Windsor and Maidenhead Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Sasa Nikolic

  • 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
Price was £308, price is now £154 per person
£154
per person
29 Aug - 31 Aug
found 1 day ago
Return flight included
Edinburgh (EDI) to London (LHR)
6.6/10 (940 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

The 55 by Le Mirage

The 55 by Le Mirage

4 out of 5
London City Centre
Price was £540, price is now £271 per person
£271
per person
20 Aug - 23 Aug
found 1 day ago
Return flight included
Belfast (BFS) to London (LHR)
9.2/10 Wonderful! (495 reviews)
This was a perfectly situated hotel. It was a 5 min walk from the Bayswater Underground. The Main Street had various eateries. The hotel itself was clean, quiet and had a breakfast area for your choosing at £17. The room we had was for 3 people. The room had a full size bed and a sofa bed. By American standards, it was small, but we made it work. The room itself was spacious. The air conditioning was spot on and came in handy since we were there during a heat wave. Highly recommend.

Reviewed on 26 Jun 2026

Hotel Shepherds Bush London

Hotel Shepherds Bush London

3.5 out of 5
Hammersmith and Fulham
Save 100% on your flight
Price was £304, price is now £165 per person
£165
per person
31 Jul - 2 Aug
found 1 day ago
Return flight included
Glasgow (GLA) to London (LHR)
8.2/10 Very good! (566 reviews)
Lovely little boutique hotel right next to the tube station. Road was clean, beds comfortable. A/C was great as we were there durin heat wave

Reviewed on 28 May 2026

Dorsett Shepherds Bush

Dorsett Shepherds Bush

4 out of 5
Hammersmith and Fulham
Save 100% on your flight
Price was £695, price is now £397 per person
£397
per person
14 Aug - 20 Aug
found 1 day ago
Return flight included
Glasgow (GLA) to London (LHR)
7.8/10 Good! (1,670 reviews)
The property was well maintained.

Reviewed on 27 Jun 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 £1,018, price is now £585 per person
£585
per person
2 Aug - 6 Aug
found 18 hours ago
Return flight included
Aberdeen (ABZ) to London (LHR)
9/10 Wonderful! (3,822 reviews)
Nice new hotel conveniently located a short walk from Victoria station. Spacious room (upgraded to accessible room with an external window). Appreciated the generous breakfast included. Overall a very positive stay, just a few areas to look into: - Bizarre, complicated WiFi login and password written on hotel information sheet by receptionist that didn’t work (tried a few times). Why not use industry standard, such as surname/room number? - soundproofing was ok, we could hear people talking as they walked along the corridor, and luckily no-one either side of us. However, there was a very audible sound of running water behind the walls all night, see possible explanation from google below*. - Breakfast was busy and, while there was plenty of food to help yourself to, and frequent cleaning away of dishes, some of the serving spoons were very greasy from the many hotel guests handling them. Suggest hand sanitisers on entry and more napkins. - The coffee dispensed in the three machines tasted awful. Could have been the milk, or the blend of coffee, water and milk in a cappuccino. I tried two machines, as one looked like it had a decaf label on it. *possible explanation from google: Building Material: Many modern hotels use lightweight PVC drainpipes rather than old-school heavy cast iron. PVC transmits the sound of rushing water, which can sound loud like a "waterfall".

Reviewed on 27 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 26 Jul to 27 Jul
£107
26 Jul - 27 Jul
includes taxes & fees
8.2/10 Very good! (1,004 reviews)
"Please do not contemplate staying here over the summer months, we stayed over royal Ascot weekend and I cannot put into words how hot the rooms and the corridors were it felt really unsafe. They give you a desk fan in the room however this did absolutely nothing for the room temperature. I’m 7 and ..."

Reviewed on 27 Jun 2026

De Vere Beaumont Estate
Sir Christopher Wren Hotel

Sir Christopher Wren Hotel

4 out of 5
Thames Street Windsor England
The price is £168 per night from 12 Jul to 13 Jul
£168
12 Jul - 13 Jul
includes taxes & fees
9.2/10 Wonderful! (1,003 reviews)
"I moved out of a hotel in Marlow to this because it had no ac and was like being in an oven. C Wren had basic ac but effective and welcome"

Reviewed on 27 Jun 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 £80 per night from 26 Jul to 27 Jul
£80
26 Jul - 27 Jul
includes taxes & fees
7.4/10 Good! (491 reviews)
"The room overlooked Windsor castle which was amazing. The problem was the room was an oven. The supplied cooling unit was useless and it was unbearable to be in the room, trying to sleep.was almost impossible. The staff were lovely"

Reviewed on 27 Jun 2026

Harte and Garter
See all 524 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 £154, 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.