Holiday Rentals in Maidenhead

445 available vacation rental offers

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Maidenhead holiday rentals
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Best Holiday rentals and Airbnb offers in Maidenhead

Best family friendly Maidenhead holiday rentals

Among the 445 accommodations in Maidenhead, here are the 4 best family friendly rentals

3bed 2bath Penthouse Windsor Long Walk By Tempstay - Maidenhead
10 2 reviews

3bed 2bath Penthouse Windsor Long Walk By Tempstay

apartment
This Windsor apartment, minutes from The Long Walk and Eton Bridge, offers stunning Windsor Castle views and is a short drive (approximately 20-30km) from Legoland Windsor and Heathrow Airport.
The two-bedroom, two-bathroom flat sleeps four, features a fully equipped kitchen with dishwasher, dedicated parking, and a private balcony; enjoy easy access to London via direct trains to Waterloo.
Enchanting, Stylish Country Garden Cottage - Maidenhead
9.6 173 reviews

Enchanting, Stylish Country Garden Cottage

apartment
The Old Estate Office is a charming garden cottage located in Hurley, just a short drive from Cliveden House, Dorney Lake, and Legoland Windsor. The cottage has received excellent ratings for location, cleanliness, and overall user experience.
The cottage has two bedrooms and one bathroom, providing comfortable accommodation for up to five guests. Enjoy the peaceful garden, relax on the terrace, and take advantage of amenities including a fully equipped kitchen, free Wi-Fi, and private parking.
Apt - Sleeps 2 - Parking - Wifi - Maidenhead
No reviews

Apt - Sleeps 2 - Parking - Wifi

apartment, Slough
This one-bedroom flat is situated in Slough, just a short distance from the River Thames and within easy reach of popular attractions like LEGOLAND® Windsor and Thorpe Park. The surrounding area offers a mix of residential and commercial properties, providing a convenient location for exploring the region.
The 40 square meter flat comfortably sleeps two guests and features a well-equipped kitchen, a spacious living area, and a modern bathroom. The flat also includes amenities such as free parking, high-speed internet, and a washing machine, making it a great choice for families or couples looking for a comfortable and convenient base in Slough.
Inclusive, Childsafe, Garden, Near Pubs/river/golf - Maidenhead
9.9 162 reviews

Inclusive, Childsafe, Garden, Near Pubs/river/golf

house
This charming cottage is located just a mile from Cookham, in a peaceful rural area close to the River Thames. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage offers a comfortable and modern space for up to four guests, with a galleried bedroom and a fully equipped kitchen. Guests can enjoy a private garden with a BBQ, relax in the jacuzzi or spa, or even play tennis on the court.

Best Maidenhead holiday rentals with parking

Bright & Spacious 3-bed, 2-bath Home In Graylands Close - Maidenhead
8.7 3 reviews

Bright & Spacious 3-bed, 2-bath Home In Graylands Close

house, Slough
This spacious Slough house, located on Graylands Close, is just 7.2km from Dorney Lake, 8km from Legoland Windsor, and 6.6km from Windsor Castle.
The 120 square metre property boasts a 3-bedroom, 2-bathroom layout sleeping up to 13 guests, complete with a fully equipped kitchen, garden, free Wi-Fi, and washing machine.
Ground Floor 2bedroom Apt In Central Slough By Easy 2 Manage - Maidenhead
8.1 7 reviews

Ground Floor 2bedroom Apt In Central Slough By Easy 2 Manage

apartment, Slough
This ground-floor Slough apartment, located in central Berkshire just 13km from London Heathrow Airport, offers convenient access to local amenities and transport links.
The 1000 square metre flat features two bedrooms, one bathroom, and sleeps up to nine guests, boasting free WiFi, private parking, and a fully equipped kitchenette.
Entr - Modern Apartments In Windsor - Maidenhead
8.8 409 reviews

Entr - Modern Apartments In Windsor

apartment, Windsor
These modern apartments are located in Windsor, just 3.2km from Legoland Windsor and 2.6km from Windsor Castle, making them ideal for exploring the town's attractions. They have received excellent ratings for location, cleanliness, and overall user experience.
Each apartment features two bedrooms, a comfortable living area with a sofa and flat-screen TV, and a fully equipped kitchen with a dining area. Enjoy the convenience of a dishwasher, oven, toaster, kettle, and complimentary Wi-Fi, as well as private on-site parking.
 - Maidenhead
No reviews

apartment, Farnham Royal
This one-bedroom flat in Farnham Royal offers convenient access to local amenities and attractions, with a private host ensuring a tailored guest experience for a peaceful stay.
This accommodation for up to three guests includes a kitchen with a fridge and microwave, parking, and internet, and is situated in a location unsuitable for parties.

