Houses in Windsor and Maidenhead and apartments – Holiday Lettings - Holiday Rentals Windsor and Maidenhead

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Windsor and Maidenhead

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65 Holiday homes

Travellers going to Windsor and Maidenhead are booking May dates now. Secure your holiday home today and have the perfect trip.

(12) Very Good 

45

Holiday 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 £120 / night

£840 - £1050 / week

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from £120 / night

20

Old Windsor holiday cottage rental

Windsor / Old Windsor

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Outside is a lovely garden, with Lutyens benches, a BBQ, and a Pergola /patio area with seating for 8+,  …see more

from £190 / night

£1575 / week

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from £190 / night

(5) Very Good 

26

Old Windsor holiday cottage rental

Windsor / Old Windsor

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly
“Gorgeous house on the river” We had a fantastic stay in this lovely house; all the rooms are very large and comfortable, with some great views over the river.  …see more

from £450 / night

£3000 - £3200 / week

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from £450 / night

(14) Excellent 

40

Holiday home in Windsor

Windsor and Maidenhead / Windsor

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Private garden
“Absolutely wonderful - full of charm and character” A really lovely cottage - bursting with 16th Century character and charm. Tastefully modernised and beautifully decorated - clearly by someone who knows what they are doing! Lots of interesting no  …see more

from £125 / night

£875 / week

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from £125 / night

(32) Excellent 

28

Holiday cottage in Windsor

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“Quality accommodation with high specification fitments” Only a mile or so from Junction 7 of the M4, this cottage has a rural feel tucked away with a small number of other properties. The accommodation has been delightfully decorated throughout with  …see more

from £105 / night

£735 / week

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from £105 / night

(4) Very Good 

22

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
9 The Courtyard is just steps from Windsor Castle and all the amenities of the town - yet it is situated in a secluded courtyard setting behind the High Street. Sleeping four people in comfort with secure private parking - although a car is not necessary.  …see more

from £85 / night

£595 - £780 / week

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from £85 / night

(8) Very Good 

24

Eton holiday apartment rental

Windsor / Eton

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
“Great flat in great location” Wonderfully appointed and homely flat in a wonderfully central location. Great restaurants, pubs and shops right on the doorstep and only a stones throw from the river. Can't ask for much more than that !  …see more

from £160 / night

£1120 / week

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from £160 / night

(6) Excellent 

18

Holiday 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
“Brilliant place to stay” We stayed in Windsor at Bridget and Tony's place. The home was beautiful, central to everything, the photos don't do it justice. we flew in from Australia that morning and came straight from Heathrow. It was an easy cab ride  …see more

from £150 / night

£1050 / week

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from £150 / night

(3) Excellent 

16

Windsor holiday 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
“Quite simply a delight” Liam the gentleman who owns the cottage, could not have done anymore for us on arrival and the cottage is every bit as good as it looks - a lovely week - "Thank you" David & Yvonne  …see more

from £79 / night

£550 - £660 / week

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from £79 / night

(1) Very Good 

13

Holiday home in Windsor

Windsor and Maidenhead / Windsor

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Charming two bedroom holiday cottage in Windsor. Double bedroom and second bed room with twin beds (pull out). Two sofas (one is a sofa bed) and dining table with four chairs. Walk to town in 3 minutes. Fully equipped kitchen. Small Patio area to rear.<br />Two be  …see more

from £119 / night

£700 - £850 / week

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from £119 / night

(12) Excellent 

24

Holiday cottage in Windsor

Windsor and Maidenhead / Windsor

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Private garden
Being once part of a 17th century farm the cottage has been recently refurbished but still retains its original character, the cottage has two bedrooms and a spacious open plan living area with a fully equipped Kitchen.  …see more

