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Windsor and Maidenhead Holiday Rentals

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Our top choices for Windsor and Maidenhead holiday rentals

Exterior detail

1. Willow Court Farm

Willow Court Farm
4.0 star property
Windsor
10.0 out of 10, Exceptional, (213 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 AU$337
includes taxes & fees
8 Sept - 9 Sept
Willow Court Farm
Deluxe Apartment | Private kitchen

2. Hampden Apartments - The Louis

Hampden Apartments - The Louis
3.0 star property
Eton
9.8 out of 10, Exceptional, (13 reviews)
"Great location especially having free parking. The apartment was very clean and modern."
United Kingdom
Lucy
Hampden Apartments - The Louis
Deluxe Cabin, Garden View

3. Copper Castle & Petting Farm near Legoland

Copper Castle & Petting Farm near Legoland
4.0 star property
Windsor
10.0 out of 10, Exceptional, (4 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 AU$355
includes taxes & fees
11 Sept - 12 Sept
Copper Castle & Petting Farm near Legoland
1 bedroom, iron/ironing board, WiFi, bed sheets

4. The Fox at Hurley - Delightful Property!

The Fox at Hurley - Delightful Property!
Maidenhead
The price is AU$278
includes taxes & fees
4 Oct - 5 Oct
The Fox at Hurley - Delightful Property!
TV

5. Luxury 2 Bedroom Apartment

Luxury 2 Bedroom Apartment
Clewer North
The price is AU$362
includes taxes & fees
14 Sept - 15 Sept
Luxury 2 Bedroom Apartment
Deluxe Apartment | Private kitchen

6. Hampden Apartments - The William

Hampden Apartments - The William
3.0 star property
Eton
9.0 out of 10, Wonderful, (19 reviews)
"Fantastic location and spotlessly clean. We really enjoyed our stay "
United Kingdom
Ian
The price is AU$273
includes taxes & fees
17 Sept - 18 Sept
Hampden Apartments - The William
2 bedrooms, desk, iron/ironing board, free WiFi

7. 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 AU$391
includes taxes & fees
8 Sept - 9 Sept
Spacious, light apartment sleeps up to four
Interior

8. A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
Old Windsor
9.4 out of 10, Exceptional, (10 reviews)
"Lovely Cabin"
United Kingdom
John W.
The price is AU$244
includes taxes & fees
9 Sept - 10 Sept
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.
Interior

9. 1BR|Parking|Doorstep Of Windsor Castle|By Tempstay

1BR|Parking|Doorstep Of Windsor Castle|By Tempstay
Windsor City Centre
9.6 out of 10, Exceptional, (7 reviews)
"Great place to stay for visiting the castle and surrounding areas with the bonus of a parking space.Place was very clean and warm with plenty of bars and restaurants minutes away. Would definitely go back."
United Kingdom
Richard J.
The price is AU$363
includes taxes & fees
8 Sept - 9 Sept
1BR|Parking|Doorstep Of Windsor Castle|By Tempstay
2 bedrooms, iron/ironing board, WiFi, bed sheets

10. Spacious Apartment with Private Garden By Tempstay

Spacious Apartment with Private Garden By Tempstay
Windsor City Centre
8.6 out of 10, Excellent, (4 reviews)
"I traveled to Windsor with my husband and 17 year old daughter. This apartment has a good layout with two separate bedrooms and is within walking distance of train station, shops, restaurants and the castle. We had a great stay."
United States
Sherry N.
The price is AU$424
includes taxes & fees
8 Sept - 9 Sept
Spacious Apartment with Private Garden By Tempstay
Comfort Apartment, 2 Bedrooms, Non Smoking

11. 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 AU$363
includes taxes & fees
28 Sept - 29 Sept
Hampden Apartments - The George
Deluxe Apartment

12. Hampden Apartments - The Edward

Hampden Apartments - The Edward
3.5 star property
Windsor City Centre
7.8 out of 10, Good, (7 reviews)
"Enjoyed the stay "
United Kingdom
david
The price is AU$262
includes taxes & fees
13 Sept - 14 Sept
Hampden Apartments - The Edward
2 bedrooms, iron/ironing board, WiFi, bed sheets

