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Windsor and Maidenhead holiday homes

We found 1,944 holiday rentals — enter your dates for availability
Discover a selection of 53 homes, 43 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:30 Oct - 6 Nov

Image gallery for Luxury barn with pool and spa pool

Garden view of house
10 out of 10, Exceptional, (13 reviews)
Exceptional
(13 reviews)

Luxury barn with pool and spa pool

Maidenhead

6% off
Price is NZ$34,100
for 7 nights, 1 home
NZ$4,871 per night
includes taxes & fees
Luxury barn with pool and spa pool

Find spaces that suit your style

Why visit Windsor and Maidenhead

  • Royal Heritage: Windsor and Maidenhead offer a deep dive into the royal history of England, with historic landmarks and palatial architecture.
  • Scenic Riverside Walks: Enjoy leisurely strolls along the picturesque Thames, taking in the natural beauty and charming views.
  • Vibrant Local Culture: Explore lively neighbourhoods filled with traditional markets, art galleries and quaint local establishments.
  • Seasonal Festivals: Experience a range of community festivals celebrating heritage, food, and music.
  • Heritage Gardens: Wander through beautifully landscaped gardens and serene parks steeped in history.

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

Whether you're travelling with a group, as a family, with your pets, or planning an extended stay, ensure you apply the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Windsor and Maidenhead with a group: Consider how many bedrooms you'll require, along with conveniences like a fully equipped kitchen or an outdoor area for a group get-together. Luckily, you can easily refine your search on Vrbo to include all these features and more.
  • Traveling to Windsor and Maidenhead with young kids: Traveling with little ones can be a challenge. You need to make sure they’re comfortable and safe, with amenities suited to their age, like a private pool. It’s also worth considering how close you are to attractions that cater to families.
  • Taking your pets with you to Windsor and Maidenhead: For many families, a holiday isn't truly special without their furry companions. If that resonates with you, take a look at Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels completely at home.
  • Planning for a long term stay visiting Windsor and Maidenhead: If you’re after holiday rentals offering discounts for month-long stays or more, you’ve come to the right spot. Use the appropriate filters to quickly locate and secure savings on monthly rentals, and don’t forget to include extras like a parking space, a well-equipped kitchen, or a private pool in your search.

Booking with Vrbo is simple

Looking to save on your next holiday? Being flexible with your travel dates can really help, as prices often change. Plus, opting for a longer stay might unlock even better deals. To find the ideal Vrbo property that fits your budget, take advantage of our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo’s Trip Board offers a handy space to start new trips, continue planning where you last left off, or organise your itinerary. You can easily locate properties you’ve saved or booked, which are neatly sorted into Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.bookabach.co.nz/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. Wembley Stadium and LEGOLAND® Windsor 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:

  • LEGOLAND® Windsor (5 mi / 8.1 km)
  • Warner Bros. Studio Tour London (17.3 mi / 27.9 km)
  • Stanlake Park Wine Estate (6.7 mi / 10.7 km)
  • Bekonscot Model Village (7 mi / 11.3 km)
  • Royal Ascot Golf Club (7.7 mi / 12.3 km)
  • Lapland UK (7.9 mi / 12.7 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)
  • West Wycombe Park (9 mi / 14.5 km)
  • Virginia Water (9.5 mi / 15.3 km)
  • Colne Valley Regional Park (10.4 mi / 16.7 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 home in Windsor and Maidenhead?
Different things influence how much you'll pay for a holiday home 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 Bookabach. 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 home in Windsor and Maidenhead?
The minimum age is generally 16, 18 or 21. It can vary across properties on Bookabach, so check the rules of your preferred Windsor and Maidenhead stay before booking.
How long can I rent a holiday home in Windsor and Maidenhead for?
The amount of time you can book a Windsor and Maidenhead holiday home 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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