from £145 / night

£1120 - £1195 / week

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from £145 / night

12

Holiday 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.  …see more

from £125 / night

£599 - £850 / week

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from £125 / night

(1) Excellent 

8

Maidenhead Riverside holiday cottage rental

Maidenhead / Maidenhead Riverside

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Child friendly
  • Pet friendly
Modern, comfortable fully equipped one bedroom cottage. Suitable for short to medium term lets. Sleeps 2, (plus child on sofa bed). Tastefully converted stable, looking out onto fields and lakes. Off street parking, free wifi, laundry. Weekly service included in price.  …see more

from £75 / night

£525 - £1050 / week

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from £75 / night

(7) Excellent 

15

Apartment rental in Maidenhead Riverside with shared pool

Maidenhead / Maidenhead Riverside

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
New, spacious, sunny apartment in the leafy Riverside area of Maidenhead. Located in a quiet cul-de-sac, on the first floor, with Private Entrance and Off-street Parking. Ideal for runners and walkers, with direct access to the beautiful Thames Path. Walking distance  …see more

from £66 / night

£385 - £435 / week

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from £66 / night

(3) Very Good 

18

Eton holiday home rental

Windsor / Eton

3 5 3 nights min

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Car not necessary
“Perfect place to stay.” Stayed 16-19th August 2016. From booking to until we had to return home Bridget could not do enough for us. 2 adults and 2 children (8&9years old), house is absolutely fabulous. So well finished and comfortable. Location is per  …see more

from £150 / night

£1050 / week

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from £150 / night

30

Holiday home in Hurley

Maidenhead / Hurley

6 14 Min stay varies

  • 6 bedrooms
  • Sleeps 14
  • Min stay varies
  • Child friendly
Enjoy a family gathering or friends reunion in this beautiful stylish home. Equipped with all you could need for a special occasion. Situated in a pretty 'no through access' village with a wonderfully active community. The property has stunning gardens inclu  …see more

from £1200 / night

£3400 - £6250 / week

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from £1200 / night

(7) Excellent 

16

Windsor holiday apartment let

Windsor and Maidenhead / Windsor

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Car not necessary
  • Private garden
Ideal for short corporate lets, family holidays, visiting Windsor and surrounding area. Amazing riverside bars and restaurants.  …see more

from £100 / night

£660 - £1275 / week

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from £100 / night

(1) Very Good 

16

Holiday cottage in Maidenhead Riverside

Maidenhead / Maidenhead Riverside

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
Charming 2 bedroom cottage within grounds of Sheephouse Manor,16th century farmhouse. Sleeps up to 5, (3 adults and 2 children). Suitable for short to medium lets for professionals and families alike. Cosy and comfortable cottage for lets of 1 week or longer. Ideal loca  …see more

from £120 / night

£840 - £1400 / week

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from £120 / night

(37) Excellent 

23

Holiday studio in Windsor

Windsor and Maidenhead / Windsor

Studio 4 2 nights min

  • Studio
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Private garden
“Great stay!” We had a wonderful 3 days at the farm. We were given a very warm welcome by Angelica (and by the whole team, as we met them). We were also given useful tips for things to do during our stay. The kids loved the farm. They were up there  …see more

from £120 / night

£740 / week

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from £120 / night

(5) Excellent 

40

Holiday 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 £500 / night

£2450 - £4130 / week

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from £500 / night

(1) Excellent 

8

Holiday home in Cookham

Windsor and Maidenhead / Cookham

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Private garden
Our little chocolate box cottage is newly refurbished with an open plan living room and kitchen and an open fire. Cookham is a beautiful bustling typical English village with all the amenities and many lovely pubs and restaurants and easily accessible from London Paddin  …see more

from £125 / night

£750 / week

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from £125 / night

10

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Car not necessary
New 1 bedroom apartment located in central Windsor. Only two minutes walk away from Windsor Castle, The Long Walk and also Windsor's restaurants and shops or just a 10-minute travel to LegoLand! The apartment is 35m2 and consists of one double bedroom, open pla  …see more

