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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952 Holiday homes

36

Studio rental in Old Windsor

Windsor / Old Windsor

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies

from £140 / night

£980 / week

Book View

Responds fast!
avg. 2 hours 18 minutes

from £140 / night

(14) 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
“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 p
…see more

Certificate of Excellence

from £195 / night

£1,365 / week

Book View

Responds fast!
avg. 1 hour 42 minutes

from £195 / night

(27) 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
“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
…see more

from £135 / night

£945 / week

Book View

Responds fast!
avg. 1 hour 14 minutes

from £135 / night

(39) 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 14 minutes

from £115 / night

(39) Excellent 

Certificate of Excellence

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 ha
…see more

Certificate of Excellence

from £145 / night

£1,015 / week

Book View

Responds fast!
avg. 1 hour 42 minutes

from £145 / 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
“Wonderful family apartment” Quirky little apartment with all the creature comforts for family living. In walking distance to Windsor castle and Windsor itself with great shops and pubs. 10 minutes drive to legoland and within half hour to chessington
…see more

Certificate of Excellence

from £149 / night

£1,043 / week

Book View

Responds fast!
avg. 3 hours 26 minutes

from £149 / night

(13) 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
“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
…see more

Certificate of Excellence

from £150 / night

£1,050 / week

Book View

Responds fast!
avg. 3 hours 2 minutes

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

(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

from £88 / night

£616 / week

Book View

Responds fast!
avg. 2 hours 44 minutes

from £88 / night

(9) Excellent 

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
“Excellent house absolutely ideal for a visit to Legoland.” The house was excellent... great facilities...comfortable.... well equipped ...ideal for us with our three small grandchildren. It actually exceeded our expectations and we would certainly rec
…see more

from £195 / night

£1,875 - £2,100 / week

Book View

Responds fast!
avg. 1 hour 46 minutes

from £195 / 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

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 £100 / night

£700 - £850 / week

Book View

from £100 / night

10

Windsor holiday apartment rental

Windsor and Maidenhead / Windsor

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min

from £79 / night

£550 - £850 / week

Book View

from £79 / 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

£700 - £750 / week

Book View

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 £125 / night

£650 - £1,200 / week

Book View

from £125 / 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 38 minutes

from £250 / night

15

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

£625 - £1,200 / week

Book View

from £110 / night

(5) 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 - £780 / week

Book View

from £85 / 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. 2 hours 38 minutes

from £300 / 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 44 minutes

from £110 / 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

from £65 / night

(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

Book View

from £115 / night

(4) 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
“Stunning” We have had such a relaxing stay. Kids have loved it especially playing with Humphrey the dog. Totally recommend this cottage well located for visiting Legoland and Windsor Castle
…see more

from £160 / night

£1,120 / week

Book View

Responds fast!
avg. 2 hours 18 minutes

from £160 / night

(9) Excellent 

21

Holiday studio in Windsor

Windsor and Maidenhead / Windsor

Studio 4 2 nights min

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

from £145 / night

£1,015 / week

Book View

Responds fast!
avg. 1 hour 42 minutes

from £145 / 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
“Very comfortable home from home” Stayed here when we were walking the Thames Path from Reading to Maidenhead over 4 days. Very well equipped and a perfect place to return to in the evenings. Food at the local pub very good. Owner very helpful and welc
…see more

from £105 / night

£735 / week

Book View

from £105 / 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

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

Responds fast!
avg. 3 hours 29 minutes

from £89 / 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
“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, restaur
…see more

Certificate of Excellence

from £175 / night

£1,225 / week

Book View

Responds fast!
avg. 3 hours 2 minutes

from £175 / 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 45 minutes

from £295 / night

(6) 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 45 minutes

from £125 / 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

Book View

from £120 / night

(1) 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 £68 / night

£476 / week

Book View

from £68 / night

(14) Excellent 

24

Holiday townhouse in Windsor

Windsor and Maidenhead / Windsor

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Car not necessary
“Fantastic house, awesome location” A wonderful stay in a wonderful house, in a fantastic location, hidden away in the heart of Windsor & Eton. Beautifully appointed yet very useable, we stayed with extended family, used each and every floor but never
…see more

from £250 / night

£1,500 / week

Book View

Responds fast!
avg. 2 hours 38 minutes

from £250 / night

(4) Very Good 

11

Home rental in Windsor

Windsor and Maidenhead / Windsor

5 8 1 night min

  • 5 bedrooms
  • Sleeps 8
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £300 / night

£2,100 / week

Book View

from £300 / 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
“Brilliant House” The house was exactly what we required for our stay in the area. Comfortable beds and a fully equipped kitchen! lots of bits and bobs around which made it even more exciting! Only downfall would be that the fridge wasn't that cold!
…see more

from £500 / night

£2,800 - £3,500 / week

Book View

from £500 / night

14

Windsor holiday home rental

Windsor and Maidenhead / Windsor

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Private garden

from £111 / night

£775 - £1,400 / week

Book View

from £111 / night

21

Holiday home in Sunninghill

Ascot / Sunninghill

4 9 2 nights min

  • 4 bedrooms
  • Sleeps 9
  • 2 nights min
  • Child friendly
  • Pet friendly

from £1,500 / night

£7,000 / week

Book View

Responds fast!
avg. 2 hours 18 minutes

from £1,500 / 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

(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

£625 - £1,200 / week

Book View

from £180 / 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 36 minutes

from £145 / night

Top Destination reviews

Gorgeous Country Cottage beside Windsor Great Park & overlooking Windsor Castle
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 lovely surprises. We felt very much at home and wish to return. … see more
Windsor Garden Lodge-Only 5 minutes from Legoland, Lapland UK & town centre.
Fantastic Accommodation

I would highly recommend this accomodation, great for couples or small families. You are made to feel very welcome by your hosts, who also throw in a generous welcome pack which the kids loved. Will return! … see more
Pretty contemporary open plan cottage with open fire.
Excellent cottage in lovely location

We (2 adults, 2 young kids) stayed here as a base for Legoland, Chessington and we also visited Central London twice (took train from Cookham taking around 1 hour). It is a well finished, very clean, cosy cottage with everything we needed for our stay. The area is very picturesque with a community feel. It's quiet, and has a lovely local pub at bottom of the lane serving good food. The owner had left some goodies on arrival, and she was quick to reply to any queries. We really enjoyed our stay here and would highly recommend for visits around this area.see more
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
Rose Cottage - Listed 16th Century Cottage
Absolutely wonderful - full of charm and character

A really lovely cottage - bursting with 16th Century character and charm. Tastefully modernised and beautifully decorated - clearly by someone who knows what they are doing! Lots of interesting nooks and crannies and a lovely conservatory. Very helpful owner and, as and added bonus, there is a very quiet and cosy pub across the road. Will definitely come back.see more
Little Chauntry - 18th Century Cottage
Quality accommodation with high specification fitments

Only a mile or so from Junction 7 of the M4, this cottage has a rural feel tucked away with a small number of other properties. The accommodation has been delightfully decorated throughout with carefully placed design touches. The kitchen and lounge areas in particular have a spacious, light and airy feel.see more