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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1,014 Holiday homes

(42) 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

from £115 / night

£805 / week

Book View

Responds fast!
avg. 2 hours 9 minutes

from £115 / night

(2) Excellent 

12

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Car not necessary

from £88 / night

£616 / week

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from £88 / 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

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from £300 / night

(29) 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 also a conservatory if it's not quite warm enough for alfresco dining! Perfect location for Thorpe park (20 mins), Legoland (10 mins), Chessington world of adventures (50mins), as well as all London and Windsor sites. Supermarket 2 minutes away. Would recommend to all. Very easy booking process and the in depth information we revived via an E book was invaluable. Thank you for a wonderful stay - we will definitely return, if not this year then definitely next year!

from £135 / night

£945 / week

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Responds fast!
avg. 2 hours 9 minutes

from £135 / night

31

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

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

Responds fast!
avg. 3 hours 33 minutes

from £180 / 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 £110 / night

£700 - £770 / week

Book View

Responds fast!
avg. 3 hours 58 minutes

from £110 / 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

from £500 / night

£2,800 - £3,500 / week

Book View

from £500 / 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

34

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 £128 / night

£896 / week

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from £128 / 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

(15) Excellent 

21

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
“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 hamper and prosecco and we hope to return again very soon.

from £175 / night

£1,225 / week

Book View

Responds fast!
avg. 2 hours 11 minutes

from £175 / 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

Responds fast!
avg. 3 hours 33 minutes

from £210 / 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 £630 / night

£3,400 - £5,640 / week

Book View

Responds fast!
avg. 3 hours 9 minutes

from £630 / 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

Responds fast!
avg. 3 hours 33 minutes

from £195 / night

(24) 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 - £615 / week

Book View

Responds fast!
avg. 1 hour 39 minutes

from £105 / night

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

Responds fast!
avg. 3 hours 33 minutes

from £195 / 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

from £250 / 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

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

(1) 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

Book View

from £129 / night

6

Holiday private room in Windsor

Windsor and Maidenhead / Windsor

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Car not necessary

from £120 / night

£780 / week

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from £120 / night

12

Holiday apartment rental

Windsor and Maidenhead / Windsor

2 4 7 nights min

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

from £100 / night

£650 - £770 / week

Book View

Responds fast!
avg. 3 hours 58 minutes

from £100 / 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 - £650 / week

Book View

from £75 / night

(9) Excellent 

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 11 minutes

from £175 / 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) 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

£1,100 - £2,133 / week

Book View

Responds fast!
avg. 1 hour 27 minutes

from £162 / night

(3) Excellent 

4

Home rental in Eton

Windsor / Eton

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Private garden

from £550 / night

£3,850 / week

Book View

from £550 / night

(2) Very Good 

19

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary

from £120 / night

£915 - £935 / week

Book View

Responds fast!
avg. 3 hours 58 minutes

from £120 / 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 51 minutes

from £145 / 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 8 minutes

from £155 / 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

from £160 / night

£1,120 / week

Book View

from £160 / 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. 55 minutes

from £110 / night

(14) 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

from £105 / night

£735 / week

Book View

from £105 / night

(6) 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 46 minutes

from £85 / 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

Responds fast!
avg. 3 hours 33 minutes

from £195 / 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 - £950 / week

Book View

from £120 / night

(39) 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 36 minutes

from £185 / 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

Book View

Responds fast!
avg. 2 hours 52 minutes

from £125 / night

(2) Excellent 

14

Holiday apartment letting

Windsor and Maidenhead / Windsor

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden

from £175 / night

£1,225 / week

Book View

Responds fast!
avg. 1 hour 36 minutes

from £175 / night

Top Destination reviews

Eton/Windsor
Lovely cottage, perfect location

We had a lovely 3 night stay in this delightful cottage. The cottage had everything we needed and the gorgeous welcome basket was much appreciated. It's ideally located for Windsor castle and restaurants and pubs. We did not use our car at all during the stay. We also had a day trip in to London just 45 mins on the train from Windsor station. We would highly recommendsee more
Gorgeous Country Cottage beside Windsor Great Park & overlooking Windsor Castle
Cottage in Windsor

We thoroughly enjoyed our stay. Our hosts were so welcoming and the cottage is very sweet. It’s position is perfect, so close to the Great Park, Windsor itself and yet tucked away in a beautiful corner. Would definitely stay again. … see more
Rose Cottage - Listed 16th Century Cottage
Wonderful cottage ideally located

We absolutely loved our stay in this beautiful cottage perfect for cosy nights in as a family with everything you need. The owner was very helpful and always on hand to help if needed would love to come and stay again. Windsor is a beautiful place to visit and you are ideally located for travel further afar we enjoyed a day in London and to Hampton court palace as well as exploring Windsor and eton. We highly recommend this cottage to anyonesee more
Pretty contemporary open plan cottage with open fire.
Very cosy and nice cottage

Very nice and cute house, beautiful from inside and outside. The front garden is worth making a picture. Inside the rooms are clean and beautiful with very comfortable beds and wonderfully soft and airy duvets. The cottage is located in a beautiful area with very English countryside at its best, church is next to, birds are chirping around and green farms along the way.see more
Beautiful spacious detached family home 10 mins to Legoland
Willow Court

Very clean and comfortable. Perfect accommodation for 4 adults and 3 children, plenty of space and the ensuite bedrooms was a bonus. It rained whilst we were there so couldn’t use the outside space, but this would add to a stay as there is plenty of outdoor room to relax and play safely. Would highly recommend this home for short or longer stays.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