Maidenhead holiday lettings

We found 949 holiday rentals — enter your dates for availability
Discover a selection of 32 homes, 29 apartments and other holiday rentals in Maidenhead that are perfect for your trip. Whether you’re staying in a holiday home with family, friends or just your furry companion, you'll find the amenities that you need and want, which might include Wi-Fi and a washer and dryer. No matter what you're looking for, you're sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

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Why visit Maidenhead

  • Picturesque River Thames: Enjoy scenic strolls along the River Thames, where the iconic Maidenhead Bridge showcases the town's rich history.
  • Historic houses: Explore charming historic houses that reflect Maidenhead's architectural heritage and cultural significance.
  • Family-friendly parks: Relax in vibrant local parks, perfect for leisurely days with family amidst lush greenery.
  • Vibrant local markets: Immerse yourself in the warm atmosphere of local markets, offering a taste of the community's culture.
  • Welcoming neighbourhoods: Discover the friendly locals and charming streets, making Maidenhead an inviting base for exploration.

Popular types of accommodation in Maidenhead

Maidenhead, nestled in the picturesque Royal Borough of Windsor and Maidenhead, offers a delightful array of holiday homes, from charming cottages to modern apartments and private vacation rentals. Visitors can explore local attractions such as the scenic River Thames, historical landmarks, and lush parks. With excellent amenities and a warm, welcoming atmosphere, you’re sure to enjoy a memorable stay in this vibrant town.

  • Flats: The top choice for holiday stays in Maidenhead, offering modern amenities and city-centre locations.
  • Private Homes: These self-contained residences provide a homely atmosphere, ideal for families and groups.
  • Cottages: Quaint and charming, these properties offer a cosy retreat in scenic surroundings.
  • Guest Houses: A welcoming option, providing personal service and a comfortable stay.
  • Chalets: Perfect for those seeking a unique getaway experience in a tranquil setting.**

Top attractions in and around Maidenhead

Maidenhead, England, offers a delightful blend of outdoor activities and cultural experiences perfect for family vacations. Visitors can explore historic houses, enjoy leisurely days at local parks, or admire the stunning architecture of churches. The town's attractions provide ample opportunities for families to engage with the rich history and scenic landscapes, ensuring a memorable visit filled with exploration and enjoyment.

  • Cliveden House: This magnificent historic house offers a glimpse into England's rich past, set amidst stunning gardens and parkland. Experience luxurious accommodation, fine dining, and a tranquil atmosphere, perfect for a relaxing getaway.
  • LEGOLAND® Windsor: A fantastic theme park featuring interactive rides and attractions designed for families. Enjoy a day filled with creativity and fun, with themed areas that bring LEGO bricks to life.
  • Windsor Castle: A majestic royal residence that boasts impressive architecture and beautiful grounds. Explore its rich history, stunning interiors, and the enchanting atmosphere that surrounds this iconic landmark.

Things to do recommended for couples

Discover the charm of Maidenhead with a romantic riverside walk along the Thames, followed by a delightful meal at a quaint restaurant. Don't miss a scenic boat trip, offering stunning views of the countryside, perfect for a couple's escape.

Things to do recommended for families

Families will delight in the scenic beauty of Maidenhead, exploring the lush parks such as Kidwells Park or enjoying a boat trip along the River Thames. The vibrant Maidenhead Heritage Centre offers engaging activities for children, ensuring a memorable and enriching experience for all ages.

Things to do recommended for groups

Experience the thrill of motorsport at Mercedes-Benz World, only 26km from Maidenhead. For an adventurous day, tackle the zipline courses at Go Ape in Bracknell (14km away) or enjoy the scenic heights at Go Ape in Wendover Woods (29km away).

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When travelling with a group, family, pets, or planning extended stays, it's essential to prioritise your preferences when filtering options. Here are some helpful booking tips for Vrbo to assist you.