Frequently asked questions about holiday rentals in Maidenhead

  • What should a first-time visitor not miss in Maidenhead?

    For a first-time visit, you should definitely check out the Maidenhead Heritage Centre, which tells the story of the town. You'll also want to take a stroll along the River Thames and enjoy the views from the beautiful Maidenhead Bridge.
  • What are the best Airbnb and vacation rentals in Maidenhead?

  • Which neighborhood in Maidenhead should you consider for a vacation rental?

    If you're looking for a central location, the area around the High Street is a good choice. It's close to shops, restaurants, and the train station. For a quieter stay, consider the area around Braywick Park, which offers a more peaceful atmosphere.
  • What are the most popular Airbnbs in Maidenhead?

  • What are the top family-friendly attractions in Maidenhead?

    Maidenhead has plenty to keep families entertained. The LEGOLAND Windsor Resort is just a short drive away, while the Dorney Lake is great for watersports and the National Trust's Cliveden is a stunning country estate with beautiful gardens.
  • What are the best vacation rentals with a pool in Maidenhead?

  • When is the best time to book a vacation rental in Maidenhead?

    The best time to book a vacation rental in Maidenhead is during the shoulder seasons, from April to May or September to October. You'll avoid the summer crowds and get better deals.
  • What are the best rentals for families and kids in Maidenhead?

  • What events or festivals should visitors check out in and around Maidenhead?

    Maidenhead hosts the annual Maidenhead River Festival in June, which features live music, boat races, and a funfair. The nearby Windsor Castle also hosts various events throughout the year, including the Changing of the Guard ceremony.
  • What are the best rentals or Airbnbs with a jacuzzi in Maidenhead?

  • What are the best budget-friendly activities in Maidenhead?

    For a budget-friendly day out, head to the Maidenhead Thicket, a beautiful woodland area with walking trails. You can also enjoy a picnic in Braywick Park or take a free guided tour of the Maidenhead Town Hall.
  • What are the best restaurants with local dishes in Maidenhead?

    For a taste of local cuisine, try The Greyhound Inn, which serves traditional pub food. The Crooked Billet is another popular choice, offering a more upscale dining experience with a focus on British ingredients.
  • What are the best walking or cycling routes in Maidenhead?

    The Thames Path National Trail runs through Maidenhead, offering stunning views of the river. For a shorter walk, try the Maidenhead Nature Trail, a circular route through the Maidenhead Thicket. There are also several cycle paths along the river and in the surrounding countryside.
  • Are there pet-friendly attractions in Maidenhead?

    Yes, many attractions in Maidenhead are pet-friendly. Braywick Park is a great place for a walk with your dog, and the Maidenhead Thicket has a dedicated dog walking area.
  • What are the benefits of choosing a vacation rental in Maidenhead?

    Vacation rentals offer more space and privacy than hotels, and often come with added amenities like a kitchen and laundry facilities. They also tend to be more affordable, especially for larger groups.
  • What are the top sports attractions and facilities in Maidenhead?

    Maidenhead is home to the Maidenhead Rugby Club, which plays in the National League 1. The town also has a number of other sports facilities, including the Braywick Leisure Centre, which offers a swimming pool, gym, and fitness classes.

