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Holidays to Maidenhead

Choose two or more items and save on your trip:

Accommodation, flights, car rentals, things to do and more - for your holiday in Maidenhead choose Expedia! Find everything you need to organise your trip to Maidenhead in one place. Enter your dates in the search bar above or scroll to our top deals below!

Top Hotel Deals

5 out of 5
The price is £620 per night from 3 Jun to 3 Jun
This family-friendly Maidenhead hotel is located near the airport, 0.5 mi (0.8 km) from Cliveden House, and within 6 mi (10 km) of Bekonscot Model Village and ...
4.6/5Exceptional! (142 reviews)
"We absolutely loved it here. It was so peaceful even with people in the grounds that were not in the hotel. Highly recommend it."

Reviewed on 17 Aug 2020

Crazy Fox Hurley Boutique Bed & Breakfast
Crazy Fox Hurley Boutique Bed & Breakfast
5 out of 5
The price is £130 per night from 17 May to 17 May
Situated in Maidenhead, this luxury hotel is within 3 miles (5 km) of Bisham Abbey, Higginson Park and All Saints Church. Longridge Activity Centre is 3 mi (4.9 ...
4.7/5Exceptional! (78 reviews)
Perfect relaxing getaway
"We checked in at the Crazy Fox using the keyless system with no problems. We loved the room especially the huge bed. The room was modern, but cosy and very clean. There were some lovely little touches, including a torch if we wanted to go out in the evening. Due to covid-19 virus we were not able ..."

Reviewed on 1 Sep 2020

Crazy Fox Hurley Boutique Bed & Breakfast
Monkey Island Estate
Monkey Island Estate
5 out of 5
The price is £208 per night from 18 May to 18 May
Situated on the riverwalk, this luxury hotel is 0.8 mi (1.4 km) from Bray Marina and 2.4 mi (3.9 km) from Dorney Lake. Windsor Racecourse and Bird Hills Golf ...
4.7/5Exceptional! (15 reviews)
Highly recommend
"Just a perfect piece of rural England...beautiful staff, beautiful food & an idyllic location."

Reviewed on 23 Mar 2020

Monkey Island Estate
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.

The Advantages of Maidenhead Weekend Breaks

Discover a different side of the British Isles with a weekend break in Maidenhead. Take short breaks away from home and enjoy some quality time in a beautiful place. You’ll come back feeling refreshed and inspired. You can have an action-packed Maidenhead weekend break or get some peace with a relaxing holiday. Whatever experience you’re looking for, find it with our deals on hotels in Maidenhead.

Cheap Weekend Breaks to Maidenhead

There are lots of ways to take cheap weekend breaks to Maidenhead. Expedia offers deals on car hires and hotel rooms and covers trips for all kinds of travellers. The best way to save is with our holiday packages in Maidenhead. First, choose your car hire and hotel reservation. Then we’ll bundle them together into one discounted price. Solo explorers, couples, families, and groups of friends can discover budget solutions for their weekend breaks. Once you arrive, enjoy some of the fun things to do, many of which are free or cheap to experience  

Maidenhead Romantic Weekend Breaks

Couples love taking romantic weekend breaks in Maidenhead. Whisking your lover away for a romantic Maidenhead weekend break is the perfect opportunity to make new memories together. Expedia offers all kinds of hotel options, so you can find romantic hotels in Maidenhead and choose the best place for you. Check out our deals on beautiful properties, and you’ll save even more when you choose to package your hotel reservation with a car hire. 

Family Weekend Breaks in Maidenhead

Set some time aside to experience family weekend breaks in Maidenhead. There are plenty of excellent family-friendly hotels in Maidenhead within our selection of hotels. You can also find a place to call home in one of the holiday rentals in Maidenhead. With accommodation, activities, and adventure all waiting, there’s never been a better time to plan Maidenhead family weekend breaks. 

Plan your Maidenhead holiday with Expedia

  • Book your 2021 holiday package deals now! Buy your accommodation, flight or car together and get extra savings on your next trip!
  • We have selected for you amazing deals on incredible hotels in Maidenhead. Have a look simply by using the search bar above.
  • Most hotels come with free cancellation, because we believe that flexibility matters now more than ever!

For more information, visit our COVID-19 information page
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*Some hotels require you to cancel at least 24-48 hours before check-in.

Frequently asked questions