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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, (215 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 NZ$508
includes taxes & fees
30 Sept - 1 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, (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 NZ$512
includes taxes & fees
1 Oct - 2 Oct
Copper Castle & Petting Farm near Legoland
A neatly made bed with a grey quilt, a tray with croissants and orange juice, and a window with a view of houses.

3. Hampden Apartments - the Diana

Hampden Apartments - the Diana
4.0 star property
Windsor City Centre
9.2 out of 10, Wonderful, (46 reviews)
"The host provided very clear instructions regarding check-in/out. The property was exactly as expected and ideal for the purpose of our trip"
United Kingdom
Craig
Hampden Apartments - the Diana
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.

4. 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 NZ$460
includes taxes & fees
25 Sept - 26 Sept
Hampden Apartments - The George
A bedroom with a large bed, two bedside tables, a tray with breakfast, and a view of the sea through the window.

5. 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
The price is NZ$490
includes taxes & fees
1 Oct - 2 Oct
Hampden Apartments - The Henry
A hot tub with a bottle of champagne and two glasses, a patio with outdoor furniture, and a house in the background.

6. Coventina

Coventina
3.0 star property
Wraysbury
The price is NZ$5,537
includes taxes & fees
27 Sept - 28 Sept
Coventina
A modern kitchen with a central island, pendant lighting, and a dining area with a glass table.

7. 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 NZ$875
includes taxes & fees
13 Oct - 14 Oct
Fabulous Central Windsor Town House
A modern house with a patio, a garden with various plants, and a wooden deck.

8. 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 NZ$603
includes taxes & fees
21 Oct - 22 Oct
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire
A bedroom with a bed, a desk, a chair, a window, and a balcony.

9. 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 NZ$323
includes taxes & fees
24 Sept - 25 Sept
Hampden Apartments - The Edward
A cozy attic bedroom with a sloped ceiling, a bed, a sofa, and a small TV.

10. Thames Retreat

Thames Retreat
3.0 star property
Wraysbury
The price is NZ$974
includes taxes & fees
27 Sept - 28 Sept
Thames Retreat
A multi-story building with a classic architectural style, featuring a symmetrical facade, large windows, and a central entrance with steps.

11. Cleveland Residences Kensington

Cleveland Residences Kensington
4.0 star property
London City Centre
8.8 out of 10, Excellent, (338 reviews)
"Loved staying at this property. Location was great, staff was wonderful especially Dimitri and it met all my expectations. I will definitely stay here again. Thank you"
United States
Davene
The price is NZ$213
includes taxes & fees
4 Oct - 5 Oct
Cleveland Residences Kensington
A hotel room with a large bed, two wall-mounted lamps, a framed artwork above the bed, and a nightstand with a cup.

12. Native Fulham Broadway

Native Fulham Broadway
3.0 star property
Hammersmith and Fulham
10.0 out of 10, Exceptional, (1 review)
"I had a fantastic stay at Native Fulham. The accommodation was excellent — spacious, comfortable, modern, and exceptionally clean. It really felt like having my own little flat in London rather than staying in a typical hotel. The location is one of the biggest advantages. Fulham Broadway station is just a short walk away, which makes getting around London incredibly convenient, and there are plenty of shops, restaurants, pubs, and supermarkets nearby. I also really appreciated having access...
United States
Peter
The price is NZ$291
includes taxes & fees
18 Oct - 19 Oct
Native Fulham Broadway
A cozy living room with a grey sofa, a wooden side table, a flat-screen TV, and a large window with curtains.

13. Mason & Fifth, Primrose Hill

Mason & Fifth, Primrose Hill
4.0 star property
Camden
9.6 out of 10, Exceptional, (238 reviews)
"Great place, good location, everything you need"
Australia
sarah
The price is NZ$466
includes taxes & fees
4 Oct - 5 Oct
Mason & Fifth, Primrose Hill
A green sofa with a mirror and a framed picture on the wall.

14. Cheval Knightsbridge

Cheval Knightsbridge
5.0 star property
London City Centre
9.6 out of 10, Exceptional, (105 reviews)
"What a great place! So convenient for a family - we traveled with our 3 kids are were so happy."
United States
Vanessa
The price is NZ$1,153
includes taxes & fees
24 Sept - 25 Sept
Cheval Knightsbridge
A courtyard with a glass door entrance, surrounded by lush greenery and a small wooden structure.

15. Vancouver Studios

Vancouver Studios
3.5 star property
London City Centre
9.0 out of 10, Wonderful, (1,138 reviews)
"Such a lovely little hotel. Well kept and friendly staff. I stayed in the Garden Room and it was very relaxing. Thank you!"
United Kingdom
Elspeth
The price is NZ$281
includes taxes & fees
27 Sept - 28 Sept
Vancouver Studios
A modern bedroom with a large bed, bedside tables, and a built-in wardrobe.

16. South Kensington Studios by DMONTRIO

South Kensington Studios by DMONTRIO
4.0 star property
London City Centre
8.8 out of 10, Excellent, (16 reviews)
"Great apartments and location was great."
United Kingdom
James
The price is NZ$367
includes taxes & fees
27 Sept - 28 Sept
South Kensington Studios by DMONTRIO
A building entrance with a set of steps leading to a door, flanked by two columns and a black iron fence.

17. Kula London Kensington

Kula London Kensington
4.0 star property
London City Centre
8.4 out of 10, Very good, (27 reviews)
"very clean and well equipped room"
United Kingdom
Marek
The price is NZ$441
includes taxes & fees
18 Oct - 19 Oct
Kula London Kensington
A hotel room with a balcony, a round table with two chairs, a vase with flowers, and a book.

18. Bob W London Holland Park

Bob W London Holland Park
2.0 star property
Kensington
7.6 out of 10, Good, (172 reviews)
"Clean and well-maintained property. The room was quite spacious and comfortable. I would definitely stay here again!"
Italy
Gianluca
The price is NZ$140
includes taxes & fees
18 Oct - 19 Oct
Bob W London Holland Park
A modern living room with a blue sofa, a wooden coffee table, and a dining area with a table and chairs.

19. Farringdon Serviced Apartments

Farringdon Serviced Apartments
4.0 star property
London City Centre
9.0 out of 10, Wonderful, (4 reviews)
"Great service great place"
United Kingdom
Samuel
The price is NZ$741
includes taxes & fees
25 Sept - 26 Sept
Farringdon Serviced Apartments
A modern bedroom with a large bed, a desk with chairs, and a TV mounted on the wall.

20. Cleveland Residences Russell Square

Cleveland Residences Russell Square
3.5 star property
London City Centre
9.2 out of 10, Wonderful, (216 reviews)
"Fantastic all around. Convenient location. Air conditioning was great too!"
United States
Lynn
The price is NZ$294
includes taxes & fees
27 Sept - 28 Sept
Cleveland Residences Russell Square
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

Holiday Inn Express Windsor by IHG

Holiday Inn Express Windsor by IHG

10/10 Excellent
"Excellent location and the staff are very friendly."
Holger 6-night trip
Posted 6 hours ago
Holiday Inn Express Windsor by IHG

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 favorite 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 NZ$460 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.