Holiday Rentals in Maidenhead

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Maidenhead holiday rentals
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304 Holiday Rentals and Airbnb in Maidenhead

Best family friendly Maidenhead holiday rentals

Among the 304 accommodations in Maidenhead, here are the 4 best family friendly rentals

Apartment ∙ 4 Bedrooms ∙ 8 Guests - Maidenhead
Maidenhead
28/07 – 04/08
NZ$555/nighttotal: NZ$3885 (7 )

Apartment ∙ 4 Bedrooms ∙ 8 Guests

4 6
apartment
This four-bedroom property is located in a quiet residential road within the Royal Borough of Windsor, offering a 20-minute walk to Windsor Castle and a 5-minute drive to LEGOLAND Windsor Resort.
This detached house accommodates up to 8 guests with a fully equipped kitchen, a private garden with seating, superfast WiFi, and offers discounts for weekly and monthly bookings.
Roseleigh Cottage In The Heart Of Cookham - Maidenhead
9.5 4 reviews
Maidenhead
17/10 – 24/10
NZ$407/nighttotal: NZ$2849 (7 )

Roseleigh Cottage In The Heart Of Cookham

1 4
house , Cookham
Roseleigh Cottage is a house located in Cookham, 3.9 kilometres from Cliveden House and 16.1 kilometres from Windsor Castle.
This accommodation offers Wi-Fi, a kitchen, and can host up to thirteen guests, making it a suitable base for exploring the area.
Castle Views| 2 Bed |Parking - Vat Q - By Tempstay - Maidenhead
Maidenhead
10/10 – 17/10
NZ$472/nighttotal: NZ$3304 (7 )

Castle Views| 2 Bed |Parking - Vat Q - By Tempstay

2 4
apartment , Berkshire
This Clewer East flat is ideally located within 3.2km of Windsor Castle, LEGOLAND Windsor, and the River Thames, offering easy access to major Berkshire attractions.
The two-bedroom, two-bathroom property sleeps four guests and boasts a fully equipped kitchen, including a dishwasher, a terrace, a garden, on-site parking, and free Wi-Fi; Windsor & Eton Central and Riverside stations are within walking distance.
Stable House - Eton Windsor - Maidenhead
9.5 226 reviews
Maidenhead
10/10 – 17/10
NZ$521/nighttotal: NZ$3647 (7 )

Stable House - Eton Windsor

2 4
house , Windsor
This charming house is located in Eton, Windsor, just 600 metres from Windsor Castle and a short drive from Dorney Lake and Legoland Windsor. The property has received excellent ratings for its location, cleanliness, and overall user experience.
The house has two bedrooms, accommodating up to four guests, and covers 64 square metres. It offers a fully equipped kitchen, a private garden, free Wi-Fi, and a tennis court, providing everything you need for a comfortable and enjoyable stay.

Best Maidenhead holiday rentals with parking

Ground Floorparkingwindsor Castle - By Tempstay - Maidenhead
8.0 1 review
Maidenhead
28/07 – 04/08
NZ$498/nighttotal: NZ$3486 (7 )

Ground Floorparkingwindsor Castle - By Tempstay

2 6
apartment , Berkshire
This family-friendly Windsor apartment in Clewer East, Berkshire, is an 11-minute walk from King Edward Court Shopping Centre and a 1.6km drive from Windsor Castle.
The two-bedroom, one-bathroom flat offers a private garden, terrace, parking, and amenities including Wi-Fi, a fully equipped kitchen, and proximity to LEGOLAND® Windsor, Thorpe Park, and Liquid Leisure.
Spacious 5-bedroom Home In Maidenhead - Maidenhead
Maidenhead
28/07 – 04/08
NZ$1366/nighttotal: NZ$9562 (7 )

Spacious 5-bedroom Home In Maidenhead

5 6
apartment , Maidenhead
This five-bedroom house in Maidenhead offers convenient access to the Thames River and is a short drive from LEGOLAND® Windsor and Thorpe Park.
This spacious 150 square meter property accommodates up to 10 guests with a modern kitchen, lounge, dining areas, a private garden, WiFi, and on-site parking.
A Lovely Three Bedroom House In Windsor - Maidenhead
8.3 43 reviews
Maidenhead
17/10 – 24/10
NZ$400/nighttotal: NZ$2800 (7 )

A Lovely Three Bedroom House In Windsor

3 4
house , Windsor
This three-bedroom house in Windsor is situated 2.4km from Legoland Windsor and 1.9km from Windsor Castle, offering easy access to these major attractions.
The 91 square metre property sleeps nine guests and boasts a fully equipped kitchen, private garden, free Wi-Fi, and on-site parking, along with a convenient mini-market.
Alder House Serviced Apt. Maidenhead By 360stays - Maidenhead
10 3 reviews
Maidenhead
16/07 – 23/07
NZ$410/nighttotal: NZ$2870 (7 )

Alder House Serviced Apt. Maidenhead By 360stays

1 1
apartment , Maidenhead
This two-bedroom Maidenhead apartment, near Stafferton Way, offers convenient access to Maidenhead town centre, the ODEON Luxe cinema, and Maidenhead United Football Club, all within a short driving distance (distances unspecified).
The self-catering flat sleeps up to six guests and includes free Wi-Fi, secure underground parking for two cars, a fully equipped kitchen with fridge, freezer and microwave, and amenities such as a Smart TV, Amazon Alexa, and a colour Wi-Fi printer; weekly linen and towel changes are provided, with mid-stay cleans available at an extra cost.

