Windsor and Maidenhead Holidays

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    Save up to S$134 when you book a flight and hotel together*

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Windsor and Maidenhead Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Staines Riverside by Charles Hope

Staines Riverside by Charles Hope

4 out of 5
Price was S$2,249, price is now S$1,559 per person
S$1,559
per person
6 Feb - 14 Feb
found 16 hours ago
Return direct flight included
Kuala Lumpur (KUL) to London (LHR)
15.2/10 Exceptional! (13 reviews)
Lovely apartment, only downfalls was the floor was dirty and hadn’t been cleaned, one of the beds sheets had staines of some sort. Beds were uncomfortable and the parking opposite only allows you to book until 12 midnight, you then have to wake up at 6am to pay again as there’s no option to pay for 24hrs obviously this has nothing to do with the owners but something to be aware when booking.

Reviewed on 1 Dec, 2024

Park Lane Apartments Crawford Place

Park Lane Apartments Crawford Place

4 out of 5
London City Centre
Save 100% on your flight
Price was S$4,282, price is now S$2,412 per person
S$2,412
per person
6 Feb - 14 Feb
found 16 hours ago
Return direct flight included
Kuala Lumpur (KUL) to London (LHR)
16/10 Exceptional! (17 reviews)
Clean room full kitchen nonworking washing machine

Reviewed on 24 Sept, 2025

Park Lane Apartments - Shaw House

Park Lane Apartments - Shaw House

3.5 out of 5
London City Centre
Save 100% on your flight
Price was S$4,033, price is now S$2,306 per person
S$2,306
per person
6 Feb - 14 Feb
found 16 hours ago
Return direct flight included
Kuala Lumpur (KUL) to London (LHR)
16/10 Exceptional! (8 reviews)
Lots of room, safe, and close enough to walk to Hyde park, Buckingham palace, West End and other attractions.

Reviewed on 3 Apr, 2024

The Franklin London - Starhotels Collezione

The Franklin London - Starhotels Collezione

5 out of 5
London City Centre
Save 100% on your flight
Price was S$4,217, price is now S$2,470 per person
S$2,470
per person
6 Feb - 14 Feb
found 16 hours ago
Return direct flight included
Kuala Lumpur (KUL) to London (LHR)
18.4/10 Exceptional! (513 reviews)
Great staff, great location

Reviewed on 19 Oct, 2025

Macdonald Windsor Hotel

Macdonald Windsor Hotel

4 out of 5
Windsor City Centre
Price was S$2,695, price is now S$1,963 per person
S$1,963
per person
7 Feb - 19 Feb
found 5 hours ago
Return direct flight included
Kuala Lumpur (KUL) to London (LHR)
17.6/10 Exceptional! (1,000 reviews)
Professional comfortable clean

Reviewed on 18 Nov, 2025

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Top hotels in Windsor and Maidenhead

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$151 per night from 30 Nov to 1 Dec
S$151
30 Nov - 1 Dec
includes taxes & fees
7.8/10 Good! (1,011 reviews)
Lovely hotel

Reviewed on 22 Nov, 2025

De Vere Beaumont Estate
Castle Hotel Windsor

Castle Hotel Windsor

4 out of 5
18 High Street Windsor England
The price is S$176 per night from 14 Dec to 15 Dec
S$176
14 Dec - 15 Dec
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
We throughly enjoyed our stay at Castle Hotel! The room was clean and cozy, bed and pillows were very comfortable and the staff was so kind and accommodating. This hotel is in a wonderful location, close to many shops/ pubs and right across the road from Windsor Castle. Highly recommend this ...

Reviewed on 18 Nov, 2025

Castle Hotel Windsor
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$204 per night from 14 Dec to 15 Dec
S$204
14 Dec - 15 Dec
includes taxes & fees
8.8/10 Excellent! (1,008 reviews)
Clean lovely room but many many stairs. Staff were great and helped me with baggage. No handrail on the left tho -(right arm in sling). Great breakfast and dinner with pot pie was fantastic.

Reviewed on 19 Nov, 2025

Sir Christopher Wren Hotel
See all 520 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 holiday package cost?
Be ready to book, because a trip to Windsor and Maidenhead starts from only S$1,559. 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.