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Our top choices for Windsor and Maidenhead holiday rentals

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 £138
includes taxes & fees
11 Nov - 12 Nov
Willow Court Farm

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 £157
includes taxes & fees
12 Nov - 13 Nov
Copper Castle & Petting Farm near Legoland

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 £192
includes taxes & fees
11 Nov - 12 Nov
Spacious, light apartment sleeps up to four

4. Luxury 2 Bedroom Apartment

Luxury 2 Bedroom Apartment
Clewer North
The price is £220
includes taxes & fees
15 Nov - 16 Nov
Luxury 2 Bedroom Apartment

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 £217
includes taxes & fees
11 Nov - 12 Nov
Lovely cottage in the heart of the picturesque village of Cookham

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 £133
includes taxes & fees
15 Nov - 16 Nov
Hampden Apartments - The William

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 £207
includes taxes & fees
11 Nov - 12 Nov
Character Victorian apartment close to Windsor town with secure parking

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 £254
includes taxes & fees
11 Nov - 12 Nov
Relaxing guest house with Jacuzzi & boat hire

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 £259
includes taxes & fees
12 Nov - 13 Nov
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

10. Shepherds Hut with Hot Tub Retreat - By Tempstay

Shepherds Hut with Hot Tub Retreat - By Tempstay
White Waltham
The price is £271
includes taxes & fees
11 Nov - 12 Nov
Shepherds Hut with Hot Tub Retreat - By Tempstay

11. Ascot Racecourse Apartment

Ascot Racecourse Apartment
Ascot
The price is £153
includes taxes & fees
11 Nov - 12 Nov
Ascot Racecourse Apartment

12. Charming 1BR Apartment | Parking Included

Charming 1BR Apartment | Parking Included
Windsor City Centre
The price is £198
includes taxes & fees
6 Dec - 7 Dec
Charming 1BR Apartment | Parking Included

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 £166
includes taxes & fees
12 Nov - 13 Nov
Windsor Home with Free Parking

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 £176
includes taxes & fees
15 Nov - 16 Nov
Hampden Apartments - The Henry

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 £223
includes taxes & fees
11 Nov - 12 Nov
Heartwarming Windsor Cottage with Free Parking

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

Stylish 2 Bed Flat, 2 min walk to Windsor Castle
Windsor City Centre
The price is £277
includes taxes & fees
11 Nov - 12 Nov
Stylish 2 Bed Flat, 2 min walk to Windsor Castle

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 £200
includes taxes & fees
11 Nov - 12 Nov
Windsor Castle Amazing Cottage | 2-Min Walk | Central & Stylish

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

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 £179
includes taxes & fees
11 Nov - 12 Nov
Windsor Luxe Living – 3BR Near Windsor Castle

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 £186
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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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, apart-hotels, 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 depends 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 selected for you start as low as £128 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.

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