Windsor and Maidenhead Vacation Packages
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Top Windsor and Maidenhead Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Miiro Templeton Garden
London City Centre
CA $1,832
per person
Nov 1 - Nov 8
found 13 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
9.6/10 Exceptional! (732 reviews)
What a lovely hotel. The common areas and gardens are delightful, but nothing compared to the staff. Super friendly, super helpful.
Reviewed on Aug 23, 2026
Hotel Riu Plaza London The Westminster
London City Centre
CA $1,767
per person
Oct 24 - Oct 29
found 7 hours ago
Roundtrip flight included
Toronto (YTO) to London (LHR)
9/10 Wonderful! (1,966 reviews)
We stayed here before Riu took the hotel over and enjoyed the location so stayed again.
The hotel is clean and the rooms are great for an overnight stay. There are too many people for the number of lifts, and the breakfast was a bit of a three ring circus but it was clean, efficient and there was a lot of choice. Shame it’s a buffet, à la carte would be so much nicer.
Really appreciated the luggage room so we could drop our bag off before check in time.
Reviewed on Aug 23, 2026
Windsor and Maidenhead Hotel Deals
De Vere Beaumont Estate
Burfield Road, Berkshire Windsor England
Fully refundableReserve now, pay when you stay
CA $139
CA $167 total
Aug 31 - Sep 1
includes taxes & fees
8/10 Very good! (1,029 reviews)
"Horrendous service"
Reviewed on Aug 23, 2026
Sir Christopher Wren Hotel
Thames Street Windsor England
Fully refundableReserve now, pay when you stay
CA $231
CA $277 total
Aug 31 - Sep 1
includes taxes & fees
Macdonald Windsor Hotel
23 High Street Windsor England
Fully refundableReserve now, pay when you stay
CA $154
CA $185 total
Aug 30 - Aug 31
includes taxes & fees
8.8/10 Excellent! (1,017 reviews)
"Clean facilities. Daily room cleaning offered. Calm hotel friendly staff, superb location."
Reviewed on Aug 22, 2026
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 vacation package cost?
Be ready to book, because a trip to Windsor and Maidenhead starts from only CA $1,684. 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.
