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.
Hybrid Resi Greenwich

Hybrid Resi Greenwich

3.5 out of 5
Greenwich
per person
Oct 20 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to London (LHR)
8.6/10 Excellent! (4 reviews)
Spacious Serviced Apartments Canary Wharf

Spacious Serviced Apartments Canary Wharf

4 out of 5
Canary Wharf
per person
Oct 20 - Oct 28
found 5 hours ago
Roundtrip flight included
Toronto (YYZ) to London (LHR)
7.6/10 Good! (14 reviews)
The Savoy

The Savoy

5 out of 5
London City Centre
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
9.6/10 Exceptional! (1,001 reviews)
The property itself is nice but the rooms are not; the junior suite I stayed in was dingy with no view which made it feel dark, dreary and dilapidated.

Reviewed on Jul. 31, 2025

Ellen Kensington

Ellen Kensington

4 out of 5
London City Centre
per person
Oct 5 - Oct 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
8.4/10 Very Good! (36 reviews)
Great room, even though the price was a bit high. I asked for a handicap, friendly room. Even though there was an elevator to the third floor, there are still steps involved, which was not easy.

Reviewed on Jul. 23, 2025

Collingham Road - 2 Bedroom Apartment I

Collingham Road - 2 Bedroom Apartment I

2 out of 5
London City Centre
per person
Sep 4 - Sep 14
found 5 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to London (LHR)
No reviews

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 $163 per night from Aug 6 to Aug 7
CA $163
CA $196 total
Aug 6 - Aug 7
includes taxes & fees
7.8/10 Good! (1,002 reviews)
Superb hotel - Need to invest in 'in-room' comfort
"This hotel is simply beautiful. The grounds are superb, and the overall amenties and facilties are great. However, I just don't get why any hotel in this day and age doesn't offer air-conditioning in the rooms. I mean, it's standard in a Premier Inn these days. As it happens, a previous resident ..."

Reviewed on Jul. 25, 2025

De Vere Beaumont Estate
Castle Hotel Windsor

Castle Hotel Windsor

4 out of 5
18 High Street, Windsor, England
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from Aug 17 to Aug 18
CA $220
CA $264 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Very nice, excellent staff."

Reviewed on Jul. 31, 2025

Castle Hotel Windsor
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 CA $236 per night from Aug 10 to Aug 11
CA $236
CA $284 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (1,013 reviews)
A pleasant place to stay
"Just a very pleasant place to stay and good value for money"

Reviewed on Jul. 29, 2025

Sir Christopher Wren Hotel
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.
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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 $1,579. 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.