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

Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
Windsor City Centre
9.4 out of 10, Exceptional, (3 reviews)
"Delightful, charming flat on a quiet road right next to everything you want to see in Windsor."
United States
Jesse
The price is AU$428
includes taxes & fees
1 Oct - 2 Oct
Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish
Apartment, 3 Bedrooms

14. Hampden Apartments - The Henry

Hampden Apartments - The Henry
4.0 star property
Windsor City Centre
9.0 out of 10, Wonderful, (22 reviews)
"Loved our stay great location. Apartment was clean and prepared for our visit. The property could use a few repairs but altogether it was a great place to stay. "
United States
Jeremy
Hampden Apartments - The Henry
Deluxe House | Private kitchen

15. Fabulous Central Windsor Town House

Fabulous Central Windsor Town House
3.0 star property
Windsor City Centre
10.0 out of 10, Exceptional, (1 review)
"House is exactly as in the pictures. Lovely, spacious and clean. Kids loved the bunk bed. "
United Kingdom
Abdullah
The price is AU$562
includes taxes & fees
13 Sept - 14 Sept
Fabulous Central Windsor Town House
1 bedroom, iron/ironing board, travel cot, WiFi

16. 1BR Gem, Private Parking - VAT Q - By Tempstay

1BR Gem, Private Parking - VAT Q - By Tempstay
Clewer East
10.0 out of 10, Exceptional, (1 review)
"Lovely unit, although the check in process was a little difficult, an all automatic code system, which is fine for younger people. The system seemed to be a little temperamental. However, we enjoyed our stay, parking was a plus. Everything we needed was available. It was a walk to a supermarket."
United States
Anne J.
1BR Gem, Private Parking - VAT Q - By Tempstay
Cabin | Property grounds

17. 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 AU$486
includes taxes & fees
9 Sept - 10 Sept
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
TV

18. Windsor Gem: 1 Bed|1 Bath| Free Parking

Windsor Gem: 1 Bed|1 Bath| Free Parking
Windsor City Centre
10.0 out of 10, Exceptional, (1 review)
"Great looking apartment. "
United States
Michelle P.
The price is AU$439
includes taxes & fees
20 Sept - 21 Sept
Windsor Gem: 1 Bed|1 Bath| Free Parking
1 bedroom, iron/ironing board, WiFi, bed sheets

19. 1BR Apartment | Walk to Shops & Castle

1BR Apartment | Walk to Shops & Castle
Windsor City Centre
8.8 out of 10, Excellent, (3 reviews)
"It was very nice, clean and local to town. It was just a bit smaller than we were expecting but the property itself was lovely and everything worked and there was a supply of tea,coffee and milk, shower wash, hand soaps. Would recommend. "
United Kingdom
Paula B.
The price is AU$300
includes taxes & fees
23 Sept - 24 Sept
1BR Apartment | Walk to Shops & Castle
Smart TV

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 AU$304
includes taxes & fees
10 Sept - 11 Sept
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

De Vere Beaumont Estate

De Vere Beaumont Estate

10/10 Excellent
"So much to see around the hotel.. hotel reception could’ve briefed us prior attendance. But overall great!"
Salauddin 1-night trip
Posted 6 hours ago
De Vere Beaumont Estate

Find out more about Windsor and Maidenhead

Everything you need to know about Windsor and Maidenhead holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor and Maidenhead holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor and Maidenhead holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Windsor and Maidenhead holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Windsor and Maidenhead. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor and Maidenhead holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Windsor and Maidenhead holiday rentals we have chosen for you start as low as AU$244 per night. Entering your travel dates in the search wizard you might find even better deals.

How to find incredible deals on Windsor and Maidenhead rentals

At Expedia, we put the best Windsor and Maidenhead holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Windsor and Maidenhead rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor and Maidenhead holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor and Maidenhead. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.