Windsor and Maidenhead Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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 Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza London The Westminster

Hotel Riu Plaza London The Westminster

4 out of 5
London City Centre
Price was CA $2,584, price is now CA $1,827 per person
CA $1,827
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
8.8/10 Excellent! (1,563 reviews)
Staff was helpful. The rooms were nice and clean. Great location. Would recommend

Reviewed on May 23, 2026

Corinthia London

Corinthia London

5 out of 5
London City Centre
Price was CA $6,756, price is now CA $4,457 per person
CA $4,457
per person
Aug 15 - Aug 21
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
9.8/10 Exceptional! (1,006 reviews)
Awesome property, great staff and roomy comfortable accommodations. Breakfast is awesome. On-site restaurant (Kerriges) is superb. Quiet location close to shopping, shows and the Underground. Bring a device that can Cast your content to TV so you don't have to try to find something to watch on the confusing TV/Media System, the channel guide is awful. The WiFi is lightning fast and great for streaming.

Reviewed on Apr 30, 2026

Hotel Riu Plaza London Victoria

Hotel Riu Plaza London Victoria

4 out of 5
London City Centre
Price was CA $2,714, price is now CA $1,892 per person
CA $1,892
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
9/10 Wonderful! (3,663 reviews)
The location is unbeatable. The breakfast buffet is unbelievably good. The room was big and comfortable. This is probably the best hotel we’ve stayed for the past few years.

Reviewed on May 22, 2026

Hammersmith Mews by Viridian Apartments

Hammersmith Mews by Viridian Apartments

3 out of 5
Hammersmith
Price was CA $6,049, price is now CA $4,250 per person
CA $4,250
per person
Jul 24 - Aug 3
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to London (LHR)
9/10 Wonderful! (2 reviews)
The check in process was not very smooth but other than that great apartment and location.

Reviewed on Apr 1, 2026

Dao by Dorsett North London

Dao by Dorsett North London

4 out of 5
Haringey
Price was CA $3,890, price is now CA $2,737 per person
CA $2,737
per person
Jun 29 - Jul 7
found 1 day ago
Roundtrip flight included
Montreal (YUL) to London (LHR)
9.6/10 Exceptional! (14 reviews)
Staff at the hotel were exceptionally helpful. The room was very clean and well equipped for self catering- although we did not need this. Location is great for Crouch End and also convenient to access central London.

Reviewed on May 1, 2026

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 CA $180 per night from May 31 to Jun 1
CA $180
CA $216 total
May 31 - Jun 1
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"Great"

Reviewed on May 23, 2026

De Vere Beaumont Estate
Sir Christopher Wren Hotel

Sir Christopher Wren Hotel

4 out of 5
Thames Street Windsor England
The price is CA $278 per night from May 25 to May 26
CA $278
CA $334 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"All went very well, good room and breackfast. Helpful staff"

Reviewed on May 22, 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 CA $127 per night from May 31 to Jun 1
CA $127
CA $152 total
May 31 - Jun 1
includes taxes & fees
Harte and Garter
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.
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All Inclusive Vacations
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Frequently asked questions

How much does a Windsor and Maidenhead vacation package cost?
Be ready to book, because a trip to Windsor and Maidenhead starts from only CA $1,827. 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 vacation package. It's as simple as that! From hotels and flights to rental cars and activities, Expedia makes traveling 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 vacation?
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 vacation is only a couple of clicks away.
Can I choose my airline with a Windsor and Maidenhead Expedia vacation package?
Yes — that's the beauty of an Expedia vacation 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 vacation 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.