Best Holiday rentals and Airbnb offers in Maidenhead
Maidenhead
10/08 – 20/08
SG$221/nighttotal: SG$2210 (10 )
The Green Views For Contractors, Family/couples, Tourists
1 1
apartment , Maidenhead
This Maidenhead apartment, located in a peaceful residential area with convenient access to Nirvana Spa, LEGOLAND Windsor (distances to be verified), and other attractions, offers a tranquil retreat. The one-bedroom flat sleeps three, features a fully equipped kitchen including a dishwasher, a private entrance, complimentary parking, and is ideal for couples or solo travellers seeking a relaxing stay near Maidenhead's leisure activities.
9.9 70 reviews
Maidenhead
10/08 – 20/08
SG$217/nighttotal: SG$2170 (10 )
Limited Conversational French Language
1 1
apartment , Berkshire
This one-bedroom Berkshire apartment, ideally located near Bray, offers easy access to London via the Elizabeth Line and GWR trains, and is approximately 8km from Windsor Castle and Legoland Windsor. The self-catering flat sleeps two guests and includes a kitchen with fridge, freezer, and dishwasher, a garden, parking, and excellent internet access; explore the nearby Thames Path and Berkshire countryside.
9.9 201 reviews
Maidenhead
10/10 – 17/10
SG$269/nighttotal: SG$1883 (7 )
Luxurious Barn Between Marlow & Henley
1 4
apartment , Royaume-Uni
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.
Maidenhead
10/08 – 20/08
SG$249/nighttotal: SG$2490 (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.
8.3 8 reviews
Maidenhead
21/06 – 29/06
SG$355/nighttotal: SG$2840 (8 )
2 Bedroom Apt.02 With Parking In Maidenhead
1 4
apartment , Berkshire
This Maidenhead apartment, a 4-minute walk (0.64 km) from Maidenhead train station, offers easy access to Central London and other Berkshire destinations. The 75m² two-bedroom, two-bathroom flat sleeps four, features a fully equipped kitchen with freezer and microwave, free gated parking, a Smart TV, and 24/7 guest support.
8.0 2 reviews
Maidenhead
28/07 – 04/08
SG$425/nighttotal: SG$2975 (7 )
Maidenhead - Stunning, Spacious - Three Bedrooms (
3 6
apartment , Berkshire
This three-bedroom penthouse apartment in Maidenhead, Berkshire, offers easy access to Berkshire's attractions and is ideally located for exploring the county. The spacious property sleeps five guests, boasts a large open-plan kitchen, living area, and private balcony, plus allocated underground parking and a communal roof terrace, making it perfect for families or groups.
8.7 398 reviews
Maidenhead
17/10 – 24/10
SG$399/nighttotal: SG$2793 (7 )
Central Windsor Apartment Facing The Castle
2 4
apartment , Windsor
This centrally located Windsor flat is just a 4.2km walk from Windsor Castle and a short stroll from the town centre, offering easy access to shops, restaurants and attractions. The apartment has received very good user, location and cleanliness ratings. The two-bedroom flat is spacious and comfortable, perfect for families or groups of friends. It comes with a fully equipped kitchen, washing machine, free Wi-Fi, a private entrance, and a Jacuzzi, making it perfect for a relaxing and enjoyable stay.
9.3 6 reviews
Maidenhead
21/06 – 29/06
SG$259/nighttotal: SG$2072 (8 )
2 Bed 2 Bath W/ Parking Windsor / 20pv
1 4
apartment , Berkshire
This Windsor apartment, less than 1.6km from Windsor town centre, offers easy access to Windsor Castle and other Berkshire attractions. The two-bedroom, two-bathroom flat sleeps four, features a fully equipped kitchen with dishwasher and washer-dryer, secure parking, and central heating.
9.2 27 reviews
Maidenhead
10/08 – 20/08
SG$231/nighttotal: SG$2310 (10 )
1br Apt Near Heathrow By Tempstay
1 1
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.
9.5 12 reviews
Maidenhead
10/10 – 17/10
SG$268/nighttotal: SG$1876 (7 )
Very Pretty 2 Br Cottage On Edge Of National Trust
2 4
apartment , Royaume-Uni
This recently refurbished Victorian terraced cottage is located in a semi-rural setting next to National Trust lands, a few hundred meters from a gastro pub and cricket pitch, and a short drive from Marlow and Maidenhead town centres. This two-bedroom cottage accommodates up to four guests and features an open-plan living space with a fireplace, a fully fitted kitchen, a luxury bathroom with underfloor heating, and secluded south-facing gardens with a patio and lawn, offering excellent opportunities for walking and cycling on Pinkneys Green common.
