Windsor and Maidenhead Holidays
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Windsor and Maidenhead Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
St. David's Hotels
London City Centre
S$1,154
per person
4 Nov - 7 Nov
found 2 hours ago
Return direct flight included
Singapore (SIN) to London (LHR)
8.2/10 Very good! (1,477 reviews)
The location was good and the staff were friendly; the hotel was clean. However, the fact that the metro runs underneath is a major issue for light sleepers, the room was small, and the bed was too short for tall people. I highly doubt I would stay there again. Still, thank you for everything.
Reviewed on 26 Aug, 2026
Top hotels in Windsor and Maidenhead
De Vere Beaumont Estate
Burfield Road, Berkshire Windsor England
Fully refundableReserve now, pay when you stay
S$154
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (1,003 reviews)
"Negatives: Lack of air-con in the room, poor changing facilities for the swimming pool (no privacy) and the Wi-Fi stopped working on our second evening, right through to the following morning. Positives: Family room was spacious, great food/drink selection at breakfast and the swimming pool itself ..."
Reviewed on 26 Aug, 2026
Sir Christopher Wren Hotel
Thames Street Windsor England
Fully refundableReserve now, pay when you stay
S$251
31 Aug - 1 Sept
includes taxes & fees
9.2/10 Wonderful! (1,019 reviews)
"A beautiful place with nice sitting rooms and great breakfast along the Thames. Some English charm and top notch service."
Reviewed on 26 Aug, 2026
Macdonald Windsor Hotel
23 High Street Windsor England
Fully refundableReserve now, pay when you stay
S$163
20 Sept - 21 Sept
includes taxes & fees
8.8/10 Excellent! (1,021 reviews)
"Check in and out was incredibly slow. Plenty of staff around but seemingly only one capable of doing anything. Noise from the bathroom like a water tank refilling/macerater turning over every few minutes kept me awake all night. Phones have been removed from rooms under the pretext of sustainability. ..."
Reviewed on 25 Aug, 2026
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 holiday package cost?
Be ready to book, because a trip to Windsor and Maidenhead starts from only S$1,154. 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 holiday package. It's as simple as that! From hotels and flights to rental cars and activities, Expedia makes travelling 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 holiday?
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 holiday is only a couple of clicks away.
Can I choose my airline with a Windsor and Maidenhead Expedia holiday package?
Yes — that's the beauty of an Expedia holiday 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 holiday 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
