Windsor and Maidenhead holiday lettings

We found 1,917 holiday rentals — enter your dates for availability

Discover a selection of 174 homes, 233 apartments and other holiday rentals in Windsor and Maidenhead that are perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as parking and a washer and dryer. At the end of the day, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts - Windsor and Maidenhead

Showing deals for:14 Nov - 21 Nov

Why visit Windsor and Maidenhead

  • Iconic Windsor Castle: Visit the magnificent residence of the Queen, offering rich history and stunning architecture.
  • Beautiful Thames River: Enjoy scenic walks along the riverbank or take a leisurely boat trip to soak in the picturesque views.
  • Historic Town Centre: Explore the charming streets of Windsor and Maidenhead with quaint shops, cafes, and historic landmarks.
  • Green Spaces: Relax in the lush parks and gardens, perfect for picnics and leisurely strolls.
  • Cultural Events: Experience a variety of local events, festivals, and performances that celebrate the region's vibrant culture.

What do I need to keep in mind when booking a vacation in 'Windsor and Maidenhead

If you’re travelling with a group, with family, bringing your pets, or seeking extended stays, it’s important to filter based on your key priorities. Here are some helpful booking tips for using Vrbo.

  • Traveling to Windsor and Maidenhead with a group: Think about how many bedrooms you require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for these options and much more on Vrbo.
  • Traveling to Windsor and Maidenhead with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Windsor and Maidenhead: For many, a family holiday isn't truly fulfilling unless their furry companion is along for the adventure. If that resonates with you, explore Vrbo properties that welcome pets. Most pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Windsor and Maidenhead: If you're in search of holiday rentals offering discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include preferences such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Booking with Vrbo is a breeze

Are you hoping to save some money on your upcoming journey? Being flexible with your travel dates can be beneficial, as prices tend to vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo accommodation that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's innovative Trip Board offers you a convenient way to plan your journeys, pick up from where you last stopped, or review and arrange your travel plans. You can easily locate your previously saved and booked properties under Potential, Upcoming, or Current Trips. To start using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Find the perfect holiday rental for your Windsor and Maidenhead getaway

Learn about the unique charm of Windsor and Maidenhead with a stay in a holiday home rental. This city has something for everyone. Warner Bros. Studio Tour London and Wembley Stadium are just a couple of the must-see attractions in the area. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in Windsor and Maidenhead

Are you hoping to find attractions to visit while you're in town? Venture out of your cosy holiday rental and experience everything that makes Windsor and Maidenhead a one-of-a-kind holiday spot. Here are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Warner Bros. Studio Tour London (17.3 mi / 27.9 km)
  • LEGOLAND® Windsor (5 mi / 8.1 km)
  • Stanlake Park Wine Estate (6.7 mi / 10.7 km)
  • Lapland UK (7.9 mi / 12.7 km)
  • Coral Reef Bracknells Water World (9.2 mi / 14.8 km)
  • Nirvana Spa (10 mi / 16.1 km)

Exploring the natural landscape of Windsor and Maidenhead

Whether you're an active traveller or just want to spend some time taking in the scenery, Windsor and Maidenhead is a great place to get outside. Here are some of the area’s most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Hyde Park (23.8 mi / 38.4 km)
  • Dorney Lake (3.8 mi / 6.1 km)
  • Windsor Great Park (6.3 mi / 10.1 km)
  • Virginia Water (9.5 mi / 15.3 km)
  • Chiltern Hills (11.2 mi / 18.1 km)
  • Thames Path (11.3 mi / 18.2 km)

Transport options to and around Windsor and Maidenhead

If you're travelling by train, Maidenhead Station, Maidenhead Furze Platt Station and Maidenhead Cookham Station are the main stations in the area.

Frequently asked questions

How much does it cost to rent a holiday rental in Windsor and Maidenhead?
Different things influence how much you'll pay for a holiday rental in Windsor and Maidenhead, including the length of stay, type of property and season. Still, all our holiday homes have one thing in common — unbeatable value. Just enter your travel dates to find your home away from home.
How much does it cost to rent a beach house in Windsor and Maidenhead?
When you travel and the size and style of the property will influence how much you'll pay for your beachside escape. Click on your Windsor and Maidenhead travel dates to see all your options on Vrbo. Looking for basics like WiFi, or perks like a private pool? Use our filters to choose the features and amenities you want in your holiday home.
How old do you have to be to rent a holiday rental in Windsor and Maidenhead?
The minimum age is generally 16, 18 or 21. It can vary across properties on Vrbo, so check the rules of your preferred Windsor and Maidenhead stay before booking.
How long can I rent a holiday rental in Windsor and Maidenhead for?
The amount of time you can book a Windsor and Maidenhead holiday rental for depends on each property. Simply tap in your dates of travel to view options that offer extended stays. They have all you require to make your extended break more comfortable and enjoyable, such as laundries and air conditioning. Some properties may also offer weekly or monthly discounted prices, so you can stay even longer for less.

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