Holiday Rentals in Maidenhead

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Maidenhead holiday rentals
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Best Holiday rentals and Airbnb offers in Maidenhead

Discover Family-Friendly Self-Catering Rentals in Maidenhead

Family holidays in Maidenhead work best when your holiday rental is properly set up with space and city attractions within easy reach.

Cozy 3br Retreat In Prime Location - Maidenhead
Maidenhead
16/07 – 23/07
£217/nighttotal: £1519 (7 )

Cozy 3br Retreat In Prime Location

3 1
house , Slough
This 3-bedroom house in Slough is situated 5.8 kilometres from Dorney Lake and 6.4 kilometres from Brunel University, offering convenient access to Windsor Castle (5.8 kilometres) and Legoland Windsor (8.2 kilometres).
This family-friendly property accommodates up to 13 guests with 3 bedrooms, 1 bathroom, and includes free WiFi and private parking, alongside a kitchen equipped with a microwave and dishwasher.
Discover Heaven's Way Heathrow: 25% Off! Near Windsor Castle, Legoland, Windsor! - Maidenhead
Maidenhead
28/07 – 04/08
£307/nighttotal: £2149 (7 )

Discover Heaven's Way Heathrow: 25% Off! Near Windsor Castle, Legoland, Windsor!

4 6
apartment , Slough
This Slough family home, near Dorney Court (under 5km) and within 10km of Windsor Castle and Cliveden House, offers convenient access to Burnham and Taplow railway stations.
Sleeping nine guests, this four-bedroom, two-bathroom property boasts a fully equipped kitchen, in-house laundry, a Smart TV, and on-site parking, plus a children's playground.
Bright & Spacious 3-bed, 2-bath Home In Graylands Close - Maidenhead
10 1 review
Maidenhead
21/06 – 29/06
£207/nighttotal: £1656 (8 )

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

3 4
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.
Cheerful Modern Apt Central Maidenhead, Parking - Maidenhead
9.9 230 reviews
Maidenhead
17/10 – 24/10
£152/nighttotal: £1064 (7 )

Cheerful Modern Apt Central Maidenhead, Parking

1 4
apartment , Berkshire
This one-bedroom flat is located in Maidenhead, a Thames riverside town, just 700 metres from the town centre and railway station. It has received excellent ratings for location, cleanliness, and overall user experience.
The flat offers a comfortable and private stay for up to two guests, with a double bedroom, a large bathroom, a cosy sitting room with a sofa bed and en-suite shower room, and a well-equipped kitchenette. It includes modern amenities such as a fridge, microwave, induction hob, and kettle, along with pots, pans, utensils, crockery, and cutlery.

Compare Holiday Rentals with Parking in Maidenhead

Free on-site parking comes with these holiday rentals in Maidenhead, allowing you to focus on the city centre from day one.

3 Bed In Bray (Oc-s32608) - Maidenhead
Maidenhead
28/07 – 04/08
£1357/nighttotal: £9499 (7 )

3 Bed In Bray (Oc-s32608)

3 6
cottage , Bray
This waterside property in Maidenhead is located 500 metres from the River Thames and a 7-minute drive from Bray Marina.
This 3-bedroom house for 6 guests offers Wi-Fi, a dishwasher, and is a 7-minute drive from LEGOLAND® Windsor and Thorpe Park.
Modern 2 Bed Oasis -Parking & Garden - By Tempstay - Maidenhead
Maidenhead
21/06 – 29/06
£201/nighttotal: £1608 (8 )

Modern 2 Bed Oasis -Parking & Garden - By Tempstay

2 4
apartment , Berkshire
This Clewer North apartment, situated less than 3.2km from Windsor Castle and LEGOLAND Windsor, offers easy access to the Thames Path and King Edward Court Shopping Centre.
The two-bedroom, two-bathroom flat sleeps four, includes a fully equipped kitchen with dishwasher and in-unit laundry, plus a private garden and parking; nearby Windsor & Eton Central and Riverside train stations provide convenient transport links.
Windsor Mews By Stay Focused Sa - Maidenhead
9.4 145 reviews
Maidenhead
10/10 – 17/10
£209/nighttotal: £1463 (7 )

Windsor Mews By Stay Focused Sa

2 4
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.
Modern Room & Bath In Maidenhead Near Heathrow Airport - Maidenhead
Maidenhead
16/07 – 23/07
£86/nighttotal: £602 (7 )

Modern Room & Bath In Maidenhead Near Heathrow Airport

1 1
apartment , Taplow
This modern one-bedroom apartment in Taplow offers a convenient location, approximately 6.4km from Maidenhead train station providing easy access to London, and within 24km of LEGOLAND Windsor and 32km from Heathrow Airport.
The self-catering flat features a double room with ensuite bathroom, microwave, dishwasher, air conditioning, parking, and accommodates two guests, benefiting from a weekly cleaning service and discounts for longer stays.

Frequently asked questions about holiday rentals in Maidenhead

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

    Maidenhead is great for families. The Maidenhead Aquatics and Leisure Centre is a popular choice with a swimming pool and leisure facilities. For outdoor fun, the Braywick Park and the National Trust's Cliveden are both great options.
  • 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, when the weather is pleasant and the prices are generally lower.
  • What are the most popular Airbnbs in Maidenhead?