from £89 / night

£623 / week

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from £89 / night

(15) Very Good 

13

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Car not necessary
“First class” Everything you could hope for, very glad I found it. The owner was most considerate and accommodating.  …see more

from £86 / night

£465 - £600 / week

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from £86 / night

6

Maidenhead holiday chalet rental

Windsor and Maidenhead / Maidenhead

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Child friendly
  • Pet friendly
Our studio chalet, offers a modern comfortable base for professionals and couples. If you are looking for short to medium term accommodation we are happy to help. Whether in between houses, moving into the area on business or on vacation, Cottage 1 has the answer. Off s  …see more

from £60 / night

£420 - £665 / week

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from £60 / night

(2) Average 

25

Home rental in Maidenhead

Windsor and Maidenhead / Maidenhead

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Maidenhead charming holiday rental house, traditional period English house, sleeps 6. Near Windsor, Eton, Henley, Marlow, Ascot, Legland, Thorpe ParkNear town center and train station.  …see more

from £90 / night

£630 / week

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from £90 / night

15

Holiday apartment in Windsor

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.  …see more

from £120 / night

£675 - £925 / week

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from £120 / night

(8) Excellent 

18

Holiday cottage in Holyport

Windsor and Maidenhead / Holyport

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Private garden
“Fantastic stay” We had a fantastic stay for 2 nights in Elaine's cottage. It's exactly as described and we had no hesitation in recommending the cottage to anyone else considering to stay there. We really liked the location and the village which had  …see more

from £105 / night

£845 - £920 / week

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from £105 / night

9

Holiday home in Maidenhead

Windsor and Maidenhead / Maidenhead

3 5 2 nights min

  • 3 bedrooms
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Private garden
This welcoming family home is close to the town centre and Maidenhead train station (both 10 minute walk), cinema, restaurants, shops, the leisure centre and supermarkets. You’ll love it here because of the fantastic location, the beautiful garden (including a gre  …see more

from £85 / night

£495 - £775 / week

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from £85 / night

21

Holiday home in Sunninghill

Ascot / Sunninghill

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Pet friendly
Beautiful 1886 Victorian Mansion set in five acres with heated swimming pool,tennis court,five a side ,basket ball,carp lake,decking,patio,parking for everybody. Baby grand piano,massive lawns ,electric gates,fabulous kitchen ,ice machine ,laundry,5 minute walk to Asco  …see more

from £699 / night

£4400 - £5000 / week

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from £699 / night

(5) Very Good 

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
Studio apartment with private walled garden available for business or holiday lets. There is plenty of parking adjacent to the apartment. Datchet is an attractive Thames-side village approximately 2 miles east of Windsor. Datchet railway station is on the Windsor to Wa  …see more

from £65 / night

£455 / week

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from £65 / 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 fo  …see more

from £162 / night

£1133 - £2003 / week

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from £162 / night

(5) Very Good 

10

Holiday apartment in Windsor

Windsor and Maidenhead / Windsor

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Child friendly
  • Ask about pets
Modern spacious 1 bedroom ground floor apartment, conveniently situated within 15/20mn walk to Windsor town centre. Close to Legoland, Windsor Racecourse and within 5mn walk to convenience store.  …see more

from £81 / night

£567 / week

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from £81 / night

9

Apartment rental in Windsor

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 £125 / night

£550 / week

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from £125 / night

6

Holiday home in Sunninghill

Ascot / Sunninghill

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
My new house has a purpose built SC wing for visiting family. It is situated in my lovely garden and close to supermarket 10 mins on foot, ditto mainline station, banks, restaurants etc. It had a mini kitchen, use of washing machine, sitting out or sitting in downs  …see more

from £180 / night

£720 / week

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from £180 / night

(2)  

