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Windsor and Maidenhead Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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

Top Windsor and Maidenhead flight + hotel deals

Price found within the past 48 hours. Click for updated prices.
  • 3 Jan - 5 Jan

    London Lodge Hotel + Flight

    London City Centre
    2 nights
    3.0 star property
    8.6/10 - Excellent (1,000 reviews)
    Return • Cork (ORK) - London (LHR)
    ORK - STN • Direct STN - ORK • Direct
    €424
    €216
    per traveller
    found 1 day ago
    London Lodge Hotel
  • 11 Dec - 13 Dec

    Residence Inn by Marriott London Kensington + Flight

    London City Centre
    2 nights
    4.0 star property
    8.6/10 - Excellent (1,385 reviews)
    "A little out of the way in Kensington but very walkable. Has everything you need and tesco close by. I got a great price so can't complain and will book again."
    Reviewed November 9, 2026
    Return • Dublin (DUB) - London (LHR)
    DUB - STN • Direct STN - DUB • Direct
    €689
    €342
    per traveller
    found 20 hours ago
    Residence Inn by Marriott London Kensington
  • 2 Feb - 6 Feb

    Residence Inn by Marriott London Tower Bridge + Flight

    London City Centre
    4 nights
    4.0 star property
    8.4/10 - Very good (1,000 reviews)
    "Enjoyed our stay. Some staff just ok"
    Reviewed November 8, 2026
    Return • Dublin (DUB) - London (LHR)
    DUB - LHR • Direct LHR - DUB • Direct
    €804
    €449
    per traveller
    found 2 days ago
    Residence Inn by Marriott London Tower Bridge
  • 2 Feb - 6 Feb

    Garden Court Hotel + Flight

    London City Centre
    4 nights
    3.0 star property
    8.0/10 - Very good (1,004 reviews)
    "Room was a bit different from the pictures when we booked it especially the bathroom. I'd say the room was clean and good for a short stay but you're not getting the room you booked. The bathroom looked like a plastic bathroom you'd find in campervans, there was mold and a very specific smell that I can't describe. This is not what the pictures advertised. The area was amazing though, so many shops, food places etc. I'd recommend just for the area."
    Reviewed November 8, 2026
    Return • Dublin (DUB) - London (LHR)
    DUB - LHR • Direct LHR - DUB • Direct
    €493
    €285
    per traveller
    found 2 days ago
    Garden Court Hotel
  • 11 Dec - 13 Dec

    Dorsett Canary Wharf London + Flight

    Canary Wharf
    2 nights
    4.0 star property
    8.8/10 - Excellent (308 reviews)
    "Great hotel, room was clean and they let us check in slightly early! Perfect for a couple nights stay in London. Will definitely be back if staying in Canary Wharf again"
    Reviewed November 9, 2026
    Return • Dublin (DUB) - London (LHR)
    DUB - STN • Direct STN - DUB • Direct
    Save 100% on your flight
    €466
    €279
    per traveller
    found 20 hours ago
    Dorsett Canary Wharf London

Windsor and Maidenhead Hotel Deals

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 €216. 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.