Windsor and Maidenhead Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Windsor and Maidenhead

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 4.550.479 ₫ per night from 3 Oct to 4 Oct
4.550.479 ₫
5.460.575 ₫ total
3 Oct - 4 Oct
includes taxes & fees
8.8/10 Excellent! (1,011 reviews)
"I have stayed in countless hotels over the years but The Sir Christopher Wren has to be one of the best . The location was perfect, all of the staff were friendly and helpful and the food both at breakfast and for evening meals was top quality. I can`t find a single thing I wasn`t happy with. Dave ..."

Reviewed on 21 Sept 2025

Sir Christopher Wren Hotel
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 3.355.611 ₫ per night from 16 Oct to 17 Oct
3.355.611 ₫
4.026.733 ₫ total
16 Oct - 17 Oct
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Perfectly situated in the middle of Windsor with wonderful views of the castle. The staff and property are amazingly comfortable."

Reviewed on 21 Sept 2025

Castle Hotel Windsor
De Vere Beaumont Estate

De Vere Beaumont Estate

4 out of 5
Burfield Road, Berkshire, Windsor, England
The price is 2.260.855 ₫ per night from 10 Oct to 11 Oct
2.260.855 ₫
2.713.026 ₫ total
10 Oct - 11 Oct
includes taxes & fees
7.8/10 Good! (1,009 reviews)
"we have stayed here before and returned again the surroundings are beautiful and the hotel is lovely . very clean and staff can’t do enough for you .Alex the manager was an absolute star as we had had an issue the night before he couldn’t so enough for us"

Reviewed on 19 Sept 2025

De Vere Beaumont Estate
See all 518 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 1null000null000 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.