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

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Windsor and Maidenhead

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970 Holiday homes

(3) Excellent 

18

Holiday apartment in Maidenhead

Windsor and Maidenhead / Maidenhead

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly

from £115 / night

£770 / week

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from £115 / night

(28) Excellent 

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
“Perfect” Absolutely stunning cottage. Everything you should need. Immensity comfortable beds, lovely furnishings and extremely attentive owners. Perfectly safe garden for children which is gated off from the road. Lovely external seating area and
…see more

from £135 / night

£945 / week

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Responds fast!
avg. 1 hour 46 minutes

from £135 / night

(10) 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
“Gorgeous house on the river” We had a fantastic stay in this lovely house; all the rooms are very large and comfortable, with some great views over the river.
…see more

from £500 / night

£2,800 - £3,500 / week

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from £500 / night

(41) Excellent 

28

Holiday cottage in Windsor

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“Little chauntry” The house is lovely, easily fitted in our family of five as doyble beds as 6 ft each House is very nicely decorated and jill was always prompt in replying to emails
…see more

from £115 / night

£805 / week

Book View

Responds fast!
avg. 1 hour 46 minutes

from £115 / night

36

Studio rental in Old Windsor

Windsor / Old Windsor

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies

from £160 / night

£1,120 / week

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from £160 / 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 - £400 / week

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from £53 / night

(7) Excellent 

8

Holiday home in Cookham

Windsor and Maidenhead / Cookham

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden

from £125 / night

£750 / week

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Responds fast!
avg. 2 hours 52 minutes

from £125 / 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 41 minutes

from £110 / night

(22) 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
“First class” Everything you could hope for, very glad I found it. The owner was most considerate and accommodating.
…see more

Certificate of Excellence

from £105 / night

£480 - £615 / week

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Responds fast!
avg. 1 hour 54 minutes

from £105 / night

13

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Private garden

from £122 / night

£850 / week

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from £122 / night

(15) Excellent 

Certificate of Excellence

26

Windsor holiday lodge rental

Windsor and Maidenhead / Windsor

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Private garden

Certificate of Excellence

from £230 / night

£1,610 / week

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Responds fast!
avg. 1 hour 37 minutes

from £230 / night

(14) Very Good 

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
“An exceptional property. Great location!!!” We had a lovely weeks stay in Eton. Close to Windsor, with a view of the castle. Lovely restaurants on the river, close to trains, shops & cafes. A lovely, romantic stay. A lovely, comfortable bed. Owner lov
…see more

Certificate of Excellence

from £149 / night

£1,043 / week

Book View

Responds fast!
avg. 2 hours 59 minutes

from £149 / night

(8) Excellent 

Certificate of Excellence

26

Eton holiday home rental

Windsor / Eton

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden

Certificate of Excellence

from £175 / night

£1,225 / week

Book View

Responds fast!
avg. 2 hours 44 minutes

from £175 / night

8

Holiday apartment in Maidenhead

Windsor and Maidenhead / Maidenhead

1 2 7 nights min

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

from £75 / night

£525 - £1,250 / week

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from £75 / night

12

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Car not necessary

from £110 / night

£700 - £1,100 / week

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from £110 / night

(1) Very Good 

16

Holiday cottage in Maidenhead Riverside

Maidenhead / Maidenhead Riverside

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly

from £120 / night

£840 - £1,600 / week

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from £120 / night

(14) Excellent 

Certificate of Excellence

21

Holiday home in Windsor

Windsor and Maidenhead / Windsor

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
“Welcoming Hosts” We had a fantastic time over the Christmas period in Windsor. Bridget and her husband were extremely welcoming and friendly. The house was furnished beautifully and cleaned to a very high standard. Thank you for the lovely food hamp
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Certificate of Excellence

from £175 / night

£1,225 / week

Book View

Responds fast!
avg. 2 hours 44 minutes

from £175 / night

12

Holiday apartment rental

Windsor and Maidenhead / Windsor

2 4 7 nights min

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

from £125 / night

£770 - £1,200 / week

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from £125 / night

(2) Excellent 

12

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Car not necessary
“Fantastic apartment. Highly recommend” Thanks to a flexible host, we arrived at the apartment a little earlier than planned. Great comms with host, never waiting very long for a reply to questions asked. Arrival instructions were perfect - no car p
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from £88 / night

£616 / week

Book View

Responds fast!
avg. 2 hours 52 minutes

from £88 / night

(6) Very Good 

Certificate of Excellence

12

Studio rental in Windsor with golf nearby

Windsor and Maidenhead / Windsor

Studio 2 5 nights min

  • Studio
  • Sleeps 2
  • 5 nights min
  • Child friendly
  • Car not necessary
  • Private garden