9.3 55 reviews
Maidenhead
17/10 – 24/10
SG$235/nighttotal: SG$1645 (7 )
Electric Escape 1br With Ev Point And Free Parking
1 4
apartment , Windsor
This Windsor apartment, a 48-square-metre (517 sq ft) one-bedroom flat, boasts a prime location just 0.4 km from Windsor Castle and Windsor town centre, offering easy access to Legoland Windsor and other attractions. The self-catering property sleeps up to nine guests and includes a fully equipped kitchen with a dishwasher, free Wi-Fi, and private entrance; towels, bed linen, and a hairdryer are provided.
9.6 14 reviews
Maidenhead
28/07 – 04/08
SG$396/nighttotal: SG$2772 (7 )
Great 4 Bed House & Parking - Great For Contactors
4 6
apartment , Berkshire
This four-bedroom house in Holyport, Berkshire, offers easy access to the M4 motorway, Windsor Castle (16-32km), Legoland Windsor (16-32km), and the River Thames, all within a 16-32km radius. The property sleeps eight, features a kitchen with a fridge and microwave, parking, internet access, and is available for short, medium, or long-term lets, ideal for contractors or families visiting Berkshire.
Best family friendly Maidenhead holiday rentals
Among the 304 accommodations in Maidenhead, here are the 4 best family friendly rentals
8.2 107 reviews
Maidenhead
28/07 – 04/08
SG$1017/nighttotal: SG$7119 (7 )
Rural 7 And 2 Bed Lodge Stays In Windsor! Hot Tub! Sleeps 20
7 6
house , Bray
This lodge is located in Bray, just 5.5 kilometres from Windsor Castle and 5.8 kilometres from Legoland Windsor, making it a great base for exploring the area. The property has received very good user ratings and excellent location and cleanliness ratings. This spacious house comfortably sleeps 20 people, making it ideal for large families or groups of friends. It offers a fully equipped kitchen, modern amenities, a garden with outdoor play equipment, a hot tub, and a terrace or balcony, providing everything you need for a comfortable and enjoyable stay.
9.3 240 reviews
Maidenhead
10/10 – 17/10
SG$277/nighttotal: SG$1939 (7 )
Hampden Apartments - The Diana
1 4
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.
Maidenhead
17/10 – 24/10
SG$233/nighttotal: SG$1631 (7 )
Anna’s Stylish House - Near Legoland
3 4
house , Windsor
This family-friendly detached house in Windsor is situated 2.6 kilometres from Windsor Castle, with Legoland Windsor just 3.2 kilometres away, offering convenient access to local attractions. This 80 square metre property accommodates up to nine guests across three bedrooms and features a fully equipped kitchen, complimentary WiFi, a private garden, and off-street parking.
9.4 122 reviews
Maidenhead
10/10 – 17/10
SG$267/nighttotal: SG$1869 (7 )
4 The Courtyard Central Windsor 2br
2 4
apartment , Windsor
This 2-bedroom apartment is conveniently located in central Windsor, just 400 metres from Windsor Castle and a short walk from the town centre, offering easy access to all the attractions and amenities. It has received excellent ratings for location, cleanliness and overall user experience. The flat features a fully equipped kitchen and a washing machine, making it ideal for longer stays. Guests can enjoy free private parking, a tennis court, and free Wi-Fi, as well as being within easy reach of Legoland Windsor, LaplandUK, Dorney Lake and Thorpe Park.
Best Maidenhead holiday rentals with parking
8.9 196 reviews
Maidenhead
17/10 – 24/10
SG$283/nighttotal: SG$1981 (7 )
Victorian Convent
2 4
apartment , Windsor
This apartment is located in Windsor, just 1.6km from Windsor Castle and 2.4km from Legoland Windsor, offering a convenient base for exploring the town's attractions. It's situated in a historic Victorian convent, adding a unique charm to your stay. The apartment has consistently received excellent ratings for location, cleanliness, and user experience, ensuring a comfortable and enjoyable stay. The 93 square metre apartment has two bedrooms and two bathrooms, comfortably accommodating up to four guests. It features a modern kitchen with a dishwasher and oven, a relaxing garden, free parking, and free Wi-Fi, providing everything you need for a relaxing and enjoyable stay.
10 5 reviews
Maidenhead
10/08 – 20/08
SG$130/nighttotal: SG$1300 (10 )
Easy Airport Access - Heathrow Stay
1 1
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.
