Windsor and Maidenhead Vacations & Trips from ￥265,266
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The Latest Windsor and Maidenhead Vacation Packages
- Dreamtel London Kensington
Oct 5 - Oct 11Dreamtel London Kensington + Flight
London City Centre5 nights2.5 star property6.6/10 - (946 reviews)"The photos on the website are misleading — the rooms are much smaller than they appear, and there’s barely any space to store luggage. The location, however, is excellent. There are plenty of shops nearby, and the train station is only a block away. Housekeeping serviced the room daily, which was appreciated"Reviewed July 20, 2026Roundtrip • Osaka (OSA) - London (LHR)KIX - LGW • 1 stop LHR - KIX • 1 stop￥453,614￥265,266found 4 hours agoper traveler - Hotel Shepherds Bush London
Oct 5 - Oct 11Hotel Shepherds Bush London + Flight
Hammersmith and Fulham5 nights3.5 star property8.2/10 - Very Good (593 reviews)"Good aircon in the hot weather."Reviewed July 30, 2026Roundtrip • Osaka (OSA) - London (LHR)KIX - LGW • 1 stop LHR - KIX • 1 stop￥439,496￥269,515found 4 hours agoper traveler - Miiro Templeton Garden
Oct 21 - Oct 26Miiro Templeton Garden + Flight
London City Centre5 nights4.0 star property9.6/10 - Exceptional (694 reviews)"My son and I stayed the Templeton Garden for four nights. We received small but adequate room. Unfortunately, there were many, many stains on the carpet, and an unsatisfactory amount of scuffs and dirt on the walls. In the hotel description the room was supposed to have a refrigerator. What the room really had was a box that looked like a refrigerator, but did not have a cold temperature setting. Interestingly, there were multiple items for you to purchase from the non-refrigerator box,..."Reviewed July 30, 2026Roundtrip • Tokyo (HND) - London (LHR)HND - LHR • 1 stop LHR - HND • 1 stop￥482,568￥301,466found 1 day agoper traveler - Cleveland Residences Bloomsbury
Oct 8 - Oct 12Cleveland Residences Bloomsbury + Flight
London City Centre3 nights4.0 star property9.4/10 - Exceptional (150 reviews)"Overall very clean and great location. We enjoyed our stay thoroughly. I would only ask for a daily towel change to be available. We were a couple, so having only one towel each for two summer night's was less than luxury. Everything else was perfect!"Reviewed July 29, 2026Roundtrip • Osaka (OSA) - London (LHR)KIX - LGW • 1 stop LHR - KIX • 1 stop￥434,998￥279,224found 1 day agoper traveler - Ashburn Hotel
Oct 5 - Oct 11Ashburn Hotel + Flight
London City Centre5 nights4.0 star property8.8/10 - Excellent (1,003 reviews)Roundtrip • Osaka (OSA) - London (LHR)KIX - LGW • 1 stop LHR - KIX • 1 stop￥439,124￥283,394found 4 hours agoper traveler
Windsor and Maidenhead Hotel Deals
Sir Christopher Wren Hotel
Sir Christopher Wren Hotel
Bisham Abbey National Sports Centre
Bisham Abbey National Sports Centre
Holiday Inn Express Windsor by IHG
Holiday Inn Express Windsor by IHGFrequently 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 ￥265,266. 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.