Holiday Homes in Windsor and Maidenhead

It might be best to get a rental house in when the weather is ideal for enjoying local surroundings. If you go during the off-season months, there might be fewer tourists and often lower rates, like in .

Choose from 169 beautiful holiday homes in Windsor and Maidenhead for your getaway.

You can find perfect holiday homes in Windsor and Maidenhead for as low as £374 per night. Holiday home prices vary depending on what time of year you visit, whether the home is in the city centre or near popular sightseeing spots, and what kinds of amenities it offers.

Find the best deals on Windsor and Maidenhead holiday homes by entering dates and the number of travellers in the search bar. You can use the map feature to view prices and more specific locations of several accommodations all at once. Or filter your search results by star rating, price, number of bedrooms, types of amenities, and accessibility features—Expedia offers incredible deals for every budget.

There’s no better way to spend your well-earned holiday than in a private, cosy Windsor and Maidenhead holiday home. You’ll be able to fit all travellers in your group and have a place to call home while you explore Windsor and Maidenhead.

Depending on your budget and the neighbourhood you choose, you’ll find amenities like a private pool, hot tub, free parking, a full-service kitchen or kitchenette, in-home laundry and WiFi. Your Windsor and Maidenhead holiday won’t be complete without a beautiful view and easy access to popular activities, use our filter to browse our offers.

With Expedia, you’ll earn points on every booking and get incredible deals and member prices. Choose from a vast inventory of holiday homes in Windsor and Maidenhead—and book all your travel in one place. Save even more when you bundle your bookings together. Add a Windsor and Maidenhead car hire to your holiday property into a holiday package.

We suggest using the “free cancellation” filter during your search to make sure your booking is flexible. Some accommodations accept and refund cancellations within a specific timeframe, while others may be non-refundable. Before you book, check your rental terms, or reach out to our customer service portal for further assistance.