  • Traveling to Maidenhead with a group: Think about the number of bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor space for group gatherings. Thankfully, you can easily filter for all these options, and much more, on Vrbo.
  • Traveling to Maidenhead with young kids: Travelling with young children can be quite demanding. It’s important to prioritise their comfort and safety, as well as to look for age-appropriate facilities, 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 Maidenhead: For many, a family holiday wouldn’t feel complete without their furry companion by their side. If this 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 everyone feels comfortable and at home.
  • Planning for a long term stay visiting Maidenhead: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the perfect place. By using the appropriate filters, you can effortlessly discover and save on monthly accommodations. Don't forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay near Maidenhead

Maidenhead, England, offers a delightful blend of outdoor activities and cultural experiences. Stroll along the picturesque River Thames, where the iconic Maidenhead Bridge stands as a testament to the town's rich history. Enjoy family-friendly parks and vibrant local markets, immersing yourself in the warm, welcoming atmosphere. With its charming streets and friendly locals, Maidenhead is an ideal base for exploring the tranquil riverside and experiencing the best of English culture and recreation.

  • Windsor: Located 8km from Maidenhead, Windsor is a charming city renowned for its rich history and cultural attractions. Visitors flock to Windsor for family-friendly outings, outdoor adventures, and cultural experiences. The iconic Windsor Castle, a residence of the Royal Family, is a must-see, along with the beautiful Windsor Great Park and the thrilling Legoland Windsor Resort. The city also offers a vibrant shopping area and several golf courses, making it an ideal destination for both relaxation and entertainment.
  • West Drayton: Situated 18km from Maidenhead, West Drayton is a lively city that combines urban flair with cultural depth. It’s a great spot for families and those seeking a taste of city life. The area is home to various shopping facilities, theatres, and educational institutions, making it perfect for all ages. Notable attractions include the symbolic landmark of St. Martin's Church and local sports facilities. West Drayton serves as an excellent base for exploring the surrounding areas and enjoying the vibrant local scene.
  • Slough: Just 10km from Maidenhead, Slough offers a mix of family-friendly activities, cultural highlights, and entertainment options. Known for its bustling shopping areas and golf courses, Slough attracts visitors with its diverse attractions, including the nearby theme park and historic castles. The city’s symbolic landmarks add to its charm, providing a vibrant atmosphere for both residents and tourists. Whether you're looking to shop, play golf, or simply enjoy the local culture, Slough is a fantastic addition to your itinerary.

Best time to go to Maidenhead

If you're planning a trip to Maidenhead, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January39.9°F (4.4°C)Light RainMostly CloudyAverageSlightly Low
February41.0°F (5.0°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
March44.2°F (6.8°C)No Rain (Dry)Mostly CloudyAverageSlightly Low
April48.6°F (9.2°C)No Rain (Dry)Mostly CloudySlightly HighAverage
May54.0°F (12.2°C)Light RainMostly CloudyAverageAverage
June60.1°F (15.6°C)Light RainMostly CloudySlightly HighSlightly High
July63.9°F (17.7°C)Light RainMostly CloudySlightly HighAverage
August63.1°F (17.3°C)Light RainMostly SunnyAverageSlightly High
September59.2°F (15.1°C)No Rain (Dry)Mostly SunnyAverageAverage
October53.4°F (11.9°C)Light RainMostly CloudySlightly LowAverage
November46.4°F (8.0°C)Light RainMostly CloudySlightly LowAverage
December42.3°F (5.7°C)Light RainMostly CloudySlightly LowSlightly High

Booking with Vrbo is a breeze

Are you hoping to save on your next getaway? Being flexible with your travel dates can be beneficial, as prices often vary. Additionally, opting for an extended stay typically allows for significant savings. To discover the ideal Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's Trip Board offers a helpful platform for organising your travel plans. You can easily create new trips, resume your previous arrangements, or review your itineraries. All your saved or booked properties are neatly sorted into categories: Potential, Upcoming, and Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Head to the friendly city of Maidenhead

The area's monuments and culture are just some of the reasons to come on holiday to Maidenhead. Travellers to this welcoming city praise the riverfront, bars and restaurants. LEGOLAND® Windsor and Warner Bros. Studio Tour London are just a couple of the must-see attractions in the area. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Maidenhead

