Windsor and Maidenhead Holidays from AU$6,579

Book a Hotel + Flight or Car together to unlock savings

Photo by Sasa Nikolic

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Windsor and Maidenhead Holiday Deals

Price found within the past 48 hours. Click for updated prices.
San Domenico House

San Domenico House

5 out of 5
London City Centre
Price was AU$8,192, price is now AU$6,579 per person
AU$6,579
per person
12 June - 21 June
found 1 day ago
Return direct flight included
Singapore (SIN) to London (LHR)
9.4/10 Exceptional! (385 reviews)
Home away from home, very charming and warm welcoming reception. Rooms are very clean and rustic. I highly recommend this hotel

Reviewed on 6 Mar 2026

The Savoy

The Savoy

5 out of 5
London City Centre
Price was AU$13,993, price is now AU$10,172 per person
AU$10,172
per person
12 June - 21 June
found 1 day ago
Return direct flight included
Singapore (SIN) to London (LHR)
9.6/10 Exceptional! (1,002 reviews)
Great staff. Loved the American Bar. Great drinks and nibbles

Reviewed on 27 Mar 2026

The Beaumont Mayfair

The Beaumont Mayfair

5 out of 5
London City Centre
Price was AU$14,237, price is now AU$10,665 per person
AU$10,665
per person
12 June - 21 June
found 1 day ago
Return direct flight included
Singapore (SIN) to London (LHR)
9.8/10 Exceptional! (292 reviews)
I always receive a warm welcome at the Beaumont - only here for one night, but such a convenient jumping off point for west end. See you next time!

Reviewed on 28 Mar 2026

The Capital Hotel, Apartments & Townhouse - Small Luxury Hotels of The World

The Capital Hotel, Apartments & Townhouse - Small Luxury Hotels of The World

5 out of 5
London City Centre
Price was AU$8,889, price is now AU$7,082 per person
AU$7,082
per person
12 June - 21 June
found 1 day ago
Return direct flight included
Singapore (SIN) to London (LHR)
9.2/10 Wonderful! (674 reviews)
Our stay at the Capital hotel was wonderful. Traveled with a 3yo toddler and my mom, which were their first time in London. Our room was the 1 bedroom. It was spacious and incredibly clean. The kitchen was well stocked and there’s even a washer and dryer. The location was fantastic as it was only a few steps from Harrods’ and the area was well located to get to all the attractions with the buses. Walking distance to the National and Science museums. We stayed for 4 nights and were very comfortable. Best of all were the staff. They were very accommodating especially with a toddler and assisted with every request. My daughter wanted olives at breakfast and they made her so happy with olives each morning. Or magically appeared with crayons and coloring books when she only mentioned it to me mere seconds before if she could color but I didn’t have any with us. The staff were really exceptional. Thank you for making our trip so special.

Reviewed on 30 Mar 2026

The Dorchester

The Dorchester

5 out of 5
London City Centre
Price was AU$15,764, price is now AU$12,682 per person
AU$12,682
per person
12 June - 21 June
found 1 day ago
Return direct flight included
Singapore (SIN) to London (LHR)
9.6/10 Exceptional! (406 reviews)
Great room and extremely helpful and friendly staff. The number and quality of eating and drinking options on the premises really sets Dorchester apart. Glad I spent my last night in town on this trip, and will plan to return for more extended stays in the future.

Reviewed on 5 Feb 2026

Windsor and Maidenhead Essential Information

Language
English
Currency
British pounds sterling
Closest Airport
Heathrow Airport (LHR)

Our pick of the best 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 AU$266 per night from 12 Apr to 13 Apr
AU$266
12 Apr - 13 Apr
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
Great hotel. Great location. Great breakfast. Wonderful staff too

Reviewed on 6 Apr 2026

Sir Christopher Wren Hotel
Harte and Garter

Harte and Garter

3 out of 5
31 High St Windsor England
Fully refundableReserve now, pay when you stay
The price is AU$152 per night from 21 Apr to 22 Apr
AU$152
21 Apr - 22 Apr
includes taxes & fees
7.6/10 Good! (399 reviews)
First impressions at reception and check in were excellent. Room was big and very clean. French doors had gaps and let in cold and noise and boy was it noisy from 3pm to 2am it was non stop, motorbikes, car horns and people shouting and screaming. 6am started again with lorries and dustbins being ...

Reviewed on 6 Apr 2026

Harte and Garter
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 AU$189 per night from 17 Apr to 18 Apr
AU$189
17 Apr - 18 Apr
includes taxes & fees
8/10 Very Good! (1,005 reviews)
Beautiful estate.

Reviewed on 6 Apr 2026

De Vere Beaumont Estate
See all 536 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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 AU$6,579. 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.