Windsor and Maidenhead Holidays

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Our pick of the best 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 NZ$215 per night from 5 June to 6 June
NZ$215
5 June - 6 June
includes taxes & fees
8/10 Very Good! (1,007 reviews)
This hotel is extremely big; many rooms are in flat-style blocks that feel disjointed from the main hotel, but it's good for big events. The drinks are at a high premium rate but the staff lack knowledge of how they should be served. The pool is family-friendly, so it's not good for couples looking ...

Reviewed on 4 May 2026

De Vere Beaumont Estate
Sir Christopher Wren Hotel

Sir Christopher Wren Hotel

4 out of 5
Thames Street Windsor England
The price is NZ$412 per night from 25 May to 26 May
NZ$412
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
We had a great time here. The staff was great, eating breakfast by the river was amazing! For travelers, the parking is easy if you arrange it ahead of time. The lot at the train station is a short walk. Arrange it ahead of time with the hotel. They have their own area in there for you to park. This ...

Reviewed on 4 May 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 NZ$168 per night from 28 May to 29 May
NZ$168
28 May - 29 May
includes taxes & fees
7.6/10 Good! (422 reviews)
Fantastic location right across from Windsor Castle, a great mall, tons of restaurants and an Ivy Restaurant on the corner! Staff is lovely but hotel is in need of TLC.

Reviewed on 5 May 2026

Harte and Garter
See all 534 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.