Are you looking for top things to see and do while you're in town? Venture out of your cosy holiday rental and experience everything that Maidenhead has to offer. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • LEGOLAND® Windsor (5 mi / 8.1 km)
  • Warner Bros. Studio Tour London (17.4 mi / 28 km)
  • Stanlake Park Wine Estate (6.6 mi / 10.6 km)
  • Bekonscot Model Village (7.1 mi / 11.4 km)
  • Liquid Leisure (7.2 mi / 11.6 km)
  • Lapland UK (7.9 mi / 12.7 km)

Exploring the natural landscape of Maidenhead

Whether you're looking for exciting outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Maidenhead. Here are a few of the area's most stunning sights, all within 30 miles (48.2 km) of the city centre:

  • Dorney Lake (3.9 mi / 6.2 km)
  • Windsor Great Park (6.3 mi / 10.2 km)
  • Savill Garden (8.3 mi / 13.4 km)
  • Dinton Pastures Country Park (8.7 mi / 14 km)
  • West Wycombe Park (9 mi / 14.5 km)
  • Virginia Water (9.6 mi / 15.4 km)

Transport to and around Maidenhead

The nearest airport is in Heathrow Airport (LHR), located 12.2 mi (19.7 km) from the city centre. If you can't find a flight that's convenient for your trip, you might consider flying into Farnborough (FAB), which is 17.3 mi (27.8 km) away.

If you prefer to travel by train, Maidenhead Station, Maidenhead Furze Platt Station and Taplow Station are the main stations that serve the city.

Frequently asked questions

What is the best area to stay in Maidenhead when booking a holiday rental?
When considering a holiday rental in Maidenhead, a popular area to stay is the town centre. This vibrant locale is conveniently located near a variety of shops, restaurants, and cafés, making it an ideal base for exploring the area. The proximity to Maidenhead's train station is particularly advantageous for those wishing to travel into London or explore the surrounding towns.

Another excellent choice is the area along the River Thames, which offers picturesque views and a lovely setting for leisurely strolls. The riverbank is a delightful spot, especially near the iconic Maidenhead Bridge, and it provides access to scenic walks and recreational activities. You can also enjoy the nearby Desborough Island, which is superb for a relaxing day out.

Each of these neighbourhoods has a selection of properties available for holiday rentals, suiting various preferences and budgets.
How much does it cost to rent a holiday home in Maidenhead?
Prices for holiday rentals in Maidenhead vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Maidenhead to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Maidenhead holiday house rentals?
You can find great discounts on house rentals in Maidenhead on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of holiday rental accomodation in Maidenhead?
In Maidenhead, apartments are the most popular type of holiday rental, with around 120 available throughout the town. These apartments are typically located near the picturesque River Thames and the vibrant town centre, offering guests easy access to local shops, restaurants, and parks. Most units come equipped with modern amenities, including fully equipped kitchens, comfortable living areas, and often a private balcony or terrace, providing a great spot to relax after a day of exploring.

Additionally, there are approximately 112 holiday houses available, which cater well to families or larger groups. These homes usually feature multiple bedrooms, spacious living areas, and private gardens, allowing guests to enjoy a bit more space and comfort during their stay. While there are also about 16 cottages in the area, these are less common and provide a quaint, traditional feel, often set in quieter neighbourhoods.
Are there any family house rentals in Maidenhead?
In Maidenhead, there are numerous family-friendly house rentals available, with around 27 options for visitors to choose from. The town features a variety of neighbourhoods, such as the vibrant town centre and the quieter residential areas, all of which provide easy access to local attractions. Many of these properties boast spacious living areas, fully equipped kitchens great for family meals, and outdoor spaces where children can play safely.

Guests can explore nearby points of interest like the beautiful Maidenhead Bridge, which offers scenic views along the River Thames, or visit the lush green spaces of Kidwells Park, ideal for picnics and outdoor activities. Additionally, families can enjoy the local attractions, including the historic Cliveden House and its stunning gardens, which are just a short drive away.
Can I rent a holiday home with a pool or hot tub in Maidenhead?
In Maidenhead, there are several holiday homes available for rent that feature pools and hot tubs, making it an attractive option for those seeking relaxation and leisure during their stay. This charming town, located along the River Thames, offers a mix of modern amenities and historical charm. Many properties in the area come with private pools, outdoor seating areas, and well-equipped kitchens, great for families or groups looking to enjoy a comfortable and enjoyable holiday.

