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

Central Windsor, Free Parking 300m To Castle, Pet Friendly - Maidenhead
9.3 19 reviews

Central Windsor, Free Parking 300m To Castle, Pet Friendly

apartment, Windsor
This Central Windsor flat offers a prime location, just a 6-minute walk from Windsor Castle and 3.7 kilometres from Legoland Windsor.
This 93 square metre apartment accommodates up to 11 guests, featuring a fully equipped kitchen with a dishwasher and oven, complimentary private parking, and free high-speed WiFi.
Meadow House  Detached  Driveway Parking  Nr Taplow Station W/ Direct Trains To Central London  By Yoko Property - Maidenhead
No reviews

Meadow House Detached Driveway Parking Nr Taplow Station W/ Direct Trains To Central London By Yoko Property

apartment, Maidenhead
This Dorney Reach residence offers a riverside village setting with Dorney Court and the Riverside Marquee a 15-minute walk away, and is an 8-minute drive from Maidenhead.
This 4-bedroom, 2-bathroom house accommodates up to 8 guests and features a fenced garden, driveway parking for 4-5 vehicles, Smart TVs with Netflix, and free super-fast WiFi, with access to walks along the River Thames and Dorney Lake.
Magnolia Penthouse - Maidenhead
9.2 69 reviews

Magnolia Penthouse

apartment, Windsor
This Windsor penthouse is a 9-minute walk from Windsor Castle and 3.5km from Legoland Windsor, offering easy access to major attractions.
The 60 square metre self-catering apartment sleeps seven guests, features two bedrooms, one bathroom, free Wi-Fi, and private parking.
5 Guests | Free Parking | Easy Train To Reading - Maidenhead
10 2 reviews

5 Guests | Free Parking | Easy Train To Reading

apartment
This Maidenhead flat offers a peaceful base in Berkshire, located a 15-minute walk from the town centre and within easy reach of the Elizabeth Line for direct travel to central London, with Windsor and Reading a short drive away.
This two-bedroom apartment accommodates up to five guests, featuring a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside on-site parking and a garden for your convenience.

Best Maidenhead holiday rentals with parking

Crown Mews By Stay Focused Sa - Maidenhead
8.6 65 reviews

Crown Mews By Stay Focused Sa

house, Windsor
Crown Mews, a Windsor holiday home, is a 14-minute walk from Windsor Castle and 3.4km from Legoland Windsor.
This 812 square metre property boasts two bedrooms, one bathroom, sleeps ten guests, and includes a fully equipped kitchen, free Wi-Fi, and a washing machine.
Hampden Apartments - The Diana - Maidenhead
9.2 247 reviews

Hampden Apartments - The Diana

apartment, Windsor
The Hampden Apartments - The Diana is located in Windsor, a 3.2km walk from Windsor Castle and 3.2km from Legoland Windsor. The apartment has received excellent ratings for location, cleanliness, and overall satisfaction.
This one-bedroom flat has a fully equipped kitchen, a private terrace, and a washing machine. Guests can enjoy free Wi-Fi, a satellite flat-screen TV, and free private parking.
2 Bed Retreat Parking Vat Q - By Tempstay - Maidenhead
9.2 7 reviews

2 Bed Retreat Parking Vat Q - By Tempstay

apartment, Windsor
This Windsor apartment is situated 1.9km from Windsor Castle and 2.6km from Legoland Windsor, offering easy access to other attractions such as Dorney Lake and LaplandUK.
This 100 square metre dwelling boasts two bedrooms, two bathrooms, and accommodates up to seven guests, featuring a fully equipped kitchen, garden, allocated parking, free Wi-Fi, and a washing machine.
Spacious Flat In Maidenhead - Maidenhead
No reviews

Spacious Flat In Maidenhead

apartment
This one-bedroom flat in Berkshire offers a private ground floor entrance in a quiet residential area, situated a short 500-meter walk from the town centre and railway station, with a park directly opposite.
This accommodation provides parking, internet, a kitchen, and a capacity for two guests, ideal for exploring the city and for onward travel.

