Windsor and Maidenhead Holidays

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Top Flight + Hotel Deals in Windsor and Maidenhead

Price found within the past 48 hours. Click for updated prices.
The Villa Kensington

The Villa Kensington

3.5 out of 5
London City Centre
Price was €414, price is now €269 per person
€269
per person
28 Aug - 30 Aug
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
8/10 Very good! (955 reviews)
Good value good location would come again

Reviewed on 17 May 2026

Hotel Riu Plaza London Victoria

Hotel Riu Plaza London Victoria

4 out of 5
London City Centre
Save 100% on your flight
Price was €1,165, price is now €653 per person
€653
per person
28 Aug - 1 Sept
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
9/10 Wonderful! (3,822 reviews)
Great location within walking distance to Buckingham palace, Royal Mews, Big Ben and Westminster Abbey. Great restaurants near by and a self serve market for sandwich and drinks across the street. Clean rooms, great showers and quiet.

Reviewed on 26 Jun 2026

Hotel Riu Plaza London The Westminster

Hotel Riu Plaza London The Westminster

4 out of 5
London City Centre
Save 100% on your flight
Price was €933, price is now €551 per person
€551
per person
28 Aug - 1 Sept
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
8.8/10 Excellent! (1,701 reviews)
Breakfast was good and Romero (i hope I spelled it right) was such an amazing member of staff his energy made the stay really fun

Reviewed on 26 Jun 2026

Miiro Templeton Garden

Miiro Templeton Garden

4 out of 5
London City Centre
Save 100% on your flight
Price was €467, price is now €307 per person
€307
per person
3 Aug - 5 Aug
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
9.6/10 Exceptional! (647 reviews)
This location is very nice. It’s clean, smells good, and is super close to the train. My husband and I brought our daughters age 17 and 13. We had a fully booked trip of seeing all the things… and this location was safe, clean, and nicely by public transportation. We didn’t spend a ton of time at the hotel specifically but the rooms were adorable and clean. A great size I imagine, given the price. We were really happy and I’d recommend this location.

Reviewed on 24 Jun 2026

One Hundred Shoreditch

One Hundred Shoreditch

4 out of 5
London City Centre
Save 100% on your flight
Price was €740, price is now €497 per person
€497
per person
28 Aug - 1 Sept
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
9.2/10 Wonderful! (1,635 reviews)
Second time staying there, looking forward to our third

Reviewed on 22 Jun 2026

Top hotels in Windsor and Maidenhead

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 €112 per night from 28 Jul to 29 Jul
€112
28 Jul - 29 Jul
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
"Nice and clean rooms. Staff very friendly and helpful. Beautiful grounds for the hotel and location."

Reviewed on 21 Jun 2026

De Vere Beaumont Estate
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 €208 per night from 9 Jul to 10 Jul
€208
9 Jul - 10 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"Great location to explore Windsor and/or Eaton."

Reviewed on 26 Jun 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 €108 per night from 28 Jul to 29 Jul
€108
28 Jul - 29 Jul
includes taxes & fees
7.4/10 Good! (489 reviews)
"You can’t beat the location of this hotel, but sadly that’s the only thing it has going for it. We stayed in a castle view “sleeps 4” room, and we did appreciate the pull-out sofa being set up as a bed for us upon arrival. Unfortunately we were there during the UK heat wave, and the plug-in AC unit ..."

Reviewed on 26 Jun 2026

Harte and Garter
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 holiday package cost?
Be ready to book, because a trip to Windsor and Maidenhead starts from only €269. 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.