Cottages in Berkshire and Self catering accommodation - Holiday Lettings - Holiday Rentals Berkshire

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179 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

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Responds fast!
avg. 2 hours 11 minutes

from £140 / night

6

Finchampstead holiday log cabin rental

Wokingham / Finchampstead

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly
  • Pet friendly

from £92 / night

£645 - £795 / week

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Responds fast!
avg. 3 hours 42 minutes

from £92 / night

10

Home rental in Finchampstead

Wokingham / Finchampstead

2 5 3 nights min

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

from £60 / night

£405 - £595 / week

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Responds fast!
avg. 3 hours 42 minutes

from £60 / night

(9) Excellent 

24

Holiday farmhouse in Padworth

Berkshire / Padworth

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
“A lovely house, with a great kitchen and gardens.” A warm welcome, great value and good facilities. All the mod cons you would expect from a hotel, but with all the added home comforts of a holiday home. We could only stay for one night but would ha
…see more

from £140 / night

£910 / week

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from £140 / night

22

Holiday guest house with golf nearby in Cookham Dean

Berkshire / Cookham Dean

1 4 2 nights min

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

from £85 / night

£555 / week

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from £85 / 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 35 minutes

from £195 / night

13

Home rental in Finchampstead with shared pool

Wokingham / Finchampstead

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly

from £60 / night

£405 - £595 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from £60 / 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
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from £135 / night

£945 / week

Book View

Responds fast!
avg. 1 hour 14 minutes

from £135 / night

(3) Very Good 

6

Holiday chalet in Finchampstead

Wokingham / Finchampstead

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly

from £60 / night

£405 - £595 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from £60 / night

(28) Excellent 

20

Holiday cottage in Waltham St Lawrence

Berkshire / Waltham St Lawrence

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 0 km
  • Child friendly

from £160 / night

£950 - £1,300 / week

Enquire View

from £160 / night

(24) Excellent 

Certificate of Excellence

18

Holiday cottage rental

Newbury / Enborne

2 4 2 nights min

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

Certificate of Excellence

from £65 / night

£440 / week

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from £65 / night

12

Holiday home in Finchampstead

Wokingham / Finchampstead

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £92 / night

£645 - £795 / week

Book View

Responds fast!
avg. 3 hours 0 minutes

from £92 / 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
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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
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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
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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
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Certificate of Excellence

from £150 / night

£1,050 / week

Book View

Responds fast!
avg. 3 hours 2 minutes

from £150 / night

(1) Excellent 

47

Holiday home rental

Berkshire / Cookham Dean

4 8 Min stay varies

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

from £250 / night

£1,750 / 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 - £1,250 / week

Book View

from £75 / night

(2) Average 

11

Holiday home in Finchampstead

Wokingham / Finchampstead

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly

from £92 / night

£645 - £795 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from £92 / night

8

Holiday log cabin in Finchampstead

Wokingham / Finchampstead

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly

from £78 / night

£545 - £725 / week

Book View

Responds fast!
avg. 3 hours 0 minutes

from £78 / 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
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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

8

Newbury holiday apartment rental

Berkshire / Newbury

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly

from £140 / night

£980 / week

Book View

Responds fast!
avg. 1 hour 54 minutes

from £140 / 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

(1) Very Good 

10

Holiday home in Finchampstead

Wokingham / Finchampstead

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Child friendly

from £92 / night

£645 - £795 / week

Book View

Responds fast!
avg. 3 hours 42 minutes

from £92 / 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
“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.
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from £160 / night

£1,120 / week

Book View

Responds fast!
avg. 2 hours 11 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 35 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
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from £105 / night

£735 / week

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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

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
PADLEY BARN, detached stone barn conversion, underfloor heating, woodburner
A comfortable and well equipped house in a stunning location.

The location is absolutely wonderful! In the heart of Swaledale with stunning views of the moors. A great walking area and close to several charming villages. The cottage is very well equipped, extremely comfortable, clean and attractive. You can walk into the beautiful countryside straight from the front door but if you want a pub or a shop you'll need to travel several miles - we loved the peace and quiet. The surrounding moors are home to many sheep, grouse and rabbits and the neighbouring chickens and cat may pay you a visit which our children enjoyed. The owner is very helpful and responsive and the house contains lots of local information and detailed maps which were very useful.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