Windsor and Maidenhead Vacations & Trips from ￥299,804

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The Latest Windsor and Maidenhead Vacation Packages

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

Hotel Riu Plaza London Victoria

4 out of 5
London City Centre
Price was ￥417,150, price is now ￥299,804 per person
￥299,804
per person
Nov 14 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to London (LHR)
8.8/10 Excellent! (2,778 reviews)
Great hotel. Great location. Breakfast was good but pancakes and waffles were dry and bland.

Reviewed on Oct 1, 2025

Treehouse Hotel London

Treehouse Hotel London

4 out of 5
London City Centre
Save 100% on your flight
Price was ￥484,889, price is now ￥332,594 per person
￥332,594
per person
Nov 11 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to London (LHR)
9/10 Wonderful! (458 reviews)
Cute boutique hotel in excellent location. Only thing I wish was that they had coffee in the lobby early on Weekends. 8 am restaurant opening was a bit late for early risers.

Reviewed on Sep 29, 2025

Hotel 41

Hotel 41

5 out of 5
London City Centre
Save 100% on your flight
Price was ￥1,748,855, price is now ￥1,240,779 per person
￥1,240,779
per person
Nov 24 - Nov 30
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to London (LHR)
10/10 Exceptional! (565 reviews)
Great customer service. Beautiful hotel. Lots of amenities

Reviewed on Sep 17, 2025

The Prince Akatoki London

The Prince Akatoki London

5 out of 5
London City Centre
Price was ￥448,198, price is now ￥327,994 per person
￥327,994
per person
Nov 11 - Nov 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to London (LHR)
9.6/10 Exceptional! (978 reviews)
Clean room, cozy vibes and very friendly staff!

Reviewed on Sep 27, 2025

1 Hotel Mayfair

1 Hotel Mayfair

5 out of 5
London City Centre
Price was ￥982,546, price is now ￥726,062 per person
￥726,062
per person
Nov 24 - Nov 30
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to London (LHR)
9.6/10 Exceptional! (296 reviews)
Staff service was out of this world. Particularly front desk and doormen personnel do an excellent job and treat you as if you are the only guest.

Reviewed on Sep 20, 2025

Windsor and Maidenhead Hotel Deals

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 ￥25,598 per night from Oct 19 to Oct 20
￥25,598
￥30,718 total
Oct 19 - Oct 20
includes taxes & fees
8.8/10 Excellent! (1,018 reviews)
"I have stayed in countless hotels over the years but The Sir Christopher Wren has to be one of the best . The location was perfect, all of the staff were friendly and helpful and the food both at breakfast and for evening meals was top quality. I can`t find a single thing I wasn`t happy with. Dave ..."

Reviewed on Sep 21, 2025

Sir Christopher Wren Hotel
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 ￥13,244 per night from Nov 2 to Nov 3
￥13,244
￥15,893 total
Nov 2 - Nov 3
includes taxes & fees
7.8/10 Good! (1,002 reviews)
"Rooms were clean and property was beautiful. Not much options to eat on property but UberEats options were helpful. Accessible property! Very beautiful inside and out."

Reviewed on Oct 1, 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 ￥18,877 per night from Oct 16 to Oct 17
￥18,877
￥22,653 total
Oct 16 - Oct 17
includes taxes & fees
9/10 Wonderful! (1,001 reviews)
"Amazing history in this hotel and right in the heart of Windsor. If you’re planning a visit to the castle this is a must stay."

Reviewed on Oct 2, 2025

Castle Hotel Windsor
See all 522 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 vacation package cost?
Be ready to book, because a trip to Windsor and Maidenhead starts from only ￥299,804. 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.