Holiday Rentals in Maidenhead

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Maidenhead holiday rentals
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445 Holiday Rentals and Airbnb in Maidenhead

Best family friendly Maidenhead holiday rentals

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

Hope Cottage In Slough With Parking - Maidenhead
9.6 5 reviews

Hope Cottage In Slough With Parking

house, Slough
Hope Cottage, a two-bedroom house in Slough, is situated approximately 4.8 kilometres from Windsor Castle and 6.6 kilometres from Legoland Windsor.
This 62 square metre self-catering property sleeps nine guests and offers free Wi-Fi, private parking, a garden, and a fully equipped kitchen.
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.
Compact 2-bed Flat With Ev Parking / Charge And Ac - Maidenhead
9.4 88 reviews

Compact 2-bed Flat With Ev Parking / Charge And Ac

apartment
This Windsor duplex apartment offers excellent location, a short walk from Windsor Racecourse and the town centre, providing easy access to Berkshire's countryside.
Sleeping up to 10 guests, this premium three-bathroom property boasts a well-equipped kitchen, spacious living area with flat-screen TV and broadband, and two double bedrooms with hotel-quality linen; free parking and an EV charger are also available.
Garfield Place Cosy 2-bedroom Cottage Central Windsor With Parking - Maidenhead
9.4 69 reviews

Garfield Place Cosy 2-bedroom Cottage Central Windsor With Parking

apartment, Windsor
This two-bedroom apartment is located in central Windsor, just 500 metres from Windsor Castle and a 3 km drive from Legoland Windsor. The apartment has received excellent ratings for location, cleanliness and overall user experience.
The apartment is 61 square metres and features a fully equipped kitchen with a fridge, freezer, microwave oven and dishwasher. Guests can enjoy a range of amenities including a swimming pool, terrace, garden, tennis court and parking.

Best Maidenhead holiday rentals with 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.
Modern 2 Bed Apartment - Allocated Parking - By Tempstay - Maidenhead
9.2 6 reviews

Modern 2 Bed Apartment - Allocated Parking - By Tempstay

apartment, Windsor
This modern Windsor apartment, a short 1.8km from Windsor Castle and 2.6km from Legoland Windsor, offers convenient access to major attractions.
The 100 square metre property boasts two bedrooms, two bathrooms, a fully equipped kitchen including a dishwasher, and private parking, comfortably accommodating up to five guests with access to a balcony and garden.
Stylish Windsor Getaway W Balcony - Free Parking - By Tempstay - Maidenhead
8.5 19 reviews

Stylish Windsor Getaway W Balcony - Free Parking - By Tempstay

apartment, Windsor
This stylish flat is located just 1.9 kilometres from Windsor Castle and 2.6 kilometres from Legoland Windsor, making it ideal for exploring these popular attractions. The apartment has received very good user ratings for its location, cleanliness, and overall experience.
The 120 square metre apartment comfortably accommodates up to four guests in its two bedrooms and two bathrooms. The flat comes with a fully equipped kitchen, private parking, and a balcony, perfect for enjoying a relaxing evening in Windsor.
Windsor Mews By Stay Focused Sa - Maidenhead
9.4 151 reviews

Windsor Mews By Stay Focused Sa

house, Windsor
Windsor Mews by Stay Focused SA is a recently renovated holiday home located just 2.1km from Legoland Windsor and within easy reach of other attractions like Windsor Castle, LaplandUK, and Dorney Lake. The property has received excellent ratings for cleanliness, location, and user experience.
The two-bedroom house can accommodate up to six guests and is fully equipped with a kitchen, washing machine, and free Wi-Fi. Guests can enjoy a comfortable stay with towels and bed linen provided, and the house offers a private entrance for added privacy.

Frequently asked questions about holiday rentals in Maidenhead

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

    The Maidenhead Heritage Centre is a great place to learn about the town's history, and the Maidenhead Aquatics and Leisure Centre has a swimming pool and other activities for kids. For a day out, Legoland Windsor is only a short drive away.
  • What are the best Airbnb and holiday rentals 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, as you'll likely get better deals and less crowds. The summer months are popular with families, so book in advance.
  • What are the most popular Airbnbs in Maidenhead?

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

    The Maidenhead River Festival is a popular event in June with live music, boat races, and food stalls. The Maidenhead Food Festival in September is another great option, showcasing local produce and cuisine.
  • What are the best holiday rentals with a pool in Maidenhead?

    Spacious Sunny Apartment, Sheephouse Manor and Modern Bungalow With Private Swimming Pool are the best holiday rentals with a pool in Maidenhead.

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

    A walk along the towpath of the River Thames is a great free activity. The Maidenhead Library is also free to visit and offers a variety of events and activities.
  • What are the best rentals for families and kids in Maidenhead?

  • What are the best restaurants with local dishes in Maidenhead?

    The Maidenhead Fish Bar is a local favourite for traditional fish and chips. For a more upscale dining experience, try The Maidenhead Inn, which serves classic British cuisine.
  • What are the best rentals or Airbnbs with a jacuzzi in Maidenhead?

