Windsor and Maidenhead Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Our top choices for Windsor and Maidenhead holiday rentals

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 AU$412
includes taxes & fees
29 Apr - 30 Apr
Copper Castle & Petting Farm near Legoland

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
9.8 out of 10, Exceptional, (7 reviews)
"Had a great stay prior to our flight home. They had everything we needed including things for the kids (1 and 3)."
United States
Peyton T.
The price is AU$249
includes taxes & fees
13 Apr - 14 Apr
A Cosy cabin retreat - 5 mins away from Windsor and 10 mins from Legoland.

Willow Court Farm

Willow Court Farm
4.0 star property
Windsor
10.0 out of 10, Exceptional, (204 reviews)
"Studio lovely ammenities very good. "
United Kingdom
Suzy
The price is AU$435
includes taxes & fees
27 Apr - 28 Apr
Willow Court Farm

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 AU$300
includes taxes & fees
10 Apr - 11 Apr
Hampden Apartments - The Louis

Hampden Apartments - The William

Hampden Apartments - The William
3.0 star property
Eton
9.6 out of 10, Exceptional, (14 reviews)
"Always a lovely place to stay "
United Kingdom
Tony
The price is AU$254
includes taxes & fees
9 Apr - 10 Apr
Hampden Apartments - The William

Spacious, light apartment sleeps up to four

Spacious, light apartment sleeps up to four
Cookham
9.8 out of 10, Exceptional, (18 reviews)
"Beautifully refurbished property with very helpful hosts."
United Kingdom
Alexandra C.
The price is AU$401
includes taxes & fees
11 Apr - 12 Apr
Spacious, light apartment sleeps up to four

Character Victorian apartment close to Windsor town with secure parking

Character Victorian apartment close to Windsor town with secure parking
Clewer East
10.0 out of 10, Exceptional, (1 review)
"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 AU$415
includes taxes & fees
15 Apr - 16 Apr
Character Victorian apartment close to Windsor town with secure parking

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 AU$331
includes taxes & fees
15 Apr - 16 Apr
Windsor Home with Free Parking

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
Hampden Apartments - The George

2 Bed Apt| Parking| Central Windsor By Tempstay

2 Bed Apt| Parking| Central Windsor By Tempstay
Windsor City Centre
10.0 out of 10, Exceptional, (6 reviews)
"Great little apartment walkable to everything in Windsor - great space!"
Canada
Leslie C.
The price is AU$463
includes taxes & fees
27 Apr - 28 Apr
2 Bed Apt| Parking| Central Windsor By Tempstay

Relaxing guest house with Jacuzzi & boat hire

Relaxing guest house with Jacuzzi & boat hire
Wraysbury
10.0 out of 10, Exceptional, (17 reviews)
"Cabin very clean and tidy lovely location very pleasant owner would definitely recommend to others and i would definitely stay again"
United Kingdom
Wayne M.
The price is AU$486
includes taxes & fees
8 Apr - 9 Apr
Relaxing guest house with Jacuzzi & boat hire

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$496
includes taxes & fees
15 Apr - 16 Apr
Maygrove Retreat - Sleeps 2 - Jacuzzi & Boat Hire

Eton Bridge Apt- Walk Sights- Parking By Tempstay

Eton Bridge Apt- Walk Sights- Parking By Tempstay
Eton
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was comfortable and quiet. We made many day trips so it was a perfect place to return to every night. Great location for easy train adventures as well. We loved the pubs along the street and the easy access to everything we needed in Windsor, but off the busy path in quaint Eton."
United States
Maureen G.
Eton Bridge Apt- Walk Sights- Parking By Tempstay

Stay In Style With Castle Views By Tempstay

Stay In Style With Castle Views By Tempstay
Windsor City Centre
10.0 out of 10, Exceptional, (2 reviews)
"This place was perfect for us. It’s exactly as listed on the site, super cute and very comfortable plus there really is a view of the castle! We had a couple small things we needed help with and the host management company was very helpful and responsive. There’s a cut through to the long walk just up the street and you can be in the center of town in 10 min or less. Would stay again!"
United States
Amy R.
The price is AU$338
includes taxes & fees
9 Apr - 10 Apr
Stay In Style With Castle Views By Tempstay

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
The price is AU$333
includes taxes & fees
12 Apr - 13 Apr
Hampden apartments - The Richard

Modern Windsor 4 Bed Home W/ Parking - By Tempstay

Modern Windsor 4 Bed Home W/ Parking - By Tempstay
Clewer North
8.0 out of 10, Very good, (2 reviews)
"Good overall one bedroom a lot of dust on floor loft hatch came down in the night my sister hit her head also beds for 7 but only six dining chairs and lack of mirrors in rooms "
United Kingdom
Karen C.
The price is AU$675
includes taxes & fees
19 Apr - 20 Apr
Modern Windsor 4 Bed Home W/ Parking - By Tempstay

Stylish Stay- Windsor Castle- Parking- By Tempstay

Stylish Stay- Windsor Castle- Parking- By Tempstay
Windsor City Centre
8.6 out of 10, Excellent, (8 reviews)
"Great place to stay right in the middle of the town! "
United States
Shanel S.
The price is AU$515
includes taxes & fees
27 Apr - 28 Apr
Stylish Stay- Windsor Castle- Parking- By Tempstay

Windsor Castle Views & Parking - By Tempstay

Windsor Castle Views & Parking - By Tempstay
Windsor City Centre
8.0 out of 10, Very good, (1 review)
"Fabulous location. Walkable to both Windsor and Eton, as well as the railway station. We were very comfortable -- once we got the internet connection sorted. We enjoyed sitting at the table, watching the daily school parade. Hosts extremely responsive. We would book here again, when staying in UK. Thank you."
United States
Norma H.
The price is AU$580
includes taxes & fees
9 Apr - 10 Apr
Windsor Castle Views & Parking - By Tempstay

Central Apartment Facing Windsor Castle

Central Apartment Facing Windsor Castle
4.0 star property
Windsor City Centre
9.0 out of 10, Wonderful, (25 reviews)
"Amazing location, lots of shops !! "
United States
Samantha
Central Apartment Facing Windsor Castle

Cosy Chalet Close to Heathrow Airport, Windsor Castle, Legoland, Thorpe Park

Cosy Chalet Close to Heathrow Airport, Windsor Castle, Legoland, Thorpe Park
Horton
10.0 out of 10, Exceptional, (1 review)
"What a beautiful gem this place is. Absolutely wonderful.So clean and well equipped ..... cosy too.Transport excellent. Bus at end of road straight into Heathrow and the London underground.Easy walk to train station to visit London or Windsor.15 minute drive to Legoland or Thorpe Park. Will definitely stay again with the kids! "
United Kingdom
Bruce S.
The price is AU$292
includes taxes & fees
11 Apr - 12 Apr
Cosy Chalet Close to Heathrow Airport, Windsor Castle, Legoland, Thorpe Park
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.
Save an average of 15% on thousands of hotels when you're signed in

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 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$249 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.