40 Best Vacation Rentals in Windsor - Holiday Lettings - Cabins

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41 Vacation rentals

(31) Excellent 

28

Vacation cottage in Berkshire

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
This beautiful unique 18th century cottage retains its original character combined with 21st century facilities and five star amenities. An open plan ground floor style makes it ideal for families and entertaining. The kitchen leads onto a secure rear garden with outs  …see more

from $124 / night

$867 - $1217 / week

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from $124 / night

(13) Excellent 

40

Vacation home in Berkshire

Windsor and Maidenhead / Windsor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
Recently (December 2015) acquired by us, and receiving all 5* reviews, this charming detached Grade ll listed 16th Century cottage offers an abundance of beautiful character features. Nestled behind secure gates, in mature gardens in this charming Buckinghamshire vill  …see more

from $149 / night

$1042 / week

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from $149 / night

(7) Very Good 

13

Vacation apartment accommodation

Windsor and Maidenhead / Windsor

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Car not necessary
My lovely apartment is advertised for short term lettings (maximum one month stay) and features: - Car parking space - Sofa bed for an additional 2 adults - Sky TV & Wifi - Less than 1 minute walk to the town centre - 5 minutes drive to Legoland The apartment has one  …see more

from $113 / night

$750 - $838 / week

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from $113 / night

(14) Very Good 

13

Vacation apartment in Berkshire

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
Manor View is a cosy and comfortable self-catering holiday apartment in Windsor, Berkshire, providing accommodation for up to 4 people (and a baby) in 2 bedrooms. The property is attractively situated on the top floor of a purpose built apartment block, tucked away in t  …see more

from $108 / night

$582 - $750 / week

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from $108 / night

(4) Excellent 

18

Vacation home in Berkshire

Windsor and Maidenhead / Windsor

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Eton/Windsor In the heart of Eton High Street, 2 minutes walk to Windsor Castle or Eton College. A unique opportunity to holiday in a 400 year old, grade 2 listed cottage, exposed beams. Boutique accommodation. Bespoke fitted kitchen, Neff appliances and double oven B  …see more

from $188 / night

$1313 / week

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from $188 / night

(4) Very Good 

22

Vacation apartment in Berkshire

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
9 The Courtyard is a well-appointed apartment situated in a secluded courtyard setting, with direct access to Windsor High Street. Just opposite is the Guildhall and a few steps away is the entrance to Windsor Castle, the largest castle in occupation. A short walk furth  …see more

from $107 / night

$744 - $975 / week

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from $107 / night

(3) Excellent 

16

Berkshire Vacation home rental

Windsor and Maidenhead / Windsor

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Town Centre Location with allocated parking. Beautiful secluded one-bedroom character cottage situated just a stone's throw from Windsor town centre shops & restaurants. Quiet mews area incorporating communal lawn area. The property has been totally modernised to inc  …see more

from $107 / night

$744 - $825 / week

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from $107 / night

(3) Very Good 

18

Eton Vacation home rental

Windsor / Eton

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
Eton/Windsor In the heart of Eton High Street, 2 minutes walk to Windsor Castle or Eton College. A unique opportunity to holiday in a 400 year old, grade 2 listed cottage, exposed beams. Boutique accommodation. Bespoke fitted kitchen, Neff appliances and double oven B  …see more

from $188 / night

$1313 / week

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from $188 / night

20

Old Windsor Vacation cottage rental

Windsor / Old Windsor

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The Cottage is set on a quiet country road, directly opposite the magnificent Windsor Great Park, with spectacular views of Windsor Castle. It's a super warm, super cosy cottage, with a lovely garden in a unique location, on a quiet and private estate of four houses.  …see more

from $238 / night

$1969 / week

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from $238 / night

(7) Very Good 

25

Eton Vacation apartment rental

Windsor / Eton

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
A charming and characterful period two bedroom apartment on Eton High Street. 3 minutes walk to Windsor & Eton train station and fantastic shops, cafes restaurants gallerys and antique shops all within very easy reach. This lovely apartment matches modern living with o  …see more

from $150 / night

$750 / week

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from $150 / night

(7) Excellent 

16

Berkshire Vacation apartment rental

Windsor and Maidenhead / Windsor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Superb, bright, modern, spacious 2 bedroom, 2 bathroom apartment with parking in gated development a short walk from Windsor town centre. Large entrance hall, modern luxury kitchen with built in dishwasher and washing machine, spacious lounge/diner with double doors  …see more

from $125 / night

$750 - $1250 / week

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from $125 / night

(1) Very Good 

11

Home rental in Berkshire

Windsor and Maidenhead / Windsor

5 5 1 night min

  • 5 bedrooms
  • Sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden
Extensive and spacious living accomodation set in beautiful sourroundings An amazing Range master cooker, granite work top , full working kitchen with table and chairs , and a breakfast bar with stools. crockery and utensils ,all mod cons . Wooden flooring throughout  …see more

from $325 / night

$2275 / week

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from $325 / night

(5) Excellent 

40

Vacation 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
Chateau Gato is a tranquil riverside haven nestled on a secluded leafy bend of the River Thames in Wraysbury. Minutes from the historic town of Windsor and the academic town of Eton. Chateau Gato provides the perfect retreat with a homely and charming atmosphere, a pea  …see more

