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

Relaxing Central Windsor Getaway For Families - By Tempstay - Maidenhead
9.8 6 reviews

Relaxing Central Windsor Getaway For Families - By Tempstay

house, Windsor
This Windsor residence is a 10-minute walk from Windsor Castle and 3.4 kilometres from Legoland Windsor.
This family-friendly house offers 100 square metres of living space with 3 bedrooms, 1 bathroom, a garden, terrace, and parking, plus it is conveniently located near Thorpe Park (12.1 km) and LaplandUK (11.7 km).
Smart Loft Annex In Cookham - Maidenhead
9.8 134 reviews

Smart Loft Annex In Cookham

apartment
This first-floor apartment is located on a quiet lane just a few minutes' walk from Cookham High Street, with its many pubs and restaurants, and is also within easy reach of the River Thames towpath. The apartment has received excellent ratings for its location, cleanliness, and user experience.
This loft annex can accommodate up to 3 guests and features a private entrance, a dedicated parking space, and comfortable furnishings. The apartment offers a range of amenities, including SkyTV with Sky Cinema, Sky Kids, Sky/BT Sports, fast Wi-Fi, and a sheltered lawn area with a table and benches for alfresco dining.
New Modern Eco-friendly 'Loft' With Free Parking. - Maidenhead
9.7 55 reviews

New Modern Eco-friendly 'Loft' With Free Parking.

house
This family-friendly studio apartment in Eton Wick, Berkshire, is ideally located near Windsor Castle and Eton College, offering easy access to local attractions.
The 2023-built, two-floor self-catering unit features a spacious open-plan loft area, a ground floor shower room, private patio, BBQ, parking, and sleeps up to four guests with a double bed and sofa bed, Smart TV with Netflix and a fully fitted kitchenette.
Cozy Modern Cottage Near Legoland, Windsor & Ascot - Maidenhead
9.9 163 reviews

Cozy Modern Cottage Near Legoland, Windsor & Ascot

house
This charming house is located in Holyport, just a short distance from the town centre and the River Thames, offering a peaceful setting for a relaxing getaway. The house is ideal for a family, with a private en-suite bedroom and a living room with a sofa bed that can accommodate two children.
The house has a fully equipped kitchen, a garden, and parking. Guests can enjoy the peaceful atmosphere, explore the nearby town centre, or take a stroll along the River Thames.

Best Maidenhead holiday rentals with parking

Food Lovers By Windsor And Heathrow With Secure Free Parking And Wifi - Maidenhead
8.8 5 reviews

Food Lovers By Windsor And Heathrow With Secure Free Parking And Wifi

apartment, Farnham Royal
This one-bedroom flat is located in Farnham Royal, offering free private parking and convenient access to local amenities.
This 50 square meter apartment provides a private entrance, free WiFi, a fully equipped kitchen, and accommodates up to seven guests.
Easy Airport Access - Heathrow Stay - Maidenhead
10 5 reviews

Easy Airport Access - Heathrow Stay

apartment, Farnham Royal
This recently renovated flat in Farnham Royal is situated 7.6 kilometres from Windsor Castle, 9.3 kilometres from Legoland Windsor, and 17.7 kilometres from London Heathrow Airport, offering convenient access to key attractions.
This apartment provides complimentary Wi-Fi, free on-site parking, and a fully equipped kitchen, comfortably accommodating up to three guests with a check-out time of 1 PM.
Entr - Modern Apartments In Windsor - Maidenhead
8.8 413 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.
Modern 2 Bed Ground Floor - Private Parking - By Tempstay - Maidenhead
9.0 5 reviews

Modern 2 Bed Ground Floor - Private Parking - By Tempstay

apartment, Windsor
This modern ground-floor flat in Windsor is situated 1.9km from Windsor Castle and 2.6km from Legoland Windsor, offering easy access to major attractions.
The 100 square metre property features two bedrooms, two bathrooms, and sleeps seven, boasting a fully equipped kitchen with a dishwasher and free Wi-Fi, plus free private parking.

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

Two Bed Apartment With Balcony Slough,windsor,legoland - Maidenhead
8.8 73 reviews

Two Bed Apartment With Balcony Slough,windsor,legoland

apartment, Slough
This two-bedroom flat is located in Slough, Berkshire, just 6 kilometres from Windsor Castle and 7.5 kilometres from Legoland Windsor. The property has received excellent user and cleanliness ratings, with a very good location rating.
The 70 square metre apartment has two bedrooms and one bathroom, comfortably accommodating up to three guests. Enjoy fresh air on the private balcony, stay connected with free Wi-Fi, and prepare meals in the fully equipped kitchen with an oven and microwave.
2bed 2bath Bliss, Private Parking - By Tempstay - Maidenhead
8.0 3 reviews

2bed 2bath Bliss, Private Parking - By Tempstay

apartment, Windsor
This Windsor apartment, located 1.6km from Windsor Castle and 2.6km from Legoland Windsor, offers easy access to major attractions.
The 175 square metre property features two bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, and a private balcony and garden, comfortably accommodating up to five guests.
Stylish 1br Flat | Central Windsor - Maidenhead
No reviews

Stylish 1br Flat | Central Windsor

apartment, Windsor
This Windsor city centre flat is conveniently located near King Edward Court Shopping Centre, the River Thames, and within 4.8km of Windsor Castle and LEGOLAND Windsor.
The 58 square metre self-catering apartment offers one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen with fridge, microwave, dishwasher and washing machine, plus a TV with DVD player and a sofa bed.
Newly Renovated Lovely Garden Driveway Parking - Pass The Keys - Maidenhead
9.7 3 reviews

Newly Renovated Lovely Garden Driveway Parking - Pass The Keys

house, Slough
This newly renovated three-bedroom house in Slough offers convenient access to attractions including Dorney Lake (6.1 kilometres), Cliveden House (6.3 kilometres), Windsor Castle (8.4 kilometres), and Legoland Windsor (9.9 kilometres).
This 111 square metre property accommodates up to nine guests, featuring a well-equipped kitchen with a dishwasher and microwave, a terrace, a garden, free Wi-Fi, and on-site parking.

Best Maidenhead holiday rentals with air conditioning

35 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests - Maidenhead
10 1 review

35 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests

apartment
This boutique flat is located in a quiet residential district of Great Britain, offering convenient access to Windsor (approximately 5 kilometers away), Heathrow Airport (approximately 7 kilometers away), and Central London.
This 35 square meter residence accommodates up to 5 guests, featuring one bedroom, a modern kitchen with a fridge and freezer, air conditioning, a private garden, and secure parking, with a flexible self check-in process.
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.
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.
30 M² Apartment ∙ 1 Bedroom ∙ 3 Guests - Maidenhead
No reviews

30 M² Apartment ∙ 1 Bedroom ∙ 3 Guests

apartment
This studio flat is located on Farnham Road, Slough, within easy walking distance of a bus stop, a supermarket, and Slough train station, with a metro station a 10-minute cycle away.
This 30 square meter studio offers a fully equipped kitchen, a sofa bed, a double bed, and free parking, accommodating up to three guests and situated near numerous restaurants, cafes, shops, and parks.
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