50 Best Vacation Rentals in Windsor - Holiday Lettings - Cabins

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4,019 Vacation rentals

(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 $398 / night

$2,651 / week

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from $398 / night

(42) 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 $153 / night

$1,067 / week

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avg. 2 hours 9 minutes

from $153 / 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 $663 / night

$3,711 - $4,639 / week

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from $663 / 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 $146 / night

$928 - $1,021 / week

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avg. 3 hours 58 minutes

from $146 / night

13

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
A delightful and luxurious interior designed apartment situated in a new high class development in central Windsor. Ideally placed to take advantage of the excellent range of shops, bars and restaurants that Windsor has to offer. Two train stations provide links to Lon …see more

from $238 / night

$1,664 / week

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Responds fast!
avg. 3 hours 15 minutes

from $238 / night

(2) 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-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 $117 / night

$817 / week

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from $117 / 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 $132 / night

$858 - $1,017 / week

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avg. 3 hours 58 minutes

from $132 / 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 $332 / night

$1,988 / week

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from $332 / 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 $259 / night

$1,809 / week

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Responds fast!
avg. 3 hours 15 minutes

from $259 / night

(24) 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 $140 / night

$637 - $815 / week

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avg. 1 hour 59 minutes

from $140 / night

19

Apartment rental in Windsor

Windsor and Maidenhead / Windsor

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
A character two bedroom apartment with direct views of Windsor Castle in the heart of the town center. Just a 1 minute walk from the castle and 3 minutes from Eton. Ideally placed to take advantage of the excellent range of shops, bars and restaurants that Windsor has …see more

from $278 / night

$1,941 / week

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avg. 3 hours 15 minutes

from $278 / night

(15) Excellent 

21

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

from $232 / night

$1,624 / week

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avg. 2 hours 11 minutes

from $232 / 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 $146 / night

$1,021 / week

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avg. 55 minutes

from $146 / night

(29) 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 $179 / night

$1,248 / week

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avg. 2 hours 9 minutes

from $179 / night

(9) Excellent 

26

Eton Vacation home rental

Windsor / Eton

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • 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

from $232 / night

$1,624 / week

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avg. 2 hours 11 minutes

from $232 / night

31

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 $212 / night

$1,485 / week

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from $212 / 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 $146 / night

$928 - $994 / week

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avg. 3 hours 58 minutes

from $146 / night

(3) Excellent 

4

Home rental in Eton

Windsor / Eton

4 6 3 nights min

  • 4 bedrooms
  • Sleeps 6
  • 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 College boarding school and Windsor castle. Easy access to London and LHR, Legoland and many other amazing attractions. Chill by the river or run around …see more

from $729 / night

$5,103 / week

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from $729 / night

(1) Excellent 

12

Vacation apartment rental

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
A fabulous contemporary apartment tastefully decorated and ideally situated in the town centre. Superbly located, just two minutes walk to Windsor Castle and right in the centre of town for convenience to shops, cafes, restaurants, Theatre Royal and moments from Eton Co …see more

from $171 / night

$1,192 / week

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from $171 / 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 $133 / night

$928 / week

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Responds fast!
avg. 3 hours 15 minutes

from $133 / night

(15) 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 $197 / night

$1,377 / week

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Responds fast!
avg. 3 hours 31 minutes

from $197 / night

(6) Very Good 

12

Studio rental in Windsor with golf nearby

Windsor and Maidenhead / Windsor

Studio 2 4 nights min

  • Studio
  • Sleeps 2
  • 4 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 $87 / night

$696 / week

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avg. 3 hours 46 minutes

from $87 / night

16

Windsor Vacation apartment rental

Windsor and Maidenhead / Windsor

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
A delightful and luxurious interior designed central Windsor apartment. Ideally placed to take advantage of the excellent range of shops, bars and restaurants that Windsor has to offer. Only a 10 minute walk from Windsor Castle. Two train stations provide links to Lond …see more

from $258 / night

$1,802 / week

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avg. 3 hours 15 minutes

from $258 / 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 $199 / night

$1,059 - $1,324 / week

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from $199 / night

34

Vacation townhouse in Windsor

Windsor and Maidenhead / Windsor

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
BRAND NEW! Bright & spacious Central Windsor Apartment in a superb location, on bustling street in centre of Windsor with pubs, restaurants, & shops mere steps away! Ideally located in the heart of historic Windsor Town Centre, surrounded by grade II listed buildings, …see more

from $170 / night

$1,188 / week

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from $170 / night

(2) Very Good 

19

Vacation apartment in Windsor

Windsor and Maidenhead / Windsor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Car not necessary
Superb and spacious three bedroom apartment on the first floor of this desirable and hugely popular gated development just a short walk from Windsor town centre. Two double bedrooms and one twin room (with two single beds). Fully furnished to a high standard and inclu …see more

from $159 / night

$1,213 - $1,240 / week

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Responds fast!
avg. 3 hours 58 minutes

from $159 / night

(2) Excellent 

14

Vacation apartment rental

Windsor and Maidenhead / Windsor

1 4 2 nights min

  • 1 bedroom
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
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.(but not suitable for more than 2 adults I'm afraid). Studio South is one of our new de …see more

from $232 / night

$1,624 / week

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Responds fast!
avg. 1 hour 36 minutes

from $232 / night

(1) Very Good 

9

Apartment rental in Windsor

Windsor and Maidenhead / Windsor

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Car not necessary
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 $206 / night

$928 / week

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Responds fast!
avg. 2 hours 8 minutes

from $206 / night

(6) 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 $113 / night

$786 - $1,083 / week

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avg. 3 hours 46 minutes

from $113 / night

(1) Excellent 

41

Home rental in Windsor with golf nearby

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 $215 / night

$1,458 - $2,827 / week

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avg. 1 hour 27 minutes

from $215 / night

(16) Excellent 

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

from $305 / night

$2,134 / week

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avg. 1 hour 36 minutes

from $305 / night

6

Vacation private room in Windsor

Windsor and Maidenhead / Windsor

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Car not necessary
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 $159 / night

$1,030 / week

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from $159 / night

(5) 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 $212 / night

$1,485 / week

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from $212 / night

(1) Excellent 

16

Vacation apartment in Windsor

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 $259 / night

$1,809 / week

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Responds fast!
avg. 3 hours 15 minutes

from $259 / night

14

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 $159 / night

$1,054 - $1,127 / week

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avg. 3 hours 58 minutes

from $159 / night

(8) 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 $835 / night

$4,506 - $7,475 / week

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Responds fast!
avg. 3 hours 9 minutes

from $835 / 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). Sofa bed and two armchairs in the living room and dining table with four chairs. One bathroom with shower and tub very close to town centre yet tucked …see more

from $120 / night

$835 - $961 / week

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avg. 3 hours 58 minutes

from $120 / 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
Lovely two bedroom apartment sleeping 4 people in 2 beds. Fully fitted kitchen, two bedrooms, one bathroom and extra WC. Living room combined with kitchen and dining space. Balcony. Off street parking and walking distance to town centre (within 6 minutes). This is a fa …see more

from $133 / night

$862 - $928 / week

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Responds fast!
avg. 3 hours 58 minutes

from $133 / 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 $146 / night

$895 / week

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avg. 3 hours 58 minutes

from $146 / night

(11) 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 $259 / night

$2,485 - $2,783 / week

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Responds fast!
avg. 1 hour 3 minutes

from $259 / night