Windsor and Maidenhead Holiday Rentals

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Our top choices for Windsor and Maidenhead holiday rentals

Riverwalk Apartment One

Riverwalk Apartment One
3.5 star property
Slough
10.0 out of 10, Exceptional, (3 reviews)
"Really great stay and convenient for both Windsor and London. "
United Kingdom
David
The price is NZ$906
includes taxes & fees
12 May - 13 May
Riverwalk Apartment One

Willow Court Farm

Willow Court Farm
4.0 star property
Windsor
10.0 out of 10, Exceptional, (204 reviews)
"We enjoyed our very short stay and would like to return for longer next time. The lodge had everything we needed and our children loved the bunk beds. We all enjoyed feeding the animals in the morning the next day. "
United Kingdom
Louise
The price is NZ$492
includes taxes & fees
19 May - 20 May
Willow Court Farm

Copper Castle & Petting Farm near Legoland

Copper Castle & Petting Farm near Legoland
4.0 star property
Windsor
10.0 out of 10, Exceptional, (1 review)
"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 NZ$375
includes taxes & fees
10 May - 11 May
Copper Castle & Petting Farm near Legoland

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
The price is NZ$339
includes taxes & fees
8 May - 9 May
Hampden Apartments - The Louis

Coventina

Coventina
3.0 star property
Wraysbury
The price is NZ$5,472
includes taxes & fees
18 May - 19 May
Coventina

Hampden Apartments - The Henry

Hampden Apartments - The Henry
4.0 star property
Windsor City Centre
9.0 out of 10, Wonderful, (20 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

Stunning Central Windsor Town House

Stunning Central Windsor Town House
3.0 star property
Windsor City Centre
10.0 out of 10, Exceptional, (3 reviews)
"The house was perfect! The standard of the accommodation was excellent and it was located close to restaurants and all local attractions."
United Kingdom
Lisa
Stunning Central Windsor Town House

Hampden Apartments - The George

Hampden Apartments - The George
4.0 star property
Windsor City Centre
9.2 out of 10, Wonderful, (35 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$420
includes taxes & fees
6 May - 7 May
Hampden Apartments - The George

Hampden apartments - The Richard

Hampden apartments - The Richard
4.0 star property
Windsor City Centre
8.8 out of 10, Excellent, (10 reviews)
"We had a fabulous overnight stay, the location was perfect and I would highly recommend staying here - Thank you!"
United States
Pamela
Hampden apartments - The Richard

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$596
includes taxes & fees
17 May - 18 May
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

Hampden Apartments - The Anne

Hampden Apartments - The Anne
3.5 star property
Windsor City Centre
8.6 out of 10, Excellent, (7 reviews)
"Really nice apartment close to the centre of Windsor. Handy parking space close by that will save you some money as the local Q park is about £45 for 48 hours! "
United Kingdom
Anonymous traveller
Hampden Apartments - The Anne

The Annex

The Annex
2.0 star property
Slough
The price is NZ$1,210
includes taxes & fees
16 May - 17 May
The Annex

Hampden Apartments - The Catherine

Hampden Apartments - The Catherine
4.0 star property
Windsor City Centre
10.0 out of 10, Exceptional, (5 reviews)
"Brilliant stay, excellent location."
United Kingdom
Sophie
Hampden Apartments - The Catherine

Thames Retreat

Thames Retreat
3.0 star property
Wraysbury
The price is NZ$963
includes taxes & fees
18 May - 19 May
Thames Retreat

The Boathouse London

The Boathouse London
4.0 star property
London City Centre
9.2 out of 10, Wonderful, (20 reviews)
"Really unique experience to stay on a canal boat that is extremely well furnished and close to some great dining options (and Heathrow Express from Paddington station)."
United States
Adam
The price is NZ$517
includes taxes & fees
12 May - 13 May
The Boathouse London

Bob W London Holland Park

Bob W London Holland Park
2.0 star property
Kensington
8.2 out of 10, Very good, (99 reviews)
"Nice clean room and bathroom although the bathroom was so small I had to contort myself to get into the shower. Breakfast at a nearby cafe was excellent. Overall very happy and would stay there again."
Australia
Sarah
The price is NZ$127
includes taxes & fees
25 May - 26 May
Bob W London Holland Park

Mason & Fifth, Primrose Hill

Mason & Fifth, Primrose Hill
4.0 star property
Camden
9.6 out of 10, Exceptional, (219 reviews)
"Always a good stay "
United States
Marsha
The price is NZ$528
includes taxes & fees
11 May - 12 May
Mason & Fifth, Primrose Hill

Cleveland Residences Kensington

Cleveland Residences Kensington
4.0 star property
London City Centre
8.8 out of 10, Excellent, (244 reviews)
"Great place to stay"
United Kingdom
STUART
The price is NZ$258
includes taxes & fees
31 May - 1 June
Cleveland Residences Kensington

The Apartments by The Sloane Club

The Apartments by The Sloane Club
4.0 star property
London City Centre
9.6 out of 10, Exceptional, (86 reviews)
"If you want to experience a quintessential, slightly posh British apartment lifestyle, I highly recommend this place. The interior is comfortable and kept spotlessly clean. For long-term business travelers like myself, it is well-equipped with everything you need, including a kitchen, fridge, and washing machine. The location is also perfect, allowing for a truly relaxing stay. I would definitely love to stay here again."
Japan
SEIKO
The price is NZ$794
includes taxes & fees
29 May - 30 May
The Apartments by The Sloane Club

47 Park Street - Grand Residences by Marriott

47 Park Street - Grand Residences by Marriott
4.0 star property
London City Centre
9.8 out of 10, Exceptional, (124 reviews)
"We loved the property. It was clean, very elegant. "
United States
Sandra
The price is NZ$1,553
includes taxes & fees
12 May - 13 May
47 Park Street - Grand Residences by Marriott
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

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$296 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.