Certificate of Excellence

from £65 / night

£455 / week

Book View

Responds fast!
avg. 3 hours 46 minutes

from £65 / night

(7) Excellent 

16

Windsor holiday apartment let

Windsor and Maidenhead / Windsor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden

from £150 / night

£799 - £1,200 / week

Book View

from £150 / 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 - £1,250 / week

Book View

from £75 / night

(3) 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

Book View

Responds fast!
avg. 3 hours 56 minutes

from £300 / night

(13) Excellent 

18

Holiday cottage in Holyport

Windsor and Maidenhead / Holyport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“Fantastic stay” We had a fantastic stay for 2 nights in Elaine's cottage. It's exactly as described and we had no hesitation in recommending the cottage to anyone else considering to stay there. We really liked the location and the village which had
…see more

from £105 / night

£735 / week

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from £105 / 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

Book View

Responds fast!
avg. 2 hours 58 minutes

from £250 / night

18

Holiday apartment in Maidenhead

Windsor and Maidenhead / Maidenhead

1 4 2 nights min

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

from £115 / night

£805 / week

Book View

from £115 / night

(5) Excellent 

33

Old Windsor holiday cottage rental

Windsor / Old Windsor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
“Homely Elegance” How lovely it was to arrive at such a charming and elegant cottage after a long flight. The owner gave us a warm welcome and nothing was too much trouble. The cottage is beautifully appointed and had everything we needed plus a few l
…see more

from £160 / night

£1,120 / week

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from £160 / night

(2) Excellent 

12

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 £120 / night

£750 / week

Book View

from £120 / night

(40) Excellent 

24

Ascot holiday apartment rental

Windsor and Maidenhead / Ascot

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 110 km
  • Child friendly
  • Car not necessary

from £131 / night

£890 / week

Enquire View

from £131 / 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. 59 minutes

from £110 / night

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

(12) Excellent 

24

Holiday cottage in Windsor

Windsor and Maidenhead / Windsor

2 4 4 nights min

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

from £145 / night

£1,120 - £1,195 / week

Book View

Responds fast!
avg. 1 hour 46 minutes

from £145 / night

(1) 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

(1) Very Good 

13

Holiday home in Windsor

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden

from £180 / night

£700 - £1,200 / week

Book View

from £180 / night

(2)  

7

Cottage rental in Maidenhead Riverside

Maidenhead / Maidenhead Riverside

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £75 / night

£525 - £1,250 / week

Book View

from £75 / night

17

Ascot holiday home rental

Windsor and Maidenhead / Ascot

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Child friendly
  • Private garden

from £295 / night

£2,065 / week

Book View

Responds fast!
avg. 2 hours 52 minutes

from £295 / night

(1) Excellent 

41

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 £162 / night

£1,000 - £2,133 / week

Book View

Responds fast!
avg. 1 hour 28 minutes

from £162 / night

26

Holiday townhouse in Windsor

Windsor and Maidenhead / Windsor

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary

from £110 / night

£770 / week

Book View

from £110 / 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 16 minutes

from £895 / 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 41 minutes

from £125 / night

Top Destination reviews

Windsor Forest Court
Cozy home away from home

We spent a wonderful 3 weeks in the two bedroom and 3 bedroom apartments. Bob and Lisa were very helpful, and accommodating. We requested daily cleaning and the cleaning staff were efficient and friendly. The location is ideal if you're traveling with younger children and want to be away from the hustle and bustle of city life. We were quite disappointed with the linens and bedding in general, which we found to be very old and mismatched. We will definitely stay here again!see more
Manor View
Lovely Apartment

Brilliant apartment in a great location for Legoland, London etc. Very clean with everything that we needed for a lovely stay. … see more
2 double bedroom modern house with secure parking
Fantastic

A fabulous accommodation which is spotlessly clean and very well equipped. The owners are extremely friendly, helpful and welcoming. The accommodation is in an excellent location for Legoland, Windsor, Runnymede and Savill Gardens. We would highly recommend this holiday home. … see more
Windsor Garden Lodge-Only 5 minutes from Legoland, Lapland UK & town centre.
Welcoming and homely

We had a lovely stay at WIndsor Garden Lodge. The owners were helpful and welcoming and the welcome basket on arrival was great after a long journey. The property was great for children and the large outdoor space for them to play and let off steam was ideal. The property was clean and well maintained. It is a great base for exploring Windsor and beyond. We would love to visit again in the future.see more
Eton/Windsor
A beautiful period cottage, well equipped and in a great location.

The cottage is tucked away in a very quiet location off the High Street in Eton but just a few minutes' walk from the Thames and Windsor with its attractions, excellent shops, restaurants and bars. It is beautifully furnished and extremely well equipped with everything you could possibly need for a very comfortable stay. Bridget prepared a 'welcome basket' which was very much appreciated. We stayed 3 nights and would have loved to stay longer. I would have no hesitation in recommending this property to others.see more
Rose Cottage - Listed 16th Century Cottage
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! … see more