from $625 / night

$3063 - $5163 / week

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from $625 / night

(4) Very Good 

26

Old Windsor Vacation cottage rental

Windsor / Old Windsor

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The old wharf cottage is a beautiful riverside retreat nestled between two islands on the picturesque banks of the River Thames. Situated minutes from the historic town of Windsor and Eton as well as 40 minutes from the attractions of central London. Watch the river go  …see more

from $500 / night

$3750 - $4000 / week

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from $500 / night

(4) Very Good 

12

Studio rental in Berkshire 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
Sleeping one or two with a single or twin beds, which may form a double; this studio apartment in Datchet, near Windsor, is available to rent weekly or longer for business or holiday lets. It is fully equipped for one or two people, with all towels, T-towels and bed li  …see more

from $82 / night

$569 / week

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from $82 / night

(12) Very Good 

45

Vacation apartment in Berkshire

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
The Clockhouse is full of charm and character. There is a large bedroom/living room which features a double bed and an extra bed can be arranged if required. The comfortable bedroom has ample wardrobe space. There is a shower room on the ground floor, featuring a shower  …see more

from $150 / night

$1050 - $1313 / week

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from $150 / night

(12) Excellent 

24

Vacation cottage in Berkshire

Windsor and Maidenhead / Windsor

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Private garden
Willow Cottage is a beautiful and unique self catered holiday cottage set in a rural village but only minutes away from Windsor in Berkshire and 15 minutes from Heathrow airport. The cottage is perfect for a couple wanting to spend a peaceful few days away or a family n  …see more

from $182 / night

$1400 - $1494 / week

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from $182 / night

11

Berkshire Vacation apartment rental

Windsor and Maidenhead / Windsor

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
This beautiful character Central Windsor apartment with high ceilings and wooden floors is in a great location close to everything! ...Windsor Castle, beautiful crisp river walks, Alexandra Gardens, Eton College, train stations, bus routes and tucked away just a few min  …see more

from $124 / night

$749 - $1012 / week

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from $124 / night

10

Vacation apartment in Berkshire

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Car not necessary
New 1 bedroom apartment located in central Windsor. Only two minutes walk away from Windsor Castle and The Long Walk and also Windsor's restaurants and shops! Perfect for a weekend away! The apartment is 35m2 and consists of one double bedroom, open plan kitchen / li  …see more

from $119 / night

$832 / week

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from $119 / night

(35) Excellent 

23

Vacation studio in Berkshire

Windsor and Maidenhead / Windsor

Studio 4 2 nights min

  • Studio
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
This simple and beautiful Garden Studio is located in the stunning countryside of Oakley Green, Windsor, Berkshire. The Garden Studio is located on our family small-holding called Willow Court Farm. The Garden Studio is an absolutely perfect (simple and cosy) base for a  …see more

from $150 / night

$1050 / week

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from $150 / night

9

Apartment rental in Berkshire

Windsor and Maidenhead / Windsor

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
Second floor apartment in central Windsor two minute walk from town centre , Castle, pubs and restaurants . Private parking space , fully furnished Fully equipped and very comfortable and quiet Underfloor heating bath and walk in shower double glazed very private H  …see more

from $124 / night

$867 / week

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from $124 / night

18

Berkshire Vacation apartment rental

Windsor and Maidenhead / Windsor

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Child friendly
  • Car not necessary
Spacious two bedroom apartment with two bathrooms in this popular gated development of apartments just a short walk from Windsor Castle and shops. The property has a fully fitted kitchen with dishwasher and washer dryer. Two double bedrooms and two bathrooms, one with s  …see more

from $118 / night

$807 / week

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from $118 / night

(4) Excellent 

15

Home rental in Berkshire

Windsor and Maidenhead / Windsor

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Nearest beach 101 mi
  • Suitable for children age 5+
  • Private garden
Groom's House is perfectly situated for trips into Windsor, Ascot, Bray and surrounding areas with central London conveniently under an hour away.Guests of the house are welcome to explore the expansive Windsor Great Park.There are 4 double/twin bedrooms (2 per room) an  …see more

from $1125 / night

$6250 - $7500 / week

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from $1125 / night

(8) Excellent 

21

Berkshire Vacation lodge rental

Windsor and Maidenhead / Windsor

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
This beautiful contemporary Garden Lodge has been recently refurbished throughout and is located in the stunning countryside of Oakley Green, Windsor, Berkshire. It is located on our family small-holding called Willow Court Farm & is an absolutely perfect (simple and co  …see more

from $175 / night

$1225 / week

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from $175 / night

4

Home rental in Eton

Windsor / Eton

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Private garden
Unique former Eton boathouse directly on the River Thames, totally remodelled with charm and style. Steps to Eton boarding school and Windsor castle. Easy access to London and LHR, Legoland and many other amazing attractions. Chill by the river or run around the town  …see more

