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

Close

View larger map

Also consider

Europe Holidays
479632 properties
United Kingdom Holidays
59460 properties
Cottages Cornwall
2983 properties
Apartments Greater London
941 properties
Cottages Cumbria
2225 properties
Cottages Lake District
1840 properties
Cottages Devon
2810 properties
Cottages Central England / Cotswolds
940 properties
Cottages Dorset
819 properties
Cottages Isle of Wight
507 properties
Cottages Peak District / Derbyshire
460 properties
Cottages Somerset
610 properties
Cottages Kent
557 properties
Cottages Sussex
770 properties
Cottages Norfolk
1023 properties
Cottages Isle of Man
11 properties
Northumberland
640 properties
Cottages Yorkshire / Yorkshire Dales
1496 properties
Cottages England
41760 properties
Cottages Scotland
7758 properties
Apartments Edinburgh
1385 properties
Cottages Wales
7155 properties
Coastal Cottages
222 properties
Apartments Windsor
57 properties
Houses Maidenhead
18 properties

Windsor and Maidenhead

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

999 Holiday homes

(43) 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

from £115 / night

£805 / week

Book View

Responds fast!
avg. 1 hour 12 minutes

from £115 / night

(30) 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

from £135 / night

£945 / week

Book View

Responds fast!
avg. 1 hour 12 minutes

from £135 / night

(28) Very Good 

Certificate of Excellence

17

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • 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) 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

from £300 / 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 £375 / night

£2,082 / week

Book View

from £375 / 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

(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 - £3,500 / week

Book View

from £500 / night

(8) 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. 3 hours 39 minutes

from £125 / night

(18) 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

from £175 / night

£1,225 / week

Book View

Responds fast!
avg. 2 hours 31 minutes

from £175 / 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

Book View

from £53 / 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

(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 - £999 / week

Book View

from £150 / 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

(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 31 minutes

from £175 / 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

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

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 6 minutes

from £295 / 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 £110 / night

£770 - £950 / week

Book View

Responds fast!
avg. 2 hours 45 minutes

from £110 / 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 £240 / night

£1,680 / week

Book View

Responds fast!
avg. 2 hours 10 minutes

from £240 / 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

(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 5 minutes

from £110 / night

25

Studio rental in Old Windsor

Windsor / Old Windsor

Studio 4 2 nights min

  • Studio
  • sleeps 4
  • 2 nights min
  • Private garden

from £150 / night

£1,050 / week

Book View

from £150 / 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

(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 16 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 £190 / night

£1,330 / week

Book View

from £190 / night

(1) Excellent 

42

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

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 

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

23

Windsor holiday apartment rental

Windsor and Maidenhead / Windsor

2 4 7 nights min

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

from £89 / night

£595 / week

Book View

from £89 / 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 36 minutes

from £185 / 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 1 minutes

from £630 / night

(12) Very Good 

45

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets

from £120 / night

£840 - £1,050 / week

Book View

from £120 / 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 - £935 / week

Book View

Responds fast!
avg. 2 hours 45 minutes

from £131 / 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

(19) Excellent 

16

Holiday b&b in Old Windsor

Windsor / Old Windsor

3 2 1 night min

  • 3 bedrooms
  • sleeps 2
  • 1 night min
  • Nearest beach 80 km
  • Private garden

from £99 / night

£693 / week

Book View

Responds fast!
avg. 3 hours 18 minutes

from £99 / night

(16) Excellent 

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

from £230 / night

£1,610 / week

Book View

Responds fast!
avg. 1 hour 36 minutes

from £230 / 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 £60 / night

£420 - £600 / week

Book View

from £60 / night

(1) Excellent 

10

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 £60 / night

£560 / week

Book View

from £60 / 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

(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

Top Destination reviews

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
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