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.
Dreamtel London Kensington
Hotel Riu Plaza London Victoria
Wilde Aparthotels London Liverpool St.
St. James' Court, A Taj Hotel, London
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Top hotels in Windsor and Maidenhead

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 S$231 per night from 16 Dec to 17 Dec
S$231
includes taxes & fees
16 Dec - 17 Dec
8.6/10 Excellent! (1,001 reviews)
"We absolutely loved the hotel the staff the food the service was amazing"

Reviewed on 17 Nov,2024

Sir Christopher Wren Hotel
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 S$199 per night from 22 Dec to 23 Dec
S$199
includes taxes & fees
22 Dec - 23 Dec
9/10 Wonderful! (1,000 reviews)
"Alot of noise from a generator. It is an older building and we coukd hear everthing from the room above"

Reviewed on 8 Nov,2024

Castle Hotel Windsor
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 S$159 per night from 19 Dec to 20 Dec
S$159
includes taxes & fees
19 Dec - 20 Dec
7.4/10 Good! (989 reviews)
Amazing hotel
"Yet again an amazing hotel, been to most of of the De vere hotels! Room amazing, albeit quite a trek from reception ! 1705 restaurant was a bit of a let down, as I asked for a plain chicken filet burger but it came with a pickle relish inside and the chips were still hard inside, did advise staff ..."

Reviewed on 19 Nov,2024

De Vere Beaumont Estate
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$1,179. 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.