from $625 / night

$4375 / week

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from $625 / night

51

Home rental in Berkshire

Windsor and Maidenhead / Windsor

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Riverside,"Pixie Place", detached house, luxuriously furnished,, 4 bedrooms, it is located in Royal Borough of Windsor, West London, U.K. Royal Windsor is the first choice town for international tourists visiting the United Kingdom. We are pleased to offer for holiday  …see more

from $203 / night

$1325 - $2504 / week

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from $203 / night

9

Berkshire Vacation apartment rental

Windsor and Maidenhead / Windsor

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Suitable for children age 5+
The Loft Windsor is located on the corner of Beaumont Road and St Leonards Road, a small, quaint and atmospheric road, 10 minutes walk from the centre of Windsor, the pedestrian shopping zone, Windsor Castle and train station, with travel to central London taking just  …see more

from $88 / night

$613 - $700 / week

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from $88 / night

(34) Excellent 

52

Vacation home rental

Windsor and Maidenhead / Windsor

4 7 Min stay varies

  • 4 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
'Pixie Place', Riverside, detached house, luxuriously furnished, 3.5 bedrooms, it is located in Royal Borough of Windsor, West London, U.K.Royal Windsor is the first choice town for international tourists visiting the United Kingdom. We are pleased  …see more

from $179 / night

$1250 - $2313 / week

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from $179 / night

(9) Excellent 

24

Berkshire Vacation home rental

Windsor and Maidenhead / Windsor

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Ask about pets
  • Private garden
Willow Court is a lovely, spacious, light filled home. Located in a semi rural setting just outside of Windsor (3 miles), in the heart of polo country (Royal Berks Polo Club and Guards Polo Club are both within easy reach). Yet also within easy reach of Central London.  …see more

from $313 / night

$2000 / week

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from $313 / night

12

Vacation b&b rental

Windsor and Maidenhead / Windsor

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
A warm welcome awaits you at this lovely house built in the late 1700's. A spacious lounge is at your disposal and Jan or Richard will offer you home-made cake and a cup of tea or coffee. In Winter the fire will be lit. Comfy beds and a bottle of beer or cider in  …see more

from $113 / night

$788 / week

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from $113 / night

(13) Excellent 

24

Vacation townhouse in Berkshire

Windsor and Maidenhead / Windsor

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
Luxurious, modern and comfortable townhouse with stunning views of the river Thames and Windsor Castle. The perfect location for exploring London and surrounding area. Only 5 minutes to Legoland and 30 minutes to London by train. Funished to the highest standards c  …see more

Pricing unknown

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Pricing unknown

22

Vacation apartment rental

Windsor and Maidenhead / Windsor

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
In Central Windsor, this apartment is in a great location close to everything! ...Windsor Castle, Eton, leisure centre, train stations, bus routes, Windsor Royal shopping centre, Alexandra Gardens, beautiful river walks, tennis club, convenience stores, all a short walk  …see more

from $119 / night

$619 / week

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from $119 / night

12

Vacation apartment rental

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
Spacious apartment on the second floor of this executive apartment block. Electric gates to private parking area. Two bedrooms and two bathrooms. Master bedroom is ensuite, second bedroom has twin beds. Large kitchen with all modern appliances including washer-dryer,  …see more

from $157 / night

$813 - $1063 / week

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from $157 / night

15

Vacation home in Berkshire

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Lovely two bedroom cottage in the centre of Windsor with private off-road parking. Two bedrooms (one double one twin), new bathroom with shower over bath tub, combined living/dining room with leather sofas and flat screen TV. Small enclosed outside patio space a  …see more

from $119 / night

$813 - $1032 / week

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from $119 / night

4

Vacation guest house in Berkshire

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Suitable for children age 5+
The Ascot Room has the additional benefit of being accessed with its own entrance door from the front of the house without any steps to negotiate. The Ascot Room offers a five foot King size bed and an ensuite bathroom with bath/shower. There is the option of adding an  …see more

from $113 / night

$788 / week

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from $113 / night

(1) Very Good 

13

Vacation home in Berkshire

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Charming two bedroom holiday cottage in Windsor with one double bedroom and second bed room with twin beds (pull out). Two sofas (one is a sofa bed) and dining table with four chairs.One bathroom with shower and tub very close to town centre yet tucked away in t  …see more

from $149 / night

$875 - $1063 / week

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from $149 / night

15

Vacation apartment in Berkshire

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
A quirky two bedroom two bathroom apartment in a former convent about one mile from Windsor town centre. This apartment is set in lovely grounds and has plenty of parking. It is located on the first floor and has a lovely spiral staircase to the top floor bedroom with v  …see more

from $150 / night

$844 - $1157 / week

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from $150 / night

14

Windsor / Old Windsor

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from $150 / night

$1050 / week

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from $150 / night

16

Windsor and Maidenhead / Windsor

7 14 2 nights min

  • 7 bedrooms
  • Sleeps 14
  • 2 nights min
  • Suitable for children age 5+
  • Private garden

 …see more

from $1125 / night

$6125 - $7500 / week

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from $1125 / night

5

Windsor and Maidenhead / Windsor

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Private garden

 …see more

from $161 / night

$1125 / week

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from $161 / night

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