Windsor and Maidenhead Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Windsor and Maidenhead Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cleveland Residences Russell Square

Cleveland Residences Russell Square

3.5 out of 5
London City Centre
Price was CA $2,409, price is now CA $1,710 per person
CA $1,710
per person
Sep 9 - Sep 14
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to London (LHR)
9.2/10 Wonderful! (178 reviews)

Dreamtel London Kensington

Dreamtel London Kensington

2.5 out of 5
London City Centre
Price was CA $2,760, price is now CA $1,805 per person
CA $1,805
per person
Sep 26 - Oct 6
found 13 hours ago
Roundtrip flight included
Montreal (YMQ) to London (LHR)
6.6/10 (942 reviews)
Very good location, clean room

Reviewed on Jul 2, 2026

Apartment in Folkestone Near Sandgate Beach

Apartment in Folkestone Near Sandgate Beach

5 out of 5
Price was CA $8,919, price is now CA $6,240 per person
CA $6,240
per person
Sep 28 - Oct 3
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to London (LHR)
No reviews

Cleveland Residences Bloomsbury

Cleveland Residences Bloomsbury

4 out of 5
London City Centre
Price was CA $2,612, price is now CA $1,840 per person
CA $1,840
per person
Sep 9 - Sep 14
found 7 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to London (LHR)
9.6/10 Exceptional! (144 reviews)
This place is beautiful. They put a lot of thought into all the details. A true boutique feel. I would absolutely stay again. It is walking distance to King’s Cross Station and the surrounding area is delightful. The only reason I docked it a star is due to the check in process. I booked the place about 48 hours before arrival. They reached out through Expedia asking the time I expected to arrive and they advised I needed to fill a form out. I replied with my arrival time and I advised them the form wouldn’t open correctly (I am a tech capable individual). I did not hear back prior to the day of check in. I understand I had a short booking turn around time, but it shouldn’t have been an option if it would be too much to accommodate. I arrived on check in day a bit early with my luggage just wanting to ask if they could hold it until my room was ready. They did agree to do so, but they looked incredibly put out and acted as if I was really bothering them. I had replied asap on Expedia and had done everything they asked me to that I could. The service could have been friendlier over all. I also don’t perceive this was a cultural difference thing.

Reviewed on Jun 28, 2026

The Savoy

The Savoy

5 out of 5
London City Centre
Price was CA $6,720, price is now CA $4,821 per person
CA $4,821
per person
Sep 30 - Oct 6
found 11 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to London (LHR)
9.8/10 Exceptional! (1,002 reviews)
The best In london. Amazing place and nothing is too much for them. I got my Paddington tickets through the Guest Relations desk - no one else could have done that!

Reviewed on Jul 6, 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 $155 per night from Jul 12 to Jul 13
CA $155
CA $186 total
Jul 12 - Jul 13
includes taxes & fees
8.2/10 Very good! (1,002 reviews)
"Loved to beautiful property and fantastic breakfast. Only downside is no air conditioning and pool access is limited to early closing so we could never get to pool after day out as a family."

Reviewed on Jul 7, 2026

De Vere Beaumont Estate
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 $147 per night from Jul 13 to Jul 14
CA $147
CA $176 total
Jul 13 - Jul 14
includes taxes & fees
7.4/10 Good! (506 reviews)
"The hotel and room were not as advertised. The a/c was only in a few rooms and with some minor touch ups the rooms could be described as quaint. Instead they were just disappointing and sad."

Reviewed on Jul 6, 2026

Harte and Garter
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 $265 per night from Aug 2 to Aug 3
CA $265
CA $318 total
Aug 2 - Aug 3
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"The Sir Christopher Wren Hotel is a brilliant collection of historic properties located on the Thames River and an easy walk to Windsor Castle and shopping. Helpful staff at check-in and check-out and in the Brasserie restaurant with a tasty pub/bistro menu. Room was spacious with a bathtub (and ..."

Reviewed on Jul 8, 2026

Sir Christopher Wren Hotel
See all 521 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 $1,710. 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.