Windsor and Maidenhead Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

  • Better together

    Save up to £750 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

    Packages with flights are ATOL protected

Top Windsor and Maidenhead Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Dreamtel London Kensington

Dreamtel London Kensington

2.5 out of 5
London City Centre
Save 100% on your flight
Price was £417, price is now £240 per person
£240
per person
28 Aug - 30 Aug
found 12 hours ago
Return flight included
Aberdeen (ABZ) to London (LHR)
6.6/10 (939 reviews)
Room seemed clean but was in need of repair. Floor was coming up. Air conditioning didn't work and tiles grouting was discoloured. Bed was comfortable and clean. The hotel was closed to shops etc, lots of vans and trucks arrived during the night, making it noisy as we had to have windows open as air conditioning didn't work.

Reviewed on 19 Apr 2026

Hotel Riu Plaza London The Westminster

Hotel Riu Plaza London The Westminster

4 out of 5
London City Centre
Price was £953, price is now £485 per person
£485
per person
31 Aug - 4 Sept
found 11 hours ago
Return flight included
Aberdeen (ABZ) to London (LHR)
9/10 Wonderful! (1,607 reviews)
Room service would of been appreciated,breakfast buffet is excellent ,the bar has limited snacks.

Reviewed on 10 Jun 2026

Hotel Riu Plaza London Victoria

Hotel Riu Plaza London Victoria

4 out of 5
London City Centre
Price was £1,007, price is now £520 per person
£520
per person
31 Aug - 4 Sept
found 15 hours ago
Return flight included
Aberdeen (ABZ) to London (LHR)
9/10 Wonderful! (3,753 reviews)
Last minute booking and very pleased

Reviewed on 9 Jun 2026

The Windmill

The Windmill

3 out of 5
Cricklewood
Save 100% on your flight
Price was £535, price is now £288 per person
£288
per person
25 Jul - 28 Jul
found 1 day ago
Return flight included
Glasgow (GLA) to London (LHR)
7.4/10 Good! (425 reviews)
Only a 10 minute walk from the Kilburn station. Very nice hospitality. Was quite, clean and had a lovely stay.

Reviewed on 21 Oct 2025

Miiro Templeton Garden

Miiro Templeton Garden

4 out of 5
London City Centre
Save 100% on your flight
Price was £795, price is now £470 per person
£470
per person
31 Aug - 4 Sept
found 11 hours ago
Return flight included
Aberdeen (ABZ) to London (LHR)
9.6/10 Exceptional! (617 reviews)
The staff was super friendly and helpful. Dinner was amazing. Room and location were perfect.

Reviewed on 6 Jun 2026

Windsor and Maidenhead Essential Information

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

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 £107 per night from 14 Jun to 15 Jun
£107
14 Jun - 15 Jun
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"The cooked breakfast was cold and cold plates This was the only let down for our stay."

Reviewed on 7 Jun 2026

De Vere Beaumont Estate
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 £168 per night from 21 Jun to 22 Jun
£168
21 Jun - 22 Jun
includes taxes & fees
9/10 Wonderful! (1,011 reviews)
"Enjoyed our two nite stay, convenient and centralized location, staff was friendly and helpful, no elevator so bellman had to lug our heavy luggage up the stairs, beautiful view of the Thames from the patio !"

Reviewed on 7 Jun 2026

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 £153 per night from 14 Jun to 15 Jun
£153
14 Jun - 15 Jun
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"The staff very good thank you front desk Louis he’s very good and very helpful. Thank you for all the staff very good and kindness. The room clean and nice. Will come back to stay in this hotel again in the future."

Reviewed on 7 Jun 2026

Castle Hotel Windsor
See all 516 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
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Family Friendly Holidays

Frequently asked questions

How much does a Windsor and Maidenhead travel package cost?
Our Windsor and Maidenhead travel packages, which begin from just £240, are an awesome way to save. Choose your favourite hotels, flights and rental car to create a personalized trip.
If I'm not able to travel, can I cancel my Windsor and Maidenhead travel package?
We get that unexpected stuff happens. If you've booked a Windsor and Maidenhead travel package and have to change or cancel it, we can help. It's always worth having a look at our Customer Service Portal first for information. But generally speaking, if you've taken out your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been more than 24 hours, your airline, hotel or car rental company may impose a charge.
How do I get a cheap travel package to Windsor and Maidenhead?
Combining your hotel and flight with Expedia won't just save precious time — it'll save you dollars too. A Windsor and Maidenhead travel package makes it a cinch to organise your perfect trip. With more than 550 airlines throughout the world to pick from, finding convenient flights that fit your schedule won't be difficult. Not only that, we have over 1,000,000 hotel options globally to pick from. Now that's what we call choice. No matter who you are, Expedia will help show you the world.
Does Expedia offer Book Now, Pay Later Windsor and Maidenhead holidays?
Expedia has teamed up with online lender Klarna to make your next trip easier on the purse strings. Paying by instalment means you can spread the costs of your next big holiday, leaving you with more cash to play with while you're travelling. Klarna has several payment plans to pick from, so you're sure to find one that works with your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: Klarna has easy monthly payment plans that work for all budgets, so you can book that well-earned holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your holiday in multiple transactions.
  • Low deposit holidays: Hitting the "book now" button is easier with this option. Simply put down a small deposit on your escape and then start working on your travel itinerary.

How far in advance should I book my Windsor and Maidenhead holiday?
The earlier you book, the better. Airlines typically release flight tickets nearly 12 months prior to departure, and this is an excellent opportunity to pick up some rock-bottom prices. Boss just told you to use up your holiday time next month? That's fine too — Expedia are never short on fantastic deals to help you have the getaway of your dreams, at a price you can afford.
What does an Expedia Windsor and Maidenhead travel package include?
It's up to you! You can pick from a range of Windsor and Maidenhead packages, such as a hotel, flight and rental car. You can also book a flight with a hotel, or a rental car and a flight. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your Windsor and Maidenhead escape looks like, get set to save!
What should I know before booking a Windsor and Maidenhead travel package?
Our prices are always low. However, you'll score even more bargains when you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and tons of choice.
Can I choose my airline with a Windsor and Maidenhead Expedia travel package?
You can, and with over 550 airlines to select from around the world, you have loads of choice. Have a look through the available options and find out which airline suits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.