Windsor and Maidenhead Vacations & Trips from ￥330,746

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The Latest Windsor and Maidenhead Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Dao By Dorsett West London

Dao By Dorsett West London

4 out of 5
Hammersmith and Fulham
Price was ￥432,252, price is now ￥330,746 per person
￥330,746
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to London (LHR)
8.4/10 Very Good! (386 reviews)
Overall, the hotel was very nice; the staff were friendly, the rooms were clean, the breakfast was good and my young daughter was very pleased with her complimentary teddy bear. However, I booked a twin studio and the room we got was what I would class as a double; 2 single beds joined together with one duvet. The room was described as 2 single beds and if I hadn't gone with my daughter, and instead went with a friend, for example, who wasn't keen to share a duvet, this would have been a problem. The room was also described as having things that were not available; for example, dressing gowns and toothbrushes and toothpaste. When I asked reception for a toothbrush, I was informed that they didn't supply them and I needed to buy from the vending machine. Apart from those things, I was very happy with the hotel and would visit there again.

Reviewed on Apr 2, 2026

1 Hotel Mayfair

1 Hotel Mayfair

5 out of 5
London City Centre
Save 100% on your flight
Price was ￥848,736, price is now ￥551,970 per person
￥551,970
per person
Jul 5 - Jul 10
found 5 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to London (LHR)
9.6/10 Exceptional! (387 reviews)
Stunning hotel. Rooms are spacious. Staff is top notch. Bar is a blast on the weekend!

Reviewed on Apr 26, 2026

The Savoy

The Savoy

5 out of 5
London City Centre
Save 100% on your flight
Price was ￥937,356, price is now ￥628,344 per person
￥628,344
per person
Jul 5 - Jul 10
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to London (LHR)
9.6/10 Exceptional! (1,001 reviews)
Attention to detail and high levels of service made this a stay to remember! Took excellent care of me and my family all week-cannot recommend enough! If Expedia had a 10 star system, I’d give them an 11!

Reviewed on Apr 18, 2026

The Beaumont Mayfair

The Beaumont Mayfair

5 out of 5
London City Centre
Save 100% on your flight
Price was ￥922,390, price is now ￥648,048 per person
￥648,048
per person
Jul 5 - Jul 10
found 5 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to London (LHR)
9.8/10 Exceptional! (302 reviews)
Perfect location lovely staff will stay there again!!

Reviewed on Apr 20, 2026

Grand Hôtel Bellevue

Grand Hôtel Bellevue

4 out of 5
London City Centre
Price was ￥494,755, price is now ￥376,243 per person
￥376,243
per person
Jul 18 - Jul 26
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to London (LHR)
8.8/10 Excellent! (164 reviews)
The staff gave wonderful dinner recommendations. Loved how quiet it was in our room. The breakfast was worth the price as it was especially good. A lot of variety and all fresh and well made.

Reviewed on Apr 17, 2026

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 ￥30,014 per night from Apr 30 to May 1
￥30,014
￥36,017 total
Apr 30 - May 1
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
Excellent overall, Thank you.

Reviewed on Apr 27, 2026

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 ￥15,868 per night from May 4 to May 5
￥15,868
￥19,042 total
May 4 - May 5
includes taxes & fees
8/10 Very Good! (1,002 reviews)
Clean today just dated in places

Reviewed on Apr 21, 2026

De Vere Beaumont Estate
Macdonald Windsor Hotel

Macdonald Windsor Hotel

4 out of 5
23 High Street Windsor England
Fully refundableReserve now, pay when you stay
The price is ￥24,910 per night from May 21 to May 22
￥24,910
￥29,892 total
May 21 - May 22
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
The hotel is situated in the centre of Windsor very close to the castle, the staff are really helpful and knowledgeable about the local area and amenities. My wife and I were there to celebrate our wedding anniversary and we would definitely stay here again or recommend to others.

Reviewed on Apr 23, 2026

Macdonald Windsor Hotel
See all 539 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 ￥330,746. 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.