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.

Destinations nearby

Best Maidenhead holiday rentals with a balcony

Luxury 6-bed 6-bath Home Near Legoland With Parking - Maidenhead
10 1 review
Maidenhead
28/07 – 04/08
NZ$2119/nighttotal: NZ$14833 (7 )

Luxury 6-bed 6-bath Home Near Legoland With Parking

6 6
house , Windsor
This substantial 6-bedroom residence in Windsor is conveniently located just a 13-minute walk from LEGOLAND Windsor and 4 kilometres from Windsor Castle.
This family-friendly property offers 457 square metres of living space, accommodating up to 27 guests with 6 bathrooms, a well-equipped kitchen, a private garden with an outdoor dining area, and table tennis facilities, all complemented by free private parking and WiFi.
Central Windsor Gem | 1br Penthouse + Balcony - Maidenhead
8.4 5 reviews
Maidenhead
17/10 – 24/10
NZ$308/nighttotal: NZ$2156 (7 )

Central Windsor Gem | 1br Penthouse + Balcony

1 4
apartment , Windsor
This Windsor city centre flat is a short walk from King Edward Court Shopping Centre and the River Thames, and within 4.8 kilometres of Windsor Castle and LEGOLAND Windsor.
The 59-square-metre apartment sleeps four, featuring a fully equipped kitchen with dishwasher, a washing machine, a TV and DVD player, and a sofa bed; enjoy proximity to Windsor & Eton Central and Riverside train stations.
Pass The Keys Modern Townhouse With Garden And Parking In Ascot - Maidenhead
Maidenhead
21/06 – 29/06
NZ$481/nighttotal: NZ$3848 (8 )

Pass The Keys Modern Townhouse With Garden And Parking In Ascot

3 4
house , Ascot
This modern three-bedroom townhouse in Ascot is conveniently located 1.8km from LaplandUK, 7.9km from Legoland Windsor, and 11.3km from Windsor Castle.
The 111 square metre property boasts three bathrooms, a private garden with terrace, parking, and sleeps up to 10 guests, offering free Wi-Fi and a fully equipped kitchen including a dishwasher.
Family Home, View Of Windsor Castle - Maidenhead
8.8 48 reviews
Maidenhead
17/10 – 24/10
NZ$392/nighttotal: NZ$2744 (7 )

Family Home, View Of Windsor Castle

3 4
house , Dorney
This family home in Dorney, Berkshire, is situated 4.3km from Dorney Lake and 7.2km from Windsor Castle, offering easy access to these popular attractions.
The 95 square metre property sleeps up to 10 guests in 3 bedrooms and 2 bathrooms, and boasts a garden with terrace, free Wi-Fi, free parking, and free bicycle use for exploring the area.

Best Maidenhead holiday rentals with air conditioning

3 Bed For 8 Apartment In The Centre Of Slough - Maidenhead
Maidenhead
10/08 – 20/08
NZ$423/nighttotal: NZ$4230 (10 )

3 Bed For 8 Apartment In The Centre Of Slough

3 1
apartment , Slough
This Slough apartment, less than 1.6km from Slough Ice Arena and the River Thames, and just over 3.2km from Windsor Castle, offers convenient access to Slough railway station (a 15-minute walk).
The three-bedroom flat sleeps eight, includes a fully equipped kitchen, washing machine, hairdryer, iron and ironing board, and benefits from on-site parking and air conditioning.
Period Luxury Converted Barn Windsor/maidenhead - Perfect For Family Groups - Maidenhead
9.3 3 reviews
Maidenhead
17/10 – 24/10
NZ$4979/nighttotal: NZ$34853 (7 )

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

9 4
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.
3-bed Home, Free Parking, Smart Tv,family & Business Ready - Maidenhead
Maidenhead
17/10 – 24/10
NZ$539/nighttotal: NZ$3773 (7 )

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

3 4
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.
Willow Court Farm Studio South & Petting Farm, 8 Mins From Legoland & Windsor, 15 Mins From Lapland Uk - Maidenhead
9.7 99 reviews
Maidenhead
17/10 – 24/10
NZ$591/nighttotal: NZ$4137 (7 )

Willow Court Farm Studio South & Petting Farm, 8 Mins From Legoland & Windsor, 15 Mins From Lapland Uk

1 4
studio , Windsor
Willow Court Farm Studio South & Petting Farm is located just 8km from Legoland and 15km from Lapland UK, offering a peaceful rural retreat close to Windsor's popular attractions. The self-catering unit has consistently received excellent ratings for cleanliness, location and overall experience.
The studio, measuring 33 square metres, comfortably accommodates two guests in a single bedroom with a private bathroom. Guests can enjoy modern amenities including a well-equipped kitchen, a private terrace, a garden, free parking and Wi-Fi, as well as a unique petting farm experience on-site.
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