Windsor and Maidenhead Holidays

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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.
The Windmill

The Windmill

3 out of 5
Cricklewood
Save 100% on your flight
Price was £524, price is now £275 per person
£275
per person
25 Jul - 28 Jul
found 1 day ago
Return flight included
Glasgow (GLA) to London (LHR)
7.4/10 Good! (424 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

Hotel La Place

Hotel La Place

3.5 out of 5
London City Centre
Price was £629, price is now £319 per person
£319
per person
20 Jul - 23 Jul
found 5 hours ago
Return flight included
Glasgow (GLA) to London (LHR)
8.4/10 Very Good! (464 reviews)
Great location close to Tube and lots of restaurants and shops in the area.

Reviewed on 7 May 2026

Hotel Riu Plaza London The Westminster

Hotel Riu Plaza London The Westminster

4 out of 5
London City Centre
Save 100% on your flight
Price was £619, price is now £330 per person
£330
per person
17 Jun - 19 Jun
found 1 day ago
Return flight included
Aberdeen (ABZ) to London (LHR)
9/10 Wonderful! (1,507 reviews)
Would def stay here again. Each walking distance to the Westminster Tube station. Lovely hotel, modern, clean and friendly and helpful staff. Breakfast was really good, loads to choose from. Room was clean and spacious.

Reviewed on 11 May 2026

Dao by Dorsett North London

Dao by Dorsett North London

4 out of 5
Haringey
Price was £1,003, price is now £537 per person
£537
per person
14 Jul - 21 Jul
found 1 day ago
Return flight included
Glasgow (GLA) to London (LHR)
9.6/10 Exceptional! (14 reviews)
Staff at the hotel were exceptionally helpful. The room was very clean and well equipped for self catering- although we did not need this. Location is great for Crouch End and also convenient to access central London.

Reviewed on 1 May 2026

Hotel Riu Plaza London Victoria

Hotel Riu Plaza London Victoria

4 out of 5
London City Centre
Save 100% on your flight
Price was £725, price is now £405 per person
£405
per person
2 Aug - 5 Aug
found 1 day ago
Return flight included
Aberdeen (ABZ) to London (LHR)
9/10 Wonderful! (3,626 reviews)
Friendly staff and good breakfast selection.

Reviewed on 12 May 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 £99 per night from 26 May to 27 May
£99
26 May - 27 May
includes taxes & fees
8/10 Very Good! (1,009 reviews)
This hotel is extremely big; many rooms are in flat-style blocks that feel disjointed from the main hotel, but it's good for big events. The drinks are at a high premium rate but the staff lack knowledge of how they should be served. The pool is family-friendly, so it's not good for couples looking ...

Reviewed on 4 May 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 £179 per night from 25 May to 26 May
£179
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (1,018 reviews)
Great place to stay, really comfortable

Reviewed on 12 May 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 £71 per night from 28 May to 29 May
£71
28 May - 29 May
includes taxes & fees
7.6/10 Good! (429 reviews)
The room was clean but the decor and condition outdated and poor. There appears to have been no updating or redecorating since I last stayed here 10 years ago. No breakfast as they no longer have dining facilities.

Reviewed on 12 May 2026

Harte and Garter
See all 519 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
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 £275, 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.