The neighbourhoods around Maidenhead, such as Taplow and Cookham, also provide a scenic backdrop, with opportunities to explore local parks and riverside walks. Additionally, some rentals may include extra amenities like barbecue facilities or garden spaces, enhancing the outdoor experience.
Can I find long-stay holiday rentals in Maidenhead?
A long-stay holiday rental in Maidenhead is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Maidenhead?
In Maidenhead, there are numerous pet-friendly house rentals available, making it an excellent choice for travellers looking to bring their furry companions along. The area offers a variety of properties, from contemporary townhouses to charming cottages, many of which feature amenities such as spacious gardens, modern kitchens, and comfortable living areas.

One of the highlights of staying in Maidenhead is its proximity to several parks and green spaces that are ideal for walking dogs. The beautiful Maidenhead Thicket, with its woodland trails, is a short drive away and provides a lovely natural setting for outdoor adventures. Additionally, the nearby Ray Mill Island features scenic walking paths and picnic spots, allowing for enjoyable outings with pets.
Are there any remote work holiday rentals in Maidenhead?
In Maidenhead, there are numerous options for remote work holiday rentals, with around 188 properties available. The town offers a good blend of modern amenities and scenic surroundings, making it an ideal spot for those looking to work remotely. Many rentals come equipped with high-speed internet and Wi-Fi, ensuring that you can stay connected during your stay.

Properties often feature dedicated office spaces or comfortable work areas, allowing for productive work environments. Additionally, you can expect amenities such as comfortable living areas and full kitchens, making it easy to settle in.

Maidenhead is well-connected to London and offers access to lovely parks and the beautiful River Thames nearby, providing great opportunities for relaxation after a day of work. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Maidenhead holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Maidenhead with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Maidenhead?
In Maidenhead, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals comfortably. Many properties offer onsite parking, making it convenient for those travelling by car. Additionally, travellers can expect coffee and tea makers for their morning brews, as well as access to gardens where they can relax outdoors. Some rentals are also pet-friendly, accommodating those who wish to bring their furry friends along.
When is the best time to visit Maidenhead for a holiday rental?
The best time to visit Maidenhead for a holiday rental is during the peak season from May to July, with July being particularly popular among travellers. This period is characterised by vibrant outdoor activities as the weather warms up, making it ideal for exploring the picturesque surroundings and enjoying events along the River Thames.

During these months, visitors can expect pleasant temperatures ranging from 15 to 25 degrees Celsius, superb for leisurely strolls and sightseeing. The lush parks and gardens come alive, offering beautiful spots for picnics and relaxation. Additionally, the town hosts various local events and festivals, enhancing the lively option and providing a chance to immerse yourself in the community.

For those looking for a more budget-friendly option, December can be a charming time to visit. During this time and cooler, with temperatures averaging around 0 to 5 degrees Celsius, you can enjoy the festive decorations and local holiday markets, which add a unique charm to the town.

Ultimately, the best time to book a holiday rental in Maidenhead depends on whether you prefer the buzz of summer activities or the cosy, festive vibe of winter.
How early should I book a Maidenhead holiday rental?
Book your Maidenhead holiday rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Maidenhead?
In Maidenhead, visitors can enjoy a variety of attractions that highlight the town's charm and natural beauty. One of the main draws is the scenic River Thames, where you can stroll along the riverside, take boat trips, or relax in one of the riverside parks. The Longridge Activity Centre, located nearby, offers outdoor pursuits like kayaking and climbing, appealing to adventure enthusiasts.

The historic Maidenhead Railway Bridge, designed by the famous engineer Isambard Kingdom Brunel, is an iconic landmark that showcases the town's rich transportation history. Additionally, the nearby Taplow Court provides beautiful gardens and a peaceful atmosphere for those looking to unwind.

For shopping and dining, the town centre features a mix of high street brands and independent boutiques, alongside a selection of cafes and restaurants that cater to various tastes.
Can I change or cancel my Maidenhead home rental booking on Vrbo?
To find Maidenhead holiday rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Maidenhead holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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