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Windsor and Maidenhead Holiday Rentals

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Our top choices for Windsor and Maidenhead holiday rentals

A modern house with a dark exterior, a patio with outdoor furniture, and a white umbrella.

1. Willow Court Farm

Willow Court Farm
4.0 star property
Windsor
10.0 out of 10, Exceptional, (217 reviews)
"Very nice, comfortable room, nice to have the kitchen. Lots of space outside to eat and relax! The kids loved the animals and that it’s clise to Legoland! The restaurant near by was really nice too and also easy to get around without a car."
Canada
Anne
The price is HK$1,465
HK$1,758 total
includes taxes & fees
15 Oct - 16 Oct
Willow Court Farm
A cozy living room with a green sofa, a decorative tapestry, and a high ceiling with exposed beams.

2. Copper Castle & Petting Farm near Legoland

Copper Castle & Petting Farm near Legoland
4.0 star property
Windsor
10.0 out of 10, Exceptional, (5 reviews)
"The copper castle was an amazing place to stay, clean, comfortable, staff were amazing, children loved the animals and collecting egg's from the chickens in the morning. Owner's were very helpful and accommodating, will definitely be coming back for another stay."
United Kingdom
Susan
The price is HK$1,430
HK$1,716 total
includes taxes & fees
16 Oct - 17 Oct
Copper Castle & Petting Farm near Legoland
A white door with a sign reading "Cavendish House" and a fire access sign above it.

3. Cavendish House

Cavendish House
5.0 star property
Windsor City Centre
9.8 out of 10, Exceptional, (80 reviews)
Cavendish House
A modern kitchen with a central island, two bar stools, a stainless steel range hood, and a window with blinds.

4. Hampden Apartments - The William

Hampden Apartments - The William
3.0 star property
Eton
9.2 out of 10, Wonderful, (21 reviews)
"Always a lovely place to stay "
United Kingdom
Tony
Hampden Apartments - The William
A neatly made bed with two pillows, a bedside table with a lamp, and a bedside table with a decorative item.

5. The Fox at Hurley - Delightful Property!

The Fox at Hurley - Delightful Property!
Maidenhead
The price is HK$643
HK$1,523 total
includes taxes & fees
19 Oct - 20 Oct
The Fox at Hurley - Delightful Property!
A bedroom with a bed, a dresser, a window, and a chandelier.

6. Spacious, light apartment sleeps up to four

Spacious, light apartment sleeps up to four
Cookham
9.6 out of 10, Exceptional, (19 reviews)
"Beautifully refurbished property with very helpful hosts."
United Kingdom
Alexandra C.
The price is HK$1,026
HK$2,187 total
includes taxes & fees
17 Oct - 18 Oct
Spacious, light apartment sleeps up to four
A spacious living room with a dark sofa, a wooden coffee table, and a patterned rug.

7. Luxury 2 Bedroom Apartment

Luxury 2 Bedroom Apartment
Clewer North
The price is HK$1,082
HK$2,067 total
includes taxes & fees
16 Oct - 17 Oct
Luxury 2 Bedroom Apartment
A modern living room with a flat-screen TV, a sofa, and a coffee table. There is a kitchen area with a dining table and bar stools.

8. Hampden Apartments - The George

Hampden Apartments - The George
4.0 star property
Windsor City Centre
9.2 out of 10, Wonderful, (37 reviews)
"Amazing location, walking distance to shops, restaurants, the theatre and of course the castle. The apartment was clean on arrival and had everything we needed for our stay. "
United Kingdom
Alison
The price is HK$2,099
HK$2,099 total
includes taxes & fees
21 Oct - 22 Oct
Hampden Apartments - The George
A historic building with a central courtyard, a fountain, and a clock tower.

9. Character Victorian apartment close to Windsor town with secure parking

Character Victorian apartment close to Windsor town with secure parking
Clewer East
8.8 out of 10, Excellent, (3 reviews)
"A gorgeous opulent place to stay while in Windsor. We appreciated the extra touches like the fresh milk for tea!"
Canada
Isabel
The price is HK$1,847
HK$2,230 total
includes taxes & fees
15 Oct - 16 Oct
Character Victorian apartment close to Windsor town with secure parking
A modern house with a patio, a garden with various plants, and a wooden deck.

10. Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
3.0 star property
Wraysbury
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,978
HK$2,684 total
includes taxes & fees
15 Oct - 16 Oct
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
A narrow wooden pathway leading to a building with a checkered floor.