  • What are the best walking or cycling routes in Maidenhead?

    The Maidenhead to Marlow towpath walk is a lovely 10km route along the River Thames. For cyclists, the Maidenhead to Windsor cycle route is a popular choice, offering scenic views and a mix of flat and hilly terrain.
  • Are there pet-friendly attractions in Maidenhead?

    The Maidenhead Thicket is a great place to walk your dog, and many pubs and restaurants in the town centre are dog-friendly.
  • What are the benefits of choosing a vacation rental in Maidenhead?

    Vacation rentals offer more space and privacy than a hotel, and often come with amenities like a kitchen, which allows you to save money on dining out. They can also be a great option for families or groups.
  • What are the top sports attractions and facilities in Maidenhead?

    The Maidenhead Aquatics and Leisure Centre is a popular spot for swimming, fitness classes, and other activities. The Maidenhead Rugby Club is also a popular destination for sports fans.

Popular destinations

Best Maidenhead holiday rentals with a balcony

Eiffel's Secret Garden - Maidenhead
No reviews

Eiffel's Secret Garden

apartment, High Wycombe
Eiffel's Secret Garden, a one-bedroom flat in High Wycombe, offers tranquil garden views and is located 10.5 kilometres from Cliveden House and 19.3 kilometres from Dorney Lake, with easy access to Uxbridge Tube Station (20.9 km) for London travel.
This non-smoking apartment features a fully equipped kitchen, a terrace for outdoor relaxation, and can accommodate up to 15 guests, making it ideal for exploring nearby attractions like Windsor Castle (22.5 km) and Legoland Windsor (24.1 km).
Hampden Apartments - The Anne - Maidenhead
9.0 190 reviews

Hampden Apartments - The Anne

apartment, Windsor
The Hampden Apartments - The Anne is located just 1.9km from Windsor Castle, making it ideal for exploring this historic town. The apartment has excellent ratings for location, cleanliness, and user experience.
This one-bedroom flat offers 70 square metres of space, comfortably accommodating up to four guests. Enjoy a fully equipped kitchen, a private balcony with city views, free Wi-Fi, and parking, perfect for a relaxing and convenient stay.
1br Apt Near Heathrow By Tempstay - Maidenhead
9.2 30 reviews

1br Apt Near Heathrow By Tempstay

apartment, Slough
This one-bedroom flat is conveniently located in Slough, just 6 kilometres from Windsor Castle and 7 kilometres from Legoland Windsor, making it an ideal base for exploring the area. The property has received consistently high ratings for its location, cleanliness and overall quality.
The flat is 50 square metres in size and comfortably accommodates two guests. It offers a fully equipped kitchen with a fridge and dishwasher, a private balcony, a garden, and free Wi-Fi.
1br Gem, Private Parking - Vat Q - By Tempstay - Maidenhead
10 1 review

1br Gem, Private Parking - Vat Q - By Tempstay

apartment, Berkshire
This Clewer East flat is ideally located within 2km of King Edward Court Shopping Centre and the River Thames, and within 3km of Windsor Castle and LEGOLAND Windsor.
The one-bedroom, one-bathroom apartment sleeps two guests and offers a fully equipped kitchen with dishwasher, in-unit laundry, and access to a relaxing garden; nearby attractions include Windsor & Eton Central and Riverside train stations (22 and 27 minutes' walk respectively).

Best Maidenhead holiday rentals with air conditioning

Warwick Road Studios - Maidenhead
9.0 194 reviews

Warwick Road Studios

apartment, Beaconsfield
Warwick Road Studios is located in Beaconsfield, just under 9km from Cliveden House and 16km from Uxbridge, offering a peaceful retreat within easy reach of both historic attractions and bustling town life. The apartment has received very good user ratings and excellent ratings for its location and cleanliness.
This one-bedroom, one-bathroom flat offers a comfortable and convenient base for exploring Beaconsfield. It comes equipped with a kitchen featuring a fridge, microwave, and dishwasher, as well as air conditioning and free Wi-Fi for added comfort and convenience.
Period Luxury Converted Barn Windsor/maidenhead - Perfect For Family Groups - Maidenhead
9.5 4 reviews

Period Luxury Converted Barn Windsor/maidenhead - Perfect For Family Groups

house, Taplow
This period luxury converted barn is located in Taplow, Berkshire, just 3 kilometres from Dorney Lake and 8 kilometres from Cliveden House.
The spacious villa features 8 bedrooms, 7 bathrooms, and a private pool and hot tub, making it ideal for large families or groups, with a total floor area of 551 square metres.
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.
Stylish Compact 1-bed Flat + Parking + Ac + Garden - Maidenhead
9.1 64 reviews

Stylish Compact 1-bed Flat + Parking + Ac + Garden

apartment
This ground-floor flat is situated near Windsor, a short walk from Windsor Racecourse and the town centre, offering easy access to Berkshire's countryside.
The one-bedroom apartment sleeps two guests and features a modern kitchen with a dishwasher and Nespresso machine, a king-size bed with blackout blinds, free off-street parking, and speedy broadband; professional cleaning and contactless self check-in are also provided.
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