Windsor and Maidenhead Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

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

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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 ₩199,107 per night from Jun 5 to Jun 6
₩199,107
₩238,928 total
Jun 5 - Jun 6
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"Lovely hotel by Legoland Windsor, perfect getaway to Legoland or Windsor castle. Amazing breakfast options, clean property, and spacious play area for children. The only downside is the number of charging ports (only 4 spaces by the reception) and two were occupied by a rental EV but not charging ..."

Reviewed on May 17, 2026

De Vere Beaumont Estate
Sir Christopher Wren Hotel

Sir Christopher Wren Hotel

4 out of 5
Thames Street Windsor England
The price is ₩286,079 per night from May 31 to Jun 1
₩286,079
₩343,295 total
May 31 - Jun 1
includes taxes & fees
9/10 Wonderful! (1,003 reviews)
"All went very well, good room and breackfast. Helpful staff"

Reviewed on May 22, 2026

Sir Christopher Wren Hotel
Harte and Garter

Harte and Garter

3 out of 5
31 High St Windsor England
Fully refundableReserve now, pay when you stay
The price is ₩150,308 per night from Jun 7 to Jun 8
₩150,308
₩180,361 total
Jun 7 - Jun 8
includes taxes & fees
7.6/10 Good! (440 reviews)
"Hotel position was great but room was dated And in poor repair but bed was good"

Reviewed on May 21, 2026

Harte and Garter
See all 515 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.