11. Lovely cottage in the heart of the picturesque village of Cookham

Lovely cottage in the heart of the picturesque village of Cookham
Cookham
10.0 out of 10, Exceptional, (1 review)
"Roseleigh Cottage is a lovely little house. It is ideally situated in central Cookham a stones throw from the Thames tow path and close to a range of pubs and other places to eat. The cottage is very well equipped and comfortable. We really enjoyed our stay as did our dog who appreciated the many walks thereabouts."
United States
Maggie L.
The price is HK$1,632
HK$2,451 total
includes taxes & fees
15 Oct - 16 Oct
Lovely cottage in the heart of the picturesque village of Cookham
A balcony with a white chair, a small table, and a floor lamp.

12. Charming 1BR Apartment | Parking Included

Charming 1BR Apartment | Parking Included
Windsor City Centre
The price is HK$1,571
HK$2,351 total
includes taxes & fees
28 Oct - 29 Oct
Charming 1BR Apartment | Parking Included
A modern kitchen with a wooden countertop, a grey sofa, and a blue accent wall.

13. Windsor Home with Free Parking

Windsor Home with Free Parking
Clewer South
10.0 out of 10, Exceptional, (1 review)
"A perfect location for visiting Legoland and Windsor Castle. Easy to find, parking is literally right outside of the front door and the apartment is fitted with everything you could need.We will definitely recommend and will use again if we visit Legoland again in the future."
United Kingdom
Ian G.
The price is HK$1,295
HK$1,783 total
includes taxes & fees
17 Oct - 18 Oct
Windsor Home with Free Parking
A modern house with a patio, a garden with various plants, and a wooden deck.

14. Relaxing guest house with Jacuzzi & boat hire

Relaxing guest house with Jacuzzi & boat hire
Wraysbury
10.0 out of 10, Exceptional, (18 reviews)
"We had a lovely stay! The hot tub was fantastic, and the boat was absolutely fabulous. We really enjoyed ourselves and had a wonderful time. Thank you for a great stay!"
United Kingdom
Chaim
The price is HK$2,369
HK$2,628 total
includes taxes & fees
15 Oct - 16 Oct
Relaxing guest house with Jacuzzi & boat hire
A cozy bedroom with a large bed, a grey sofa, a patterned rug, a window with curtains, and a fireplace.

15. Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish

Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
Windsor City Centre
8.0 out of 10, Very good, (4 reviews)
"Great house. Perfect location. A wonderful stay."
United States
David T.
The price is HK$1,492
HK$2,415 total
includes taxes & fees
1 Nov - 2 Nov
Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
A cozy interior with striped sofas, a kitchen area, and a bed with a view.

16. Shepherds Hut with Hot Tub Retreat - By Tempstay

Shepherds Hut with Hot Tub Retreat - By Tempstay
White Waltham
Shepherds Hut with Hot Tub Retreat - By Tempstay
A modern kitchen with a blue accent wall, wooden staircase, and a dining area with a table set for four.

17. Heartwarming Windsor Cottage with Free Parking

Heartwarming Windsor Cottage with Free Parking
Clewer East
10.0 out of 10, Exceptional, (1 review)
The price is HK$1,364
HK$2,248 total
includes taxes & fees
16 Oct - 17 Oct
Heartwarming Windsor Cottage with Free Parking
A modern living room with a grey sofa, a glass coffee table with orange juice, and a large window with a view of stone buildings.

18. Central Apartment Facing Windsor Castle

Central Apartment Facing Windsor Castle
4.0 star property
Windsor City Centre
8.6 out of 10, Excellent, (31 reviews)
"Amazing location, lots of shops !! "
United States
Samantha
Central Apartment Facing Windsor Castle
A bedroom with a window, a bed with pillows, and a lamp.

19. Ascot Racecourse Apartment

Ascot Racecourse Apartment
Ascot
The price is HK$1,026
HK$1,606 total
includes taxes & fees
26 Oct - 27 Oct
Ascot Racecourse Apartment
A modern living room with a flat-screen TV mounted on a wooden wall, a window with curtains, a wooden bench, and a framed picture on the wall.

20. Elegant Windsor Flat -Short Walk to Windsor Castle, River Thames &Train Station

Elegant Windsor Flat -Short Walk to Windsor Castle, River Thames &Train Station
Eton
10.0 out of 10, Exceptional, (3 reviews)
"Gorgeous flat in a perfect location. There were so great places to walk to, including Windsor Castle. Highly recommend this place!"
United States
jennifer j.
The price is HK$1,716
HK$1,966 total
includes taxes & fees
15 Oct - 16 Oct
Elegant Windsor Flat -Short Walk to Windsor Castle, River Thames &Train Station
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Windsor and Maidenhead Hotel Reviews

Macdonald Compleat Angler

Macdonald Compleat Angler

10/10 Excellent
"The staff were all very friendly and helpful. Very pleasant stay."
Julie 1-night trip
Posted 11 hours ago
Macdonald Compleat Angler