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

Modern 2-bed Near Elizabeth Line & Heathrow - Maidenhead
No reviews

Modern 2-bed Near Elizabeth Line & Heathrow

apartment, Slough
This one-bedroom flat is located in Slough, 19 kilometers from Heathrow Airport and close to the Elizabeth Line.
This modern apartment features a terrace, balcony, free WiFi, a work desk, and a fully equipped kitchen, accommodating up to 15 guests.
Your Place In Windsor With Kitchen And Terrace - Maidenhead
8.7 3 reviews

Your Place In Windsor With Kitchen And Terrace

apartment, Windsor
This Windsor apartment, sleeping up to seven guests, offers a self-catering stay with a private terrace and parking, though its precise location within the town requires further clarification.
The one-bedroom flat includes a fully equipped kitchen, bathroom, and flat-screen TV, providing comfortable accommodation for families or groups visiting Windsor.
2br Ground Floor  Parking  Central By Tempstay - Maidenhead
No reviews

2br Ground Floor Parking Central By Tempstay

apartment, Windsor
This ground floor flat is centrally located in Windsor, offering easy access to Windsor Castle and the Long Walk, both within a 10-minute walk.
The accommodation sleeps up to five guests in two double bedrooms and a sofa bed, featuring two bathrooms, a fully equipped kitchen, free WiFi, and on-site parking.
Charming Cottage In Windsor - Walk To Castle &Shops! - By Tempstay - Maidenhead
8.8 87 reviews

Charming Cottage In Windsor - Walk To Castle &Shops! - By Tempstay

house, Windsor
This charming cottage is just a short walk from Windsor Castle and within easy reach of Legoland Windsor, making it a perfect base for exploring the town and its attractions. The property has received excellent ratings for location, cleanliness, and overall experience.
The cottage has two bedrooms and one bathroom, offering comfortable accommodation for up to four guests. It features a fully equipped kitchen, a private garden, and free parking, ensuring a relaxing and enjoyable stay.

Best Maidenhead holiday rentals with air conditioning

Berkshire Cottage - Wellness Centre - Maidenhead
No reviews

Berkshire Cottage - Wellness Centre

house, Sunninghill
Berkshire Cottage - Wellness Centre is located in Sunninghill, 5.47 kilometres from LaplandUK and 10.46 kilometres from Legoland Windsor.
This wellness centre offers accommodation for up to 19 guests, featuring 1 bedroom, 4 bathrooms, a shared kitchen with a dishwasher and oven, air conditioning, a swimming pool, a terrace, a garden, and parking, with WiFi included.
Luxurious Barn Between Marlow & Henley - Maidenhead
9.9 208 reviews

Luxurious Barn Between Marlow & Henley

apartment
This charming cottage is situated in the picturesque village of Medmenham, just 3km from Marlow and 8km from Henley-on-Thames, offering a peaceful escape amidst beautiful countryside. The property has received excellent ratings for its cleanliness, location, and overall guest experience.
The two-bedroom cottage comfortably accommodates up to four guests, with the option of adding two extra beds. Guests can enjoy a fully equipped kitchen, air conditioning, Wi-Fi, and two parking spaces, as well as a private terrace and garden with direct access to woodland walks and the River Thames.
Lovely Cottage In Beautiful Berkshire Near Ascot - Maidenhead
10 1 review

Lovely Cottage In Beautiful Berkshire Near Ascot

cottage, Warfield
This newly refurbished barn-style cottage, located in Bracknell, offers a rural escape with easy access to Windsor Castle (a short drive), Legoland (a short drive), and Thorpe Park (a short drive), and is situated within 10 kilometers of both the Royal Berkshire Polo Club and Ascot Racecourse.
This 2-bedroom, 1-bathroom property accommodates up to 5 guests, features a secure gated parking with CCTV, and provides direct access to Swinley Forest and Windsor Great Park for outdoor pursuits like cycling and dog walking.
Slough Apartment 
Proximity To 
London & Windsor - Maidenhead
9.2 25 reviews

Slough Apartment Proximity To London & Windsor

apartment
This executive flat in central Slough, Berkshire, is located 24km from Heathrow Airport and a short walk from Slough train station, offering easy access to London and the rest of Berkshire.
The one-bedroom, one-bathroom apartment sleeps three guests and features a fully equipped kitchen with fridge, freezer, microwave, and dishwasher, plus air conditioning, parking, fast Wi-Fi, and a workspace; nearby restaurants and shops provide added convenience.
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