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

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824 Holiday homes

Holiday apartment in Windsor

Windsor apartment

3 bedrooms • 2 bathrooms • sleeps 6

2 reviews

from £195 / night

£1,363 / week

1 / 19

Holiday home in Windsor

Windsor house

2 bedrooms • 1 bathroom • sleeps 4

1 review

from £126 / night

£882 / week

1 / 21

Old Windsor holiday cottage rental

Old Windsor cottage

5 bedrooms • 4 bathrooms • sleeps 10

14 reviews

from £630 / night

£4,122 - £6,584 / week

1 / 46

Eton holiday home rental

Eton house

2 bedrooms • 1 bathroom • sleeps 4

4 reviews

from £205 / night

£1,435 / week

1 / 13

Home rental in Sunningdale

Sunningdale house

5 bedrooms • 4 bathrooms • sleeps 12

3 reviews

from £458 / night

£3,206 / week

1 / 16

Maidenhead Riverside holiday cottage rental

Maidenhead Riverside cottage

1 bedroom • 1 bathroom • sleeps 3

1 review

from £103 / night

£722 / week

1 / 8

Maidenhead holiday home rental

Maidenhead house

2 bedrooms • 1 bathroom • sleeps 4

1 review

from £172 / night

£1,203 / week

1 / 23

Holiday apartment rental

Windsor apartment

2 bedrooms • 3 bathrooms • sleeps 6

1 review

from £258 / night

£1,804 / week

1 / 4

Apartment rental in Windsor

Windsor apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £138 / night

£962 / week

1 / 18

Apartment rental in Windsor

Windsor apartment

2 bedrooms • 2 bathrooms • sleeps 6

3 reviews

from £241 / night

£1,684 / week

1 / 19

Home rental in Windsor with golf nearby

Windsor house

4 bedrooms • 3 bathrooms • sleeps 7

5 reviews

from £492 / night

£3,440 / week

1 / 54

Holiday apartment with golf nearby in Ascot

Ascot apartment

3 bedrooms • 2 bathrooms • sleeps 6

2 reviews

from £149 / night

£1,043 / week

1 / 11

Studio rental in Old Windsor

Old Windsor studio

Studio • 1 bathroom • sleeps 4

5 reviews

from £207 / night

£1,443 / week

1 / 30

Windsor holiday apartment rental

Windsor apartment

2 bedrooms • 3 bathrooms • sleeps 4

from £102 / night

£682 / week

1 / 23

Windsor holiday apartment rental

Windsor apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £224 / night

£1,563 / week

1 / 16

Holiday home with golf nearby in Wraysbury

Wraysbury house

4 bedrooms • 3 bathrooms • sleeps 10

6 reviews

from £401 / night

£2,519 / week

1 / 33

Old Windsor holiday studio rental

Old Windsor studio

Studio • 1 bathroom • sleeps 2

3 reviews

from £92 / night

£573 / week

1 / 14

Holiday b&b rental

Windsor b&b

3 bedrooms • 3 bathrooms • sleeps 6

2 reviews

from £213 / night

£1,489 / week

1 / 12

Holiday apartment in Windsor

Windsor apartment

2 bedrooms • 1 bathroom • sleeps 4

8 reviews

from £144 / night

£916 - £1,002 / week

1 / 18

Studio rental in Windsor with golf nearby

Windsor studio

Studio • 1 bathroom • sleeps 2

6 reviews

from £92 / night

£642 / week

1 / 12

Eton holiday apartment rental

Eton apartment

2 bedrooms • 1 bathroom • sleeps 5

17 reviews

from £171 / night

£1,195 / week

1 / 23

Holiday apartment rental

Windsor apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £138 / night

£882 / week

1 / 16

Holiday studio in Windsor

Windsor studio

Studio • 1 bathroom • sleeps 4

“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 friendly and feels like you are at home. Brilliant location. We went to Legoland and its literally ten mins away. We got a taxi into Windsor to see the castle and was only eight pounds which is cheaper than parking. Had a lovely stay and will not hesitate to go back again.

