45 Best Vacation Rentals in Windsor - Holiday Lettings - Cabins

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49 Vacation rentals

(2) Excellent 

4

Home rental in Eton

Windsor / Eton

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Car not necessary
  • 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 $635 / night

$4445 / week

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from $635 / night

(20) Excellent 

23

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 $159 / night

$1112 / week

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from $159 / night

(37) 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 $134 / night

$934 / week

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from $134 / night

(7) 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 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 $572 / night

$3556 - $3810 / week

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from $572 / night

(1) Excellent 

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 $242 / night

$2001 / week

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from $242 / night

(2) 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 $381 / night

$2540 / week

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from $381 / night

(16) Very Good 

Certificate of Excellence

13

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 $110 / night

$591 - $762 / week

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Responds fast!
avg. 2 hours 22 minutes

from $110 / night

(9) Very Good 

Certificate of Excellence

23

Eton Vacation apartment rental

Windsor / Eton

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night 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 $190 / night

$1325 / week

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Responds fast!
avg. 3 hours 38 minutes

from $190 / night

9

Apartment rental in Windsor

Windsor and Maidenhead / Windsor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 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 $172 / night

$699 / week

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Responds fast!
avg. 2 hours 36 minutes

from $172 / night

(1) Excellent 

9

Windsor 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 $89 / night

$623 / week

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from $89 / night

(9) Excellent 

Certificate of Excellence

18

Vacation 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
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 $223 / night

$1556 / week

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Responds fast!
avg. 3 hours 0 minutes

from $223 / night

(1) Very Good 

11

Home rental in Windsor

Windsor and Maidenhead / Windsor

5 6 1 night min

  • 5 bedrooms
  • Sleeps 6
  • 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 $331 / night

$2312 / week

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from $331 / night

(4) Very Good 

17

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 $108 / night

$756 - $991 / week

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from $108 / night

(7) Excellent 

16

Windsor Vacation apartment rental

Windsor and Maidenhead / Windsor

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • 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 $159 / night

$1015 - $1461 / week

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from $159 / night

51

Home rental in Windsor

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 $206 / night

$1439 - $2544 / week

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Responds fast!
avg. 52 minutes

from $206 / 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 $83 / night

$578 / week

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from $83 / night

(38) 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. 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

Certificate of Excellence

from $178 / night

$1245 / week

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Responds fast!
avg. 3 hours 48 minutes

from $178 / night

(1) Excellent 

14

Old Windsor Vacation studio rental

Windsor / Old Windsor

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • 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 $121 / night

$845 / week

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Responds fast!
avg. 1 hour 59 minutes

from $121 / night

(10) 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 $229 / night

$1601 / week

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Responds fast!
avg. 3 hours 48 minutes

from $229 / 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 $159 / night

$826 - $896 / week

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from $159 / night

13

Vacation apartment rental

Windsor and Maidenhead / Windsor

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • 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 $121 / night

$826 - $889 / week

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from $121 / night

(1) Excellent 

12

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Car not necessary
1 bedroom apartment located in central Windsor. Only a two minutes 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 a …see more

from $121 / night

$845 / week

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Responds fast!
avg. 2 hours 0 minutes

from $121 / night

(4) Excellent 

Certificate of Excellence

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 Br …see more

Certificate of Excellence

from $223 / night

$1556 / week

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Responds fast!
avg. 3 hours 0 minutes

from $223 / 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 $185 / night

$1423 - $1518 / week

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Responds fast!
avg. 1 hour 38 minutes

from $185 / night

(7) Excellent 

Certificate of Excellence

16

Windsor 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

Certificate of Excellence

from $108 / night

$756 - $839 / week

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Responds fast!
avg. 1 hour 46 minutes

from $108 / night

(1) Very Good 

13

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
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 $157 / night

$889 - $953 / week

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from $157 / night

15

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
This stunning apartment is set over two floors with the second floor accessed by a spiral staircase. This is a lovely period apartment set in a former convent with period features and lots of character yet is fully modernised with new bathrooms and a modern tiled kitch …see more

from $172 / night

$1080 - $1137 / week

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from $172 / night

7

Windsor Vacation home rental

Windsor and Maidenhead / Windsor

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Private garden
A charming period house next to The Long Walk in Windsor with views of Windsor Castle. Two bedrooms upstairs (one double and one with pull-out trundle bed) plus a further bonus room downstairs with sofa bed and desk. One new bathroom with shower over the bathtub plus a …see more

from $155 / night

$1080 - $1175 / week

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from $155 / 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 $105 / night

$731 / week

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from $105 / 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 $318 / night

$1905 / week

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from $318 / night

12

Vacation b&b rental

Windsor and Maidenhead / Windsor

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
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 $115 / night

$801 / week

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from $115 / night

(9) Excellent 

24

Windsor 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 $318 / night

$2032 / week

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Responds fast!
avg. 2 hours 3 minutes

from $318 / night

(2) 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 $178 / night

$1245 / week

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Responds fast!
avg. 3 hours 48 minutes

from $178 / night

(6) 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 $635 / night

$3112 - $5246 / week

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from $635 / night

18

Windsor Vacation apartment rental

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • 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 $120 / night

$820 - $1334 / week

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Responds fast!
avg. 1 hour 48 minutes

from $120 / night

(13) 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 $318 / night

$1905 / week

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from $318 / night

12

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Car not necessary
Newly refurbished in 2015 to include a new kitchen, bathroom, flooring, carpets and redecoration plus all new furniture. Two bedrooms, one bathroom and extra WC. Balcony. Off street parking and walking distance to town centre (within 6 minutes). This is a fabulous prope …see more

from $119 / night

$826 / week

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from $119 / 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 $121 / night

$826 - $985 / week

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from $121 / 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 $102 / night

$572 - $750 / week

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from $102 / 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 $153 / night

$1067 - $1334 / week

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from $153 / night