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Holiday Rentals in Windsor and Maidenhead

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Our top choices for Windsor and Maidenhead holiday rentals

A modern building with dark siding, a glass door entrance, and two potted plants.

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 €174
includes taxes & fees
11 Nov - 12 Nov
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)
"Fantastic accommodation and setting. We loved our stay in the copper castle. The hosts have thought of everything to make your stay as enjoyable as possible and the goats outside the accommodation are very friendly!"
United Kingdom
HAYLEY
The price is €192
includes taxes & fees
11 Nov - 12 Nov
Copper Castle & Petting Farm near Legoland
A bedroom with a bed, a dresser, a window, and a chandelier.

3. 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 €242
includes taxes & fees
19 Nov - 20 Nov
Spacious, light apartment sleeps up to four
A spacious living room with a dark sofa, a wooden coffee table, and a patterned rug.

4. Luxury 2 Bedroom Apartment

Luxury 2 Bedroom Apartment
Clewer North
The price is €264
includes taxes & fees
15 Nov - 16 Nov
Luxury 2 Bedroom Apartment
A narrow wooden pathway leading to a building with a checkered floor.

5. 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 €260
includes taxes & fees
11 Nov - 12 Nov
Lovely cottage in the heart of the picturesque village of Cookham
A modern kitchen with a central island, two bar stools, a stainless steel range hood, and a window with blinds.

6. Hampden Apartments - The William

Hampden Apartments - The William
3.0 star property
Eton
9.2 out of 10, Wonderful, (23 reviews)
"Always a lovely place to stay "
United Kingdom
Tony
The price is €159
includes taxes & fees
15 Nov - 16 Nov
Hampden Apartments - The William
A historic building with a central courtyard, a fountain, and a clock tower.

7. 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 €276
includes taxes & fees
10 Dec - 11 Dec
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.

8. 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 €304
includes taxes & fees
11 Nov - 12 Nov
Relaxing guest house with Jacuzzi & boat hire
A modern house with a patio, a garden with various plants, and a wooden deck.

9. 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 €310
includes taxes & fees
21 Nov - 22 Nov
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
A cozy interior with striped sofas, a kitchen area, and a bed with a view.

10. Shepherds Hut with Hot Tub Retreat - By Tempstay

Shepherds Hut with Hot Tub Retreat - By Tempstay
White Waltham
The price is €324
includes taxes & fees
11 Nov - 12 Nov
Shepherds Hut with Hot Tub Retreat - By Tempstay
A round table with a clear glass, a white bowl, a vase with white flowers, and a candle in the background.

11. Ascot Racecourse Apartment

Ascot Racecourse Apartment
Ascot
The price is €183
includes taxes & fees
10 Dec - 11 Dec
Ascot Racecourse Apartment
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 €237
includes taxes & fees
6 Dec - 7 Dec
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 €199
includes taxes & fees
12 Nov - 13 Nov
Windsor Home with Free Parking
A bedroom with a large bed, two bedside tables, a tray with breakfast, and a view of the sea through the window.

14. Hampden Apartments - The Henry

Hampden Apartments - The Henry
4.0 star property
Windsor City Centre
9.0 out of 10, Wonderful, (23 reviews)
"Superb apartment very good location far enough away from noise close enough to walk to centre. Apartment could fo with a little TLC. To bring back up to superb throughout. Overall a great stay"
United Kingdom
Dave
The price is €222
includes taxes & fees
15 Nov - 16 Nov
Hampden Apartments - The Henry
A modern kitchen with a blue accent wall, wooden staircase, and a dining area with a table set for four.

15. Heartwarming Windsor Cottage with Free Parking

Heartwarming Windsor Cottage with Free Parking
Clewer East
10.0 out of 10, Exceptional, (1 review)
"Beautiful place to stay."
United States
Anonymous traveller
The price is €267
includes taxes & fees
11 Nov - 12 Nov
Heartwarming Windsor Cottage with Free Parking
A living room with a sofa, a television, and a view of a church through a large window.

16. Stylish 2 Bed Flat, 2 min walk to Windsor Castle

Stylish 2 Bed Flat, 2 min walk to Windsor Castle
Windsor City Centre
Stylish 2 Bed Flat, 2 min walk to Windsor Castle
A cozy bedroom with a large bed, a grey sofa, a patterned rug, a window with curtains, and a fireplace.

17. 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 €239
includes taxes & fees
11 Nov - 12 Nov
Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
A modern living room with a grey sofa, a dining table with chairs, and a large window with shelves.

18. Your Windsor Retreat | 1Bed/1Bath + Free Parking

Your Windsor Retreat | 1Bed/1Bath + Free Parking
Windsor City Centre
8.0 out of 10, Very good, (2 reviews)
"We had a lovely time and found the flat was was in a great area and clean and suited us perfectly!"
Australia
Toni
Your Windsor Retreat | 1Bed/1Bath + Free Parking
A room with two beds, a large screen displaying a streaming service interface, and a window with a view of the outside.

19. Windsor Luxe Living – 3BR Near Windsor Castle

Windsor Luxe Living – 3BR Near Windsor Castle
Clewer East
2.0 out of 10, (2 reviews)
"Could not get into the property. There was a number on the door for WhatsApp messages. Landlord claimed they no longer take bookings. Belvilla, the booking operator has been less than helpful in getting the cost refunded"
United Kingdom
Rupert
The price is €215
includes taxes & fees
11 Nov - 12 Nov
Windsor Luxe Living – 3BR Near Windsor Castle
A living room with a fireplace, sofa, and dining area.

20. Stylish 2-Bed Apartment in the Heart of Windsor – Walk to Windsor Castle

Stylish 2-Bed Apartment in the Heart of Windsor – Walk to Windsor Castle
Windsor City Centre
8.0 out of 10, Very good, (1 review)
"Great location, clean, the only fault in the listing is the steps in the apartment. There was great communication with the host."
United States
Sue G.
The price is €223
includes taxes & fees
11 Nov - 12 Nov
Stylish 2-Bed Apartment in the Heart of Windsor – Walk to Windsor Castle
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

LEGOLAND Windsor Resort

LEGOLAND Windsor Resort

10/10 Excellent
"We stayed at Legoland for the first time, the room was basic and clean but could have been bit cleaner. the bed are comfy and having a separate area for son to sleep was great. they have a bit of Lego for them to play with, which is nice. they have a small activity for them to do and them do and find a gift in the safe. We used the pool which was ok. was a bit colder then I expected and very slippery so be careful, lots of kids running around and jumping in so be mindful of younger kids. Lego playroom was amazing my son and us had a great time in their. Lego is both dirty but it's probably impossible to keep clean so make sure you take wipes to wash kids hands. We had breakfast at bricks restaurant and this was ok. was nice that they kids could plate up themselves."
Kajal 1-night trip
Posted less than an hour ago
LEGOLAND Windsor Resort

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