Maidenhead
21/06 – 29/06
SG$346/nighttotal: SG$2768 (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.
Maidenhead
28/07 – 04/08
SG$771/nighttotal: SG$5397 (7 )
Spacious Family Home Near Windsor - By Tempstay
3 6
apartment , Berkshire
This three-bedroom Windsor apartment in Clewer North offers stunning river views, a short walk from Windsor Castle and Windsor town centre, and a 5-minute (8 km) drive from LEGOLAND. The self-catering property sleeps six (four adults and two children), boasts a spacious open-plan kitchen-diner, three bathrooms (one ensuite), private parking for two cars, and a garden, making it ideal for families visiting Berkshire.
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 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.
Destinations nearby
Best Maidenhead holiday rentals with a balcony
8.8 109 reviews
Maidenhead
17/10 – 24/10
SG$428/nighttotal: SG$2996 (7 )
Stylish Home With Free Parking - 10 Mins To Legoland! - By Tempstay
4 4
apartment , Windsor
This apartment is situated in Windsor, just a short distance from Legoland Windsor, Windsor Castle, and other attractions. The area is well-connected and offers a pleasant environment for families and groups. The apartment has consistently received excellent ratings for its cleanliness, location, and overall experience. This spacious four-bedroom dwelling is perfect for larger groups. It includes a fully equipped kitchen, a private garden, free Wi-Fi, parking, and a washing machine, making it ideal for comfortable and convenient stays.
9.5 19 reviews
Maidenhead
17/10 – 24/10
SG$347/nighttotal: SG$2429 (7 )
Parkview Apartments Windsor
1 4
apartment , Windsor
Parkview Apartments Windsor is conveniently located just a short distance from both Legoland Windsor and Windsor Castle, making it an ideal base for exploring the town's attractions. The apartment receives excellent ratings for location, cleanliness, and overall user experience. This one-bedroom flat comfortably accommodates up to four guests and offers a spacious 25 square metres of living space. The apartment is fully equipped with a kitchen, washing machine, and a balcony, perfect for enjoying the fresh air and views.
Maidenhead
17/10 – 24/10
SG$242/nighttotal: SG$1694 (7 )
Newly Renovated Lovely Garden Driveway Parking - Pass The Keys
3 4
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.
Maidenhead
10/10 – 17/10
SG$319/nighttotal: SG$2233 (7 )
2-bdr- Balcony- Parking-walk To Castle By Tempstay
2 4
apartment , Windsor
This two-bedroom flat in Windsor boasts a prime city centre location, situated a 15-minute walk from Windsor Royal Shopping Centre and an 11-minute walk from King Edward Court Shopping Centre, with Windsor Castle also within easy reach. This apartment accommodates up to four guests and features a well-equipped kitchen, complimentary Wi-Fi, on-site parking, and an in-unit washer and dryer, offering convenience for stays near LEGOLAND® Windsor and Thorpe Park.
Best Maidenhead holiday rentals with air conditioning
10 1 review
Maidenhead
28/07 – 04/08
SG$579/nighttotal: SG$4053 (7 )
Modern 4br Family Home | Private Driveway
4 6
apartment , Berkshire
This spacious four-bedroom flat is located in Maidenhead, Berkshire, offering convenient access to local amenities and a prime position for exploring the area. This property accommodates up to eight guests with two bathrooms, a fully equipped kitchen featuring a fridge, freezer, microwave, and dishwasher, air conditioning, free Wi-Fi, a garden, and on-site parking.
8.8 81 reviews
Maidenhead
10/08 – 20/08
SG$696/nighttotal: SG$6960 (10 )
Castle Properties: The Sovereign 5 Bed Town House
5 1
apartment , Windsor
This 5-bedroom townhouse is located just a short walk from Windsor Castle and a few hundred yards from the town centre, offering easy access to shops, restaurants and attractions. The property has received very good user ratings, an excellent location rating and a very good cleanliness rating. The property is 200 square metres in size and has a fully equipped kitchen with a dishwasher and kettle, as well as two bathrooms with a bath and hairdryer. Guests can enjoy a private entrance, a welcome basket, free WiFi, air conditioning, parking and a restaurant on site.
10 1 review
Maidenhead
17/10 – 24/10
SG$273/nighttotal: SG$1911 (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.
9.1 214 reviews
Maidenhead
21/06 – 29/06
SG$475/nighttotal: SG$3800 (8 )
Warwick Road Studios
2 4
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.