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

    Maidenhead hosts several events throughout the year, including the Maidenhead River Festival in June, which features live music, boat races, and a funfair. The nearby Windsor Castle also hosts various events, such as the Royal Windsor Horse Show in May.
  • 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?

    Maidenhead offers plenty of budget-friendly activities. You can enjoy a free walk along the Thames Path, visit the free Maidenhead Library, or explore the local parks like Braywick Park.
  • What are the best rentals for families and kids in Maidenhead?

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

    For a taste of local cuisine, try The Old House at Boston Manor for traditional pub grub, or the award-winning The Fat Duck, known for its innovative and experimental gastronomy.
  • What are the best rentals or Airbnbs with a jacuzzi in Maidenhead?

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

    The Thames Path offers a scenic walk or cycle along the River Thames, while the Maidenhead to Marlow towpath is a popular choice for a leisurely bike ride.
  • Are there pet-friendly attractions in Maidenhead?

    Yes, many attractions in Maidenhead are pet-friendly. Braywick Park is great for dog walks, and many pubs and restaurants welcome dogs on their terraces.
  • What are the benefits of choosing a vacation rental in Maidenhead?

    Vacation rentals offer more space and privacy than hotels, and often come with amenities like kitchens and laundry facilities. They can also be a more cost-effective option, especially for families or groups.
  • What are the top sports attractions and facilities in Maidenhead?

    Maidenhead boasts a variety of sporting facilities. The Maidenhead Rugby Club is a popular spot for rugby fans, and the Maidenhead Aquatics and Leisure Centre offers a range of swimming and fitness activities.

Destinations nearby

Check Out Holiday Rentals with a Balcony in Maidenhead

Choosing a holiday rental in Maidenhead with a private balcony offers city skyline views that are worth every penny. Compare options and find yours.

Relaxing Central Windsor Getaway For Families - By Tempstay - Maidenhead
9.7 4 reviews
Maidenhead
28/07 – 04/08
£329/nighttotal: £2303 (7 )

Relaxing Central Windsor Getaway For Families - By Tempstay

3 6
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).
1 Bed With Balcony In Maidenhead By Elizabeth Line - Maidenhead
Maidenhead
10/08 – 20/08
£145/nighttotal: £1450 (10 )

1 Bed With Balcony In Maidenhead By Elizabeth Line

1 1
apartment , Berkshire
This one-bedroom flat is situated on Maidenhead High Street, a 5-minute walk from Maidenhead Station, offering excellent access to London Paddington and Heathrow, with the River Thames and the culinary village of Bray within easy reach.
This 4 square meter apartment accommodates two guests and features a private balcony overlooking the High Street, a kitchen with a fridge and dishwasher, and is professionally cleaned with hotel-quality linen provided.
Your Place In Windsor With Kitchen And Terrace - Maidenhead
9.5 2 reviews
Maidenhead
10/10 – 17/10
£128/nighttotal: £896 (7 )

Your Place In Windsor With Kitchen And Terrace

1 4
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.
Radiant Retreat Ideal For Legoland, Windsor, & Lhr - Maidenhead
9.7 57 reviews
Maidenhead
17/10 – 24/10
£220/nighttotal: £1540 (7 )

Radiant Retreat Ideal For Legoland, Windsor, & Lhr

3 4
house , Slough
This recently renovated Slough holiday home is situated 6.4km from Windsor Castle, 7km from Dorney Lake, and 16km from London Heathrow Airport, offering easy access to major attractions.
The 109 square metre property boasts three bedrooms, two bathrooms, and sleeps up to ten guests, featuring a fully equipped kitchen, free Wi-Fi, private parking, and an outdoor dining area.

Best Maidenhead holiday rentals with air conditioning

35 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests - Maidenhead
10 1 review
Maidenhead
17/10 – 24/10
£158/nighttotal: £1106 (7 )

35 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests

1 4
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.
House Sleeps 10 With Parking And Garden - Maidenhead
Maidenhead
10/10 – 17/10
£269/nighttotal: £1883 (7 )

House Sleeps 10 With Parking And Garden

4 4
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.
Radiant Penthouse On The Banks Of The Thames - Pass The Keys - Maidenhead
9.8 150 reviews
Maidenhead
10/10 – 17/10
£325/nighttotal: £2275 (7 )

Radiant Penthouse On The Banks Of The Thames - Pass The Keys

3 4
apartment , Windsor
This penthouse apartment is located on Windsor Riverside, just a short walk from Windsor Castle and the town centre, making it a great base for exploring the area. The apartment has excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This spacious 3-bedroom apartment can accommodate up to 7 guests, with a floor area of 93 square metres. The apartment comes equipped with a fully equipped kitchen, free Wi-Fi, parking, a washing machine, and a garden, ensuring a comfortable and convenient stay.
Cosy Family Home Near Thorpe Park & Legoland - Maidenhead
8.3 12 reviews
Maidenhead
10/10 – 17/10
£319/nighttotal: £2233 (7 )

Cosy Family Home Near Thorpe Park & Legoland

4 4
house , Old Windsor
This charming house is located in Old Windsor, just a short drive from Windsor Castle, Thorpe Park, and Legoland Windsor, making it a perfect base for exploring the area. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The home offers four bedrooms, comfortably accommodating up to seven guests, and features a fully equipped kitchen with a dishwasher, a private garden, free Wi-Fi, and parking. Enjoy the convenience of being close to the River Thames and the beautiful surrounding countryside, as well as easy access to Heathrow Airport.
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