50 Best Vacation Rentals in Windsor - Holiday Lettings - Cabins

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3,857 Vacation rentals

(27) Excellent 

22

Vacation home in Windsor

Windsor and Maidenhead / Windsor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
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 village. It retains its original character combined with 21st century facili …see more

from $189 / night

$1,323 / week

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avg. 1 hour 14 minutes

from $189 / night

36

Studio rental in Old Windsor

Windsor / Old Windsor

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
The Little Hideaway is a romantic and rather magical studio, which makes the perfect getaway. This charming and newly finished two storey property is on a private estate once owned by King Henry 8th. This old estate sits on nine acres and lies directly opposite the ma …see more

from $196 / night

$1,372 / week

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avg. 2 hours 24 minutes

from $196 / night

(39) Excellent 

28

Vacation cottage in Windsor

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 $161 / night

$1,127 / week

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avg. 1 hour 14 minutes

from $161 / night

(13) Excellent 

Certificate of Excellence

21

Vacation 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
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 Bri …see more

Certificate of Excellence

from $210 / night

$1,470 / week

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Responds fast!
avg. 3 hours 2 minutes

from $210 / night

(8) Excellent 

Certificate of Excellence

26

Eton Vacation home rental

Windsor / Eton

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Eton/Windsor Superb location. Forget the car. Bus or taxi from outside Windsor Castle to Legoland (2 miles). Trains to London Waterloo and London Paddington both within 4/5 minutes walk. In the heart of Eton High Street, 2 minutes walk to Windsor Castle or Eton College …see more

Certificate of Excellence

from $245 / night

$1,715 / week

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avg. 3 hours 2 minutes

from $245 / 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
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

Certificate of Excellence

from $91 / night

$637 / week

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from $91 / 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
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 $420 / night

$2,940 / week

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from $420 / night

(4) Excellent 

33

Old Windsor Vacation cottage rental

Windsor / Old Windsor

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Pet friendly
The Victorian Lodge (1876) is a charming and quintessentially English country cottage on a private estate once owned by King Henry 8th. It sits at the entrance of a long driveway leading to the Little Dower House, the enchanting home where the owners of the Lodge live. …see more

from $224 / night

$1,568 / week

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avg. 2 hours 24 minutes

from $224 / night

(7) Excellent 

16

Windsor 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 $210 / night

$1,119 - $1,680 / week

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from $210 / night

(12) Excellent 

24

Vacation cottage in Windsor

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 $203 / night

$1,568 - $1,673 / week

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avg. 1 hour 36 minutes

from $203 / night

(14) Very Good 

Certificate of Excellence

23

Eton Vacation apartment rental

Windsor / Eton

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
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

Certificate of Excellence

from $209 / night

$1,461 / week

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Responds fast!
avg. 3 hours 26 minutes

from $209 / night

(9) Excellent 

21

Vacation studio in Windsor

Windsor and Maidenhead / Windsor

Studio 4 2 nights min

  • Studio
  • Sleeps 4
  • 2 nights min
  • Child friendly
This fantastic recently refurbished contemporary garden studio is modest in size but is very well designed & equipped to provide great accommodation for up to 2 adults and 2 children. The open plan studios provide a king size bed and full size bunk beds with an ensuit …see more

from $203 / night

$1,421 / week

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Responds fast!
avg. 1 hour 36 minutes

from $203 / night

(2) Excellent 

12

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Car not necessary
1 bedroom apartment located in central Windsor. Only a two-minute walk from Windsor Castle, The Long Walk and Windsor's restaurants and shops or just a 10-minute travel to Legoland! The apartment is 35m2 and consists of one double bedroom, open plan kitchen/living are …see more

from $124 / night

$863 / week

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avg. 2 hours 44 minutes

from $124 / night

(3) Excellent 

5

Vacation home in Eton

Windsor / Eton

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Child friendly
A superb, modern townhouse in an excellent location, within walking distance of Windsor Castle, the River Thames and Eton College. Walking distance to a mainline station with direct access to Central London and within 15 minutes drive of LEGOLAND, Thorpe Park and Royal …see more

from $420 / night

$2,800 / week

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avg. 2 hours 38 minutes

from $420 / night

(15) Excellent 

Certificate of Excellence

26

Windsor Vacation lodge rental

Windsor and Maidenhead / Windsor

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Private garden
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

