverside with shared pool

Maidenhead / Maidenhead Riverside

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool

from £53 / night

£365 / week

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from £53 / night

11

Eton holiday home rental

Windsor / Eton

2 4 2 nights min

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

from £149 / night

£1,043 / week

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from £149 / night

(12) Very Good 

25

Old Windsor holiday cottage rental

Windsor / Old Windsor

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

from £500 / night

£2,800 / week

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from £500 / night

(2) Excellent 

12

Holiday apartment rental

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly

from £129 / night

£903 / week

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Responds fast!
avg. 2 hours 20 minutes

from £129 / night

5

Holiday home in Eton

Windsor / Eton

2 6 2 nights min

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

from £250 / night

£1,500 / week

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from £250 / night

(29) 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 £105 / night

£480 - £630 / week

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Responds fast!
avg. 2 hours 27 minutes

from £105 / 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 £149 / night

£1,043 / week

Book View

Responds fast!
avg. 3 hours 0 minutes

from £149 / night

(44) Excellent 

Certificate of Excellence

27

Holiday cottage in Windsor

Windsor and Maidenhead / Windsor

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Private garden

Certificate of Excellence

from £135 / night

£945 / week

Book View

Responds fast!
avg. 45 minutes

from £135 / 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 £75 / night

£525 / week

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Responds fast!
avg. 3 hours 25 minutes

from £75 / 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 £125 / night

£875 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £125 / 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 £195 / night

£1,365 / week

Book View

from £195 / night

19

Apartment rental in Windsor

Windsor and Maidenhead / Windsor

2 6 2 nights min

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

from £210 / night

£1,470 / week

Book View

from £210 / 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 £75 / night

£525 - £650 / week

Book View

from £75 / 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 £131 / night

£915 / week

Book View

Responds fast!
avg. 2 hours 40 minutes

from £131 / 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 £350 / night

£2,082 / week

Book View

from £350 / 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 £110 / night

£665 - £725 / week

Book View

Responds fast!
avg. 2 hours 40 minutes

from £110 / 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 £100 / night

£700 / week

Book View

Responds fast!
avg. 3 hours 15 minutes

from £100 / night

(2) Excellent 

9

Windsor holiday apartment rental

Windsor and Maidenhead / Windsor

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Suitable for children age 5+

from £75 / night

£525 / week

Book View

Responds fast!
avg. 2 hours 38 minutes

from £75 / night

(1) Excellent 

16

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

2 6 2 nights min

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

from £195 / night

£1,365 / week

Book View

from £195 / 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 £110 / night

£770 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £110 / 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 £180 / night

£1,260 / week

Book View

from £180 / night

21

Holiday home in Sunninghill

Ascot / Sunninghill

4 9 2 nights min

  • 4 bedrooms
  • sleeps 9
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

from £895 / night

£7,000 / week

Book View

Responds fast!
avg. 2 hours 55 minutes

from £895 / night

(2) Excellent 

26

Studio rental in Old Windsor

Windsor / Old Windsor

Studio 4 min stay varies

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

from £148 / night

£1,036 / week

Book View

from £148 / night

39

Maidenhead holiday apartment rental

Windsor and Maidenhead / Maidenhead

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Child friendly

from £140 / night

£980 / week

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from £140 / night

(16) Excellent 

18

Holiday cottage in Holyport

Windsor and Maidenhead / Holyport

2 4 2 nights min

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

from £105 / night

£735 / week

Book View

from £105 / night

(12) Excellent 

21

Holiday studio in Windsor

Windsor and Maidenhead / Windsor

Studio 4 2 nights min

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

from £175 / night

£1,225 / week

Book View

Responds fast!
avg. 1 hour 8 minutes

from £175 / night

(12) Excellent 

Certificate of Excellence

14

Windsor holiday home rental

Windsor and Maidenhead / Windsor

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

Certificate of Excellence

from £270 / night

£1,875 - £2,000 / week

Book View

Responds fast!
avg. 1 hour 44 minutes

from £270 / 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 £68 / night

£414 - £606 / week

Book View

from £68 / night

(41) Excellent 

22

Holiday studio in Windsor

Windsor and Maidenhead / Windsor

Studio 4 2 nights min

  • Studio
  • sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
“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 £185 / night

£1,295 / week

Book View

Responds fast!
avg. 1 hour 8 minutes

from £185 / night

(3) Excellent 

4

Home rental in Eton

Windsor / Eton

4 6 min stay varies

  • 4 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Car not necessary
  • Private garden

from £550 / night

£3,850 / week

Book View

from £550 / night

(7) 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 £85 / night

£595 - £820 / week

Book View

Responds fast!
avg. 3 hours 25 minutes

from £85 / night

(11) 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 £175 / night

£1,225 / week

Book View

Responds fast!
avg. 2 hours 28 minutes

from £175 / night

9

Home rental in Windsor

Windsor and Maidenhead / Windsor

5 8 2 nights min

  • 5 bedrooms
  • sleeps 8
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £295 / night

£2,065 / week

Book View

Responds fast!
avg. 2 hours 5 minutes

from £295 / night

(32) Excellent 

Certificate of Excellence

22

Holiday home in Windsor

Windsor and Maidenhead / Windsor

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Private garden
“Beautiful cottage” We enjoyed our stay so much we would like to have stayed longer. Beautiful inside and out with lots of extras not found in holiday rentals. Warm and comfortable. Jill made sure everything was ready for us. The garden would be lovely in summer!

Certificate of Excellence

from £135 / night

£945 / week

Book View

Responds fast!
avg. 45 minutes

from £135 / night

(2) Excellent 

15

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

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

from £115 / night

£700 - £950 / week

Book View

Responds fast!
avg. 2 hours 40 minutes

from £115 / night

(1) Very Good 

9

Apartment rental in Windsor

Windsor and Maidenhead / Windsor

2 4 2 nights min

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

from £155 / night

£700 / week

Book View

Responds fast!
avg. 2 hours 55 minutes

from £155 / 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 £110 / night

£770 / week

Book View

Responds fast!
avg. 1 hour 21 minutes

from £110 / 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 £195 / night

£1,365 / week

Book View

from £195 / night

(7) Excellent 

16

Windsor holiday apartment let

Windsor and Maidenhead / Windsor

2 5 4 nights min

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

from £150 / night

£799 / week

Book View

from £150 / night

Top Destination reviews

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
Self contained 1 bedroomed unit
Lovely

Had a lovely stay here, was nice and tidy, quite spacious and pretty newly furnished. Lesley was very welcoming and gave us all the information we needed about the place and about Windsor. … 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
Pretty contemporary open plan cottage with open fire.
Beautiful cottage

We are just home from a fantastic break at this cottage for 4 nights. The location was perfect, cottage was stunning and ideal for our family of 4. The owner Helen was extremely helpful with any queries we had and the cottage was well equipped for all our needs. We loved that there was a pub next door with a great playpark, our 2 girls loved it. We visited Legoland twice 10 mins in car, close to Windsor and Marlow was stunning. We took the train into London approx an hour. We will definitely be backsee 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