Windsor and Maidenhead Holidays

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Top Flight + Hotel Deals in Windsor and Maidenhead

Price found within the past 48 hours. Click for updated prices.
OYO Abbey Hotel, London Shepherd's Bush Market

OYO Abbey Hotel, London Shepherd's Bush Market

3 out of 5
Hammersmith and Fulham
Price was €213, price is now €130 per person
€130
per person
22 Nov - 24 Nov
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
7.4/10 Good! (165 reviews)
Very comfortable beds and an ideal location, bathrooms on the small side and need replacing. The staff were very friendly. I would stay here again.

Reviewed on 24 Nov 2024

Byron Hotel London

Byron Hotel London

3.5 out of 5
London City Centre
Price was €615, price is now €364 per person
€364
per person
17 Oct - 20 Oct
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
8.8/10 Excellent! (339 reviews)
The elevator was out of order and our room was on the fifth floor, and the stairways become progressively narrow as you go up, very hard to negotiate with luggage. The room was not much bigger than a broom closet. Though claustrophobic, it was nicely decorated and maintained, and staff were nice. We got the room at a reduced last-minute price; its normal price is far too high for the size of the room.

Reviewed on 24 Aug 2025

The Villa Kensington

The Villa Kensington

3.5 out of 5
London City Centre
Price was €304, price is now €180 per person
€180
per person
20 Oct - 22 Oct
found 11 hours ago
Return flight included
Dublin (DUB) to London (LHR)
8/10 Very Good! (900 reviews)
The rooms are small but clean and adequate and within walking distance of Gloucester Road tube station. Very convenient also for local amenities.

Reviewed on 17 Aug 2025

The Bryson Hotel

The Bryson Hotel

4 out of 5
London City Centre
Price was €497, price is now €302 per person
€302
per person
17 Oct - 20 Oct
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
7.8/10 Good! (513 reviews)
Nice, quiet and pleasant room and location. Friendly staff

Reviewed on 17 Aug 2025

Leman Locke

Leman Locke

4 out of 5
London City Centre
Save 100% on your flight
Price was €649, price is now €396 per person
€396
per person
23 Oct - 26 Oct
found 1 day ago
Return flight included
Dublin (DUB) to London (LHR)
9.2/10 Wonderful! (1,000 reviews)
convenient kitchen and laundry facilities dinning options are limited in the area

Reviewed on 26 Jun 2025

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 €130 per night from 28 Aug to 29 Aug
€130
28 Aug - 29 Aug
includes taxes & fees
7.8/10 Good! (1,013 reviews)
"One thing the swimming pool area could be cleaner and more efficient"

Reviewed on 24 Aug 2025

De Vere Beaumont Estate
Castle Hotel Windsor

Castle Hotel Windsor

4 out of 5
18 High Street, Windsor, England
The price is €138 per night from 28 Aug to 29 Aug
€138
28 Aug - 29 Aug
includes taxes & fees
9/10 Wonderful! (1,008 reviews)
"Great location, directly opposite the castle, parking is a bit expensive at £30 for 24hours. No facilities"

Reviewed on 25 Aug 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 €179 per night from 31 Aug to 1 Sept
€179
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
"Lovely hotel in a great position. Comfy beds and clean rooms. Staff were really helpful and very polite."

Reviewed on 24 Aug 2025

Sir Christopher Wren Hotel
See all 529 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 €130. 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.