Windsor and Maidenhead Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Sasa Nikolic

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$616 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Our pick of the best Windsor and Maidenhead Hotel Deals

Sir Christopher Wren Hotel

Sir Christopher Wren Hotel

4 out of 5
Thames Street Windsor England
Fully refundableReserve now, pay when you stay
The price is NZ$260 per night from 22 Dec to 23 Dec
NZ$260
22 Dec - 23 Dec
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Staff was very helpful and accommodating. Location was very good.

Reviewed on 11 Dec 2025

Sir Christopher Wren Hotel
De Vere Beaumont Estate

De Vere Beaumont Estate

4 out of 5
Burfield Road, Berkshire Windsor England
The price is NZ$185 per night from 4 Jan to 5 Jan
NZ$185
4 Jan - 5 Jan 2026
includes taxes & fees
8/10 Very Good! (1,005 reviews)
Clearly they think about every detail - the rooms were very well thought through.

Reviewed on 13 Dec 2025

De Vere Beaumont Estate
Castle Hotel Windsor

Castle Hotel Windsor

4 out of 5
18 High Street Windsor England
Fully refundableReserve now, pay when you stay
The price is NZ$292 per night from 21 Dec to 22 Dec
NZ$292
21 Dec - 22 Dec
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
Our room was beautiful and a good size. The staff was helpful and accommodating. The location is in the center of town, steps from Windsor Castle.

Reviewed on 8 Dec 2025

Castle Hotel Windsor
See all 533 properties in Windsor and Maidenhead
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.

Frequently asked questions

How much does a Windsor and Maidenhead holiday package cost?
Be ready to book, because a trip to Windsor and Maidenhead starts from only . When you bundle your hotels, flights and car rentals into a travel package, you'll pick up the biggest bargains.
How do I get a cheap travel package to Windsor and Maidenhead?
Search for flights that suit your schedule, add a hotel to your booking and watch the savings pile up with a Windsor and Maidenhead holiday package. It's as simple as that! From hotels and flights to rental cars and activities, Expedia makes travelling on a budget easy. And with over 550 partner airlines and 1 000 000 properties throughout the world to select from, you'll never be short of choice.
How far in advance should I book my Windsor and Maidenhead holiday?
It's hard to pick the ideal time for airfares, but we usually say the earlier, the better. Plenty of international journeys on Expedia become available to compare up to 12 months in advance. If you're booking late, don't fret. Bargain prices occasionally appear just weeks before departure dates.
What does an Expedia Windsor and Maidenhead travel package include?
Flights, hotels and rental cars — we have them well covered. With Expedia, you can create your Windsor and Maidenhead travel package your way. All you have to do is work out just what you need. Once you've made your booking, you can add on extras like activities and tours. The more you bundle, the bigger the savings!
What should I know before booking a Windsor and Maidenhead travel package?
You can save big by combining your hotels, flights and rental cars. Once you've made your booking, you can add on activities or tours. Your next unforgettable holiday is only a couple of clicks away.
Can I choose my airline with a Windsor and Maidenhead Expedia holiday package?
Yes — that's the beauty of an Expedia holiday package. You're the boss! We have more than 550 partner airlines across the globe, so you have options galore when planning your Windsor and Maidenhead adventure.
If I'm not able to travel, can I cancel my Windsor and Maidenhead holiday package?
Because we understand life can throw you a few curveballs, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may charge a fee if your booking is older than that.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.