Windsor and Maidenhead Holidays

Photo by Sasa Nikolic

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 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 Flight + Hotel Deals in Windsor and Maidenhead

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

The Drey

2 out of 5
London City Centre
Save 100% on your flight
Price was €258, price is now €140 per person
€140
per person
3 Apr - 5 Apr
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
No reviews
It’s was very clean and beautiful room close to the train station and wonderful safe area. The staff are always there ready to help and very polite. Will be staying there again

Reviewed on 4 Feb 2026

Miiro Templeton Garden

Miiro Templeton Garden

4 out of 5
London City Centre
Price was €811, price is now €449 per person
€449
per person
24 Apr - 26 Apr
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
9.6/10 Exceptional! (270 reviews)
clean place, polite and helpful staff etc.

Reviewed on 6 Feb 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 €623, price is now €351 per person
€351
per person
3 Apr - 5 Apr
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
8.8/10 Excellent! (3,010 reviews)
Staff was very friendly, room was clean and we had a great stay.

Reviewed on 7 Feb 2026

Ember Locke Kensington

Ember Locke Kensington

4 out of 5
London City Centre
Save 100% on your flight
Price was €387, price is now €225 per person
€225
per person
20 Mar - 22 Mar
found 20 hours ago
Return flight included
Cork (ORK) to London (LHR)
9.2/10 Wonderful! (1,044 reviews)
Staff were great. However, our room smelt like it had been smoked in. Air conditioning was stuck on heat so had to sleep with the window open by busy high street.

Reviewed on 5 Feb 2026

Park Grand Paddington Court

Park Grand Paddington Court

4 out of 5
London City Centre
Save 100% on your flight
Price was €387, price is now €231 per person
€231
per person
20 Mar - 22 Mar
found 20 hours ago
Return flight included
Cork (ORK) to London (LHR)
7.6/10 Good! (1,962 reviews)
Lovely, clean, comfortable room in an ideal location for our stay. Lovely, welcoming staff and excellent customer service. The breakfast was nice too, and regularly replaced items made it hot and fresh. Would recommend staying here again.

Reviewed on 24 Jan 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 €123 per night from 15 Feb to 16 Feb
€123
15 Feb - 16 Feb
includes taxes & fees
8/10 Very Good! (1,003 reviews)
Amazing hotel and location. Staff were incredibly friendly and helpful. The pool and gym are excellent! Only downside to the bar is the don’t have Guinness on draft

Reviewed on 6 Feb 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 €173 per night from 1 Mar to 2 Mar
€173
1 Mar - 2 Mar
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
A beautiful hotel, fantastic location with great facilities and staff. Will definitely go there again.

Reviewed on 8 Feb 2026

Sir Christopher Wren Hotel
Harte and Garter

Harte and Garter

2 out of 5
31 High St Windsor England
Fully refundableReserve now, pay when you stay
The price is €73 per night from 1 Mar to 2 Mar
€73
1 Mar - 2 Mar
includes taxes & fees
7.6/10 Good! (353 reviews)
Excellent location and reasonably priced.

Reviewed on 4 Feb 2026

Harte and Garter
See all 524 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 €140. 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.