41 reviews

from £260 / night

£1,820 / week

1 / 24

Holiday apartment in Windsor

Windsor apartment

2 bedrooms • 3 bathrooms • sleeps 6

3 reviews

from £224 / night

£1,563 / week

1 / 16

Maidenhead holiday chalet rental

Maidenhead chalet

1 bedroom • 1 bathroom • sleeps 2

from £98 / night

£682 / week

1 / 7

Apartment rental in Maidenhead

Maidenhead apartment

1 bedroom • 1 bathroom • sleeps 3

1 review

from £86 / night

£602 / week

1 / 12

Old Windsor holiday cottage rental

Old Windsor cottage

3 bedrooms • 2 bathrooms • sleeps 7

9 reviews

from £321 / night

£2,245 / week

1 / 33

Windsor holiday lodge rental

Windsor lodge

2 bedrooms • 1 bathroom • sleeps 5

17 reviews

from £283 / night

£1,980 / week

1 / 26

Windsor holiday apartment rental

Windsor apartment

1 bedroom • 1 bathroom • sleeps 3

2 reviews

from £103 / night

£610 - £730 / week

1 / 13

Maidenhead holiday apartment rental

Maidenhead apartment

3 bedrooms • 3 bathrooms • sleeps 6

from £195 / night

£1,361 / week

1 / 15

Holiday home with golf nearby in Ascot

Ascot house

5 bedrooms • 3 bathrooms • sleeps 8

4 reviews

from £269 / night

£1,880 / week

1 / 13

Ascot holiday apartment rental

Ascot apartment

2 bedrooms • 2 bathrooms • sleeps 4

41 reviews

from £128 / night

£890 / week

1 / 24

Holiday apartment in Maidenhead

Maidenhead apartment

1 bedroom • 1 bathroom • sleeps 3

from £103 / night

£722 / week

1 / 9

Holiday home rental

Windsor house

4 bedrooms • 3 bathrooms • sleeps 7

1 review

from £294 / night

£2,052 / week

1 / 55

Holiday private room in Windsor

Windsor private room

2 bedrooms • 1 bathroom • sleeps 4

from £132 / night

£802 - £1,123 / week

1 / 7

Holiday studio in Windsor

Windsor studio

Studio • 1 bathroom • sleeps 4

16 reviews

from £226 / night

£1,579 / week

1 / 21

Holiday home in Old Windsor

Old Windsor house

4 bedrooms • 3 bathrooms • sleeps 7

3 reviews

from £573 / night

£4,008 / week

1 / 51

Holiday apartment letting

Windsor apartment

1 bedroom • 1 bathroom • sleeps 4

2 reviews

from £226 / night

£1,579 / week

1 / 14

Apartment rental in Windsor

Windsor apartment

1 bedroom • 1 bathroom • sleeps 4

from £98 / night

£682 / week

1 / 19

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Top Destination reviews

Manor Cottage B&B
Affable Hosts and a comfortable accommodation.

We enjoyed our stay in Old Windsor largely because of the kindness of our hosts. Their home is beautiful and clean and they serve a wonderful breakfast. On-site parking was a plus. Close to restaurants and shops, Manor Cottage is well located. It is a short drive to the castle but a car is recommended,see more
9 The Courtyard, Windsor
Easy going holidays

Excelent service and posission with private parking bay. Approachable owner. Very clean flat wiht many usefull futures. Recomented … see more
Central Windsor Apartment Facing The Castle
Excellent apartment beware of the stairs

The apartment itself was very well appointed and very clesn. It's location was excellent. However, there was no mention of the many steps to get to it and when travelling with two eighty year olds, one with a pacemaker, this was a drawback. Also the stairs inside the apartment were very steep and narrow. This aside, Jeremy was extremely helpful, finding us an extra parking space nearby as we had two cars. Would use the apartment again but would warn anyone else of the stairs.see more
Hampden Apartments - The Victoria
Beautiful, clean, modern apartment close to the centre of town

Jeremy's apartment is a lovely place to stay for Windsor or Ascot. We had a wonderful stay. The apartment is clean, modern and has everything you need. Jeremy was really helpful before our stay in confirming the presence of a few items in the apartment which was great. There is parking (although spaces quite tight if you have a large car) which was a bonus. Would definitely stay again and highly recommend!see more
Gorgeous Country Cottage beside Windsor Great Park & overlooking Windsor Castle
Lovely Rural Cottage

The lovely Victorian lodge was beautifully appointed and immaculate and provided our family with a great week’s holiday base for enjoying the sights of Windsor. A short walk from Great Windsor Park where we spent time every day. Just as nice to stay at home and enjoy the rural views, garden and outdoor dining setting. Hamish was a great host and knowledgeable about the area.see more
Welcome to our Boutique Sensory Bijoux Garden Studio.A truly sensory experience!
Funky and unique

Really enjoyed staying at this air b n b . The host is the best and puts you her priority. Communication is swift and you can tell she's a genuinely nice person. The accommodation was sooo funky , modern and fully equipped to have a break. I'd say its aimed more towards the younger generation and those into design,as the host has huge amount of effort into interiors and lighting. It's very cool and nice and private. A real pad . Highly recommended .see more

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