Certificate of Excellence

from $273 / night

$1,911 / week

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Responds fast!
avg. 1 hour 36 minutes

from $273 / night

(10) Very Good 

25

Old Windsor Vacation cottage rental

Windsor / Old Windsor

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
The old wharf cottage is a beautiful thatched 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 …see more

from $700 / night

$3,920 - $4,900 / week

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from $700 / night

(2) Excellent 

12

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
A stylish two bedroom apartment superbly located just off Windsor's main High Street in an attractive Courtyard building with private off-road parking for one car. This super newly refurbished modern apartment has a new kitchen with granite worktops, a breakfast bar. Wo …see more

from $168 / night

$980 - $1,050 / week

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from $168 / night

(14) Excellent 

24

Vacation townhouse in Windsor

Windsor and Maidenhead / Windsor

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • 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

from $350 / night

$2,100 / week

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Responds fast!
avg. 2 hours 38 minutes

from $350 / night

5

Vacation home in Eton

Windsor / Eton

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
A 2 bedroom townhouse superbly located in Eton, next to the pedestrian bridge by the side of the River Thames that links Eton and Windsor. A kitchen/dining room on the ground floor with cloakroom, 2 ensuite bedrooms on the first floor, a living room with separate media …see more

from $350 / night

$2,100 / week

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avg. 2 hours 38 minutes

from $350 / night

(21) Very Good 

Certificate of Excellence

17

Vacation apartment in Windsor

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

Certificate of Excellence

from $146 / night

$658 - $861 / week

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Responds fast!
avg. 2 hours 10 minutes

from $146 / night

13

Vacation apartment rental

Windsor and Maidenhead / Windsor

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Child friendly
  • Car not necessary
Wonderful two bedroom apartment within 3-4 minutes' walk of Windsor town centre and a short stroll of lovely restaurants, shops and delicatessens. This property has been completely remodelled to include a new kitchen with granite worktops and a charming new bathroom wi …see more

from $154 / night

$840 - $980 / week

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from $154 / night

(1) Excellent 

41

Home rental in Windsor with golf nearby

Windsor and Maidenhead / Windsor

4 7 7 nights min

  • 4 bedrooms
  • Sleeps 7
  • 7 nights min
  • 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 $227 / night

$1,470 - $2,938 / week

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avg. 1 hour 12 minutes

from $227 / night

27

Vacation home in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Suitable for children age 5+
The property is just a short walk to the town’s excellent collection of clothes boutique, pubs, restaurants and tearooms, along with a wealth of attractions including boat trips on the River Thames, horse-drawn carriage rides through Windsor’s Great Park and Lego Land, …see more

from $131 / night

$912 - $1,209 / week

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from $131 / night

10

Windsor Vacation apartment rental

Windsor and Maidenhead / Windsor

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
This very comfortable one bedroom apartment is perfect for corporate lets or singles/couples relocating to Windsor. The apartment is located on the outskirts of Windsor but just a short drive (about 2 mins) to the centre of Windsor or approximately a 20 minute walk. …see more

from $110 / night

$770 - $1,190 / week

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from $110 / 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 $175 / night

$910 - $1,680 / week

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from $175 / night

13

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Private garden
An executive apartment in this impressive building on Hermitage Lane backing onto Windsor Great Park. This two bedroom, two bathroom apartment has a large open plan living / dining / kitchen with all appliances including double oven, dishwasher, washer-dryer and gas hob …see more

from $140 / night

$980 - $1,190 / week

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from $140 / night

15

Vacation 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
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 $154 / night