7

Cottage rental in Maidenhead Riverside

Maidenhead / Maidenhead Riverside

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Clean, comfortable and modern and unique cottage. Sleeping 2 adults (and 1 child on a sofa bed). Available for stays of 1 week to 6 months. Pets accepted. Our one bedroom cottage is fully furnished with everything you need whether between properties, moving into the a  …see more

from £75 / night

£525 - £1050 / week

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from £75 / night

(2) Excellent 

11

Holiday home with golf nearby in Ascot

Windsor and Maidenhead / Ascot

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Car not necessary
  • Private garden
Secluded Luxury Property - set within idyllic golf course. Benefiting from use of the course and club house facilities, bar,sauna,restaurant and gym.5 bedrooms 2 ground floor bedrooms with en suites, 3 further bedrooms to first floor with a family bathroom.Entra  …see more

from £153 / night

£1071 - £1880 / week

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from £153 / night

15

Maidenhead holiday apartment rental

Windsor and Maidenhead / Maidenhead

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
Clean, comfortable and modern the three bedroom Wing of the Manor House, is completely self contained. Off street parking, private entrance with lobby. Downstairs ; fully equipped kitchen/lounge with sofa seating and large flat screen TV. Stairs to 3 bedrooms upstairs;  …see more

from £140 / night

£980 - £2100 / week

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from £140 / night

(37) Excellent 

24

Ascot holiday apartment rental

Windsor and Maidenhead / Ascot

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 110 km
  • Child friendly
  • Car not necessary
“A good nights sleep” Was fortunate enough to have to stay over a month so it began to feel like home. The appartment was comfortable, warm and very quiet so you could get a good nights sleep. Even though the second bedroom was a single we still manage  …see more

from £128 / night

£890 - £2000 / week

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from £128 / night

15

Holiday 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
Lovely two bedroom cottage, central Windsor, off-road parking. Two bedrooms (one double one twin), new bathroom, combined living/dining room, Fat screen TV, SKY TV. Enclosed patio garden.<br />Two bedroom cottage, central Windsor, parking. Sky TV, broadband, Short  …see more

from £95 / night

£650 - £825 / week

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from £95 / night

(1) Very Good 

11

Home rental in Windsor

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 £260 / night

£1820 / week

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from £260 / night

Top Destination reviews

The Old Wharf Cottage - Riverside Living
Great house for friends/family gatherings

Lovely spacious house, in a quiet road overlooking the river. Short walk to Wraysbury (pretty village) and Windsor a short drive away. The house was quirky and full of charm, as well as clean, modern and well equipped. The sun room at the back overlo … see more
Beautiful detached family home 10 mins to Legoland
Excellent house absolutely ideal for a visit to Legoland.

The house was excellent... great facilities...comfortable.... well equipped ...ideal for us with our three small grandchildren. It actually exceeded our expectations and we would certainly recommend it to others. Justina was so helpful and we appreci … see more
Windsor Town Centre -Serviced Cottage
Quite simply a delight

Liam the gentleman who owns the cottage, could not have done anymore for us on arrival and the cottage is every bit as good as it looks - a lovely week - "Thank you" David & Yvonne … see more
Windsor Garden Studio. Only 5 minutes from Legoland, Lapland UK & town centre.
Wonderful place to stay

Have just stayed here for three nights and would recommend to anybody. It's lovely and has everything you need and a welcome basket is left for you with milk in fridge also. An excellent idea and there is nothing the owners have not thought of. Very … see more
Eton/Windsor
Perfect place to stay.

Stayed 16-19th August 2016. From booking to until we had to return home Bridget could not do enough for us. 2 adults and 2 children (8&9years old), house is absolutely fabulous. So well finished and comfortable. Location is perfect, ideally situated … see more
Windsor/Eton 2 Bedroom apartment Central location
An exceptional property. Great location!!!

We had a lovely weeks stay in Eton. Close to Windsor, with a view of the castle. Lovely restaurants on the river, close to trains, shops & cafes. A lovely, romantic stay. A lovely, comfortable bed. Owner lovely. We will return!! … see more