Windsor and Maidenhead Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • Better together

    Save up to ₩234,741 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

Windsor and Maidenhead Hotel Deals

De Vere Beaumont Estate

De Vere Beaumont Estate

4 out of 5
Burfield Road, Berkshire, Windsor, England
Fully refundableReserve now, pay when you stay
The price is ₩135,736 per night from Nov 9 to Nov 10
₩135,736
₩162,883 total
Nov 9 - Nov 10
includes taxes & fees
7.8/10 Good! (1,018 reviews)
Breakfast was OK. Would not say it was great. Also it was supposed to run until 10am. We arrived at 9:30 to grab a quick bite and before we even sat down all the breakfast things were being cleared away. Not very welcoming.

Reviewed on Oct 17, 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 ₩182,501 per night from Oct 26 to Oct 27
₩182,501
₩219,001 total
Oct 26 - Oct 27
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
Quaint hotel with 5-Star service and atmosphere. Efficient layout that was workable in the available space, didn't feel cramped. Only down side was the time to draw hot water, especially at the sink, but even in the shower. However, once it got hot, it was very hot. Complimentary breakfast buffet ...

Reviewed on Oct 17, 2025

Castle Hotel Windsor
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 ₩247,486 per night from Oct 30 to Oct 31
₩247,486
₩296,983 total
Oct 30 - Oct 31
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
Great location

Reviewed on Oct 18, 2025

Sir Christopher Wren Hotel
See all 522 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 vacation 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 vacation package. It's as simple as that! From hotels and flights to rental cars and activities, Expedia makes traveling 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 vacation?
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 vacation is only a couple of clicks away.
Can I choose my airline with a Windsor and Maidenhead Expedia vacation package?
Yes — that's the beauty of an Expedia vacation 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 vacation 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.