$875 - $1,680 / week

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from $154 / night

14

Vacation home in Windsor

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Private garden
A Victorian ‘home from home’ bed and breakfast which provides delightful accommodation in a quiet residential location, close to the River Thames and only a 10 minute riverside walk to Windsor Castle, Town Centre and stations with regular trains to London. The attractiv …see more

from $119 / night

$833 / week

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from $119 / night

(19) Excellent 

16

Vacation b&b in Old Windsor

Windsor / Old Windsor

3 2 1 night min

  • 3 bedrooms
  • Sleeps 2
  • 1 night min
  • Nearest beach 80 mi
  • Private garden
One of our bestsellers in Windsor – and a guest favourite! McMillans B&B Windsor is a large, comfortable property located in Old Windsor. Free WiFi access is available and free parking is possible on site. Each beautifully decorated room here will provide you with a TV …see more

from $138 / night

$961 / week

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from $138 / night

(5) Very Good 

18

Vacation apartment in Windsor

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 $119 / night

$833 - $1,092 / week

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from $119 / night

(39) Excellent 

Certificate of Excellence

22

Vacation studio in Windsor

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. Studio East is located on our family small-holding called Willow Court Farm. Studio East is an absolutely perfect (simple and cosy) base for a couple or a …see more

Certificate of Excellence

from $203 / night

$1,421 / week

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Responds fast!
avg. 1 hour 36 minutes

from $203 / night

(3) Very Good 

14

Old Windsor Vacation studio rental

Windsor / Old Windsor

Studio 3 1 night min

  • Studio
  • Sleeps 3
  • 1 night min
  • Child friendly
  • Car not necessary
My studio apartment is in a beautiful Victorian building with lots of character. 10 minute walk to Windsor town and the Castle makes this a lovely central spot to discover Windsor and the surrounding areas. You’ll love my place because of the high ceilings, the location …see more

from $154 / night

$1,078 / week

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Responds fast!
avg. 59 minutes

from $154 / night

(9) Excellent 

14

Windsor Vacation 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
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 $273 / night

$2,625 - $2,940 / week

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Responds fast!
avg. 1 hour 46 minutes

from $273 / night

(1) Excellent 

12

Vacation b&b rental

Windsor and Maidenhead / Windsor

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
The price quoted relates to two people in a double room. Ask us about other sized groups. 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 te …see more

from $140 / night

$980 / week

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Responds fast!
avg. 3 hours 15 minutes

from $140 / night

6

Vacation private room in Windsor

Windsor and Maidenhead / Windsor

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
This traditional Victorian House built back in 1890's, has been newly revamped and brought up to the newest and most tasteful standards, including a landscaped garden of more than 1,000 sqf. The house is located in the proximity of Windsor Central Station (five minutes …see more

from $112 / night

$630 - $826 / week

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from $112 / night

23

Windsor Vacation apartment rental

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 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 $125 / night

$833 / week

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Responds fast!
avg. 3 hours 29 minutes

from $125 / night

(12) Very Good 

45

Vacation apartment in Windsor

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 $168 / night

$1,176 - $1,470 / week

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from $168 / night

(1) Very Good 

13

Vacation 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
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 this me …see more

from $252 / night

$875 - $1,680 / week

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from $252 / night

(7) Very Good 

37

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 $882 / night

$4,760 - $7,896 / week

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Responds fast!
avg. 3 hours 7 minutes

from $882 / night

4

Vacation apartment rental

Windsor and Maidenhead / Windsor

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
A wonderful penthouse apartment in the very heart of the town centre and moments from Windsor Castle and the stunning Long Walk. Ideally placed to take advantage of the excellent range of shops, bars and restaurants that Windsor has to offer. Two train stations provide …see more

from $273 / night

$1,911 / week

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from $273 / night