Popular destinations

Best Maidenhead holiday rentals with a balcony

4bed/3bath Retreat Steps From Windsor Castle - Maidenhead
No reviews

4bed/3bath Retreat Steps From Windsor Castle

apartment, Windsor
This Windsor city centre house, a 15-minute walk from King Edward Court Shopping Centre and the River Thames, and within 4.8km of Windsor Castle and LEGOLAND® Windsor, offers convenient access to major attractions and transport links.
This 119 square metre property sleeps nine guests comfortably across four bedrooms and a sofa bed, boasting a fully equipped kitchen with fridge, microwave, and dishwasher, plus a garden and parking.
Hampden Apartments - The Henry - Maidenhead
9.1 243 reviews

Hampden Apartments - The Henry

apartment, Windsor
The Hampden Apartments - The Henry is located just a 2km walk from Windsor Castle and 3.2km from Legoland Windsor, making it a great base for exploring this historic town. Guests consistently rate the apartment excellent for its location, cleanliness, and overall experience.
The apartment is a spacious three-bedroom property that comfortably sleeps six guests. It comes equipped with a fully-equipped kitchen, a terrace, free parking, and a spa, providing everything you need for a relaxing and enjoyable stay.
The Royal Hideaway I Parking - Maidenhead
9.0 36 reviews

The Royal Hideaway I Parking

apartment, Windsor
Loft Living by Lawsons offers a one-bedroom apartment in Windsor, a 12-minute walk from Windsor Castle and 3.5km from Legoland Windsor.
This 51-square-metre flat, sleeping up to 7 guests, features a fully equipped kitchen with dishwasher, a private entrance, free Wi-Fi, and a terrace; nearby attractions include Dorney Lake and Thorpe Park.
Stylish 2 Bed Windsor Home - Sleeps 4 - Driveway Parking - Near Castle & Legoland - Maidenhead
8.0 1 review

Stylish 2 Bed Windsor Home - Sleeps 4 - Driveway Parking - Near Castle & Legoland

house, Windsor
This 2-bedroom residence in Windsor is a 14-minute walk from Windsor Castle and 3.7 kilometres from Legoland Windsor.
This 88 square metre dwelling offers accommodation for up to 7 guests, featuring a fully equipped kitchen with a dishwasher and oven, free Wi-Fi, a private garden, and driveway parking.

Best Maidenhead holiday rentals with air conditioning

Friends & Families | Parking & Ev | Station Nearby - Maidenhead
10 83 reviews

Friends & Families | Parking & Ev | Station Nearby

apartment
This three-bedroom apartment is located in Maidenhead, just a short walk from the town centre and train station, making it easy to explore both London and other charming Berkshire towns. The apartment is situated in a grand Grade II Listed building, adding a touch of historical elegance to your stay.
The apartment comfortably sleeps six guests in its three bedrooms, each with a double bed or two single beds that can be joined. The apartment is fully equipped with modern amenities including a dishwasher, washing machine, and dryer, as well as Wi-Fi, making it ideal for a comfortable and convenient stay.
The Cabin At Ivy Cottage - Maidenhead
10 45 reviews

The Cabin At Ivy Cottage

cabin
This Warren Row log cabin is situated near a 15th-century cottage, 5km from Henley-on-Thames, and conveniently located for access to the Elizabeth Line.
The self-catering retreat offers one bedroom, one bathroom, sleeping up to two guests, and features a kitchen, air conditioning, garden, parking, private patio, and welcome treats; picturesque walks start directly from the property.
3-bed Home, Free Parking, Smart Tv,family & Business Ready - Maidenhead
No reviews

3-bed Home, Free Parking, Smart Tv,family & Business Ready

apartment, Slough
This 3-bedroom holiday flat in Slough offers convenient access, situated a short drive from the River Thames and Thames Path, and within a 12-minute walk of Slough Ice Arena.
This accommodation for 6 guests provides Wi-Fi, air conditioning, and essential toiletries, with nearby attractions including Twickenham Stadium, High Street shopping, and Dorney Lake.
House Sleeps 10 With Parking And Garden - Maidenhead
No reviews

House Sleeps 10 With Parking And Garden

house, Maidenhead
This four-bedroom holiday home in Maidenhead is conveniently located 9.3 kilometres from Dorney Lake and 9.7 kilometres from Cliveden House, with Windsor Castle 11.1 kilometres away and Legoland Windsor 11.4 kilometres away, offering straightforward access to popular attractions.
This 40 square metre property offers accommodation for up to 10 guests, featuring air conditioning, a fully equipped kitchen with a dishwasher and oven, complimentary Wi-Fi, free private parking, and a garden, with London Heathrow Airport 22.5 kilometres away.
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