Best Holiday rentals and Airbnb offers in Maidenhead
8.0 2 reviews
Maidenhead
16/07 – 23/07
SG$262/nighttotal: SG$1834 (7 )
Cosy Central Apartment In Windsor By Tempstay
1 1
apartment , Berkshire
This Windsor apartment, an 8-minute walk from Windsor Castle and the Long Walk, offers easy access to Eton Bridge (2.4km) and Legoland Windsor (approx. 5km by car). The one-bedroom flat, sleeping up to three guests, includes a fully equipped kitchen, modern bathroom, private balcony, free on-site parking, and is conveniently located for London train connections (30 minutes to Paddington).
7.3 3 reviews
Maidenhead
28/07 – 04/08
SG$514/nighttotal: SG$3598 (7 )
3 Bedroom Apt.04 With Parking In Maidenhead
3 6
apartment , Maidenhead
This three-bedroom, two-bathroom Maidenhead flat is a 0.24km walk from Maidenhead train station, offering easy access to Central London within 30 minutes by train. The 75m² self-catering property features an open-plan living/dining area, a fully equipped kitchen with freezer and microwave, free secured gated parking, and accommodates up to six guests; weekly linen and towel changes are standard.
9.8 68 reviews
Maidenhead
16/07 – 23/07
SG$334/nighttotal: SG$2338 (7 )
The Lookout - 2 Beds, Private Garden & Parking
2 1
apartment , Knowl Hill
The Lookout, a self-contained annex in Knowl Hill Common, Berkshire, is conveniently located approximately 16km from Henley-on-Thames, Marlow, and Maidenhead, and 32km from Windsor. This two-bedroom property sleeps five, offering a fully equipped kitchen, private walled garden, hypoallergenic bedding, parking for two cars, and amenities including Wi-Fi and a smart TV; a mid-stay clean is included for bookings exceeding two weeks.
8.8 19 reviews
Maidenhead
28/07 – 04/08
SG$413/nighttotal: SG$2891 (7 )
Corporate Stay With Free Parking & Reliable Wi-fi
1 6
apartment , Berkshire
This four-bedroom house on Farnham Road, Slough, Berkshire, is situated 11km from Slough Railway Station, 11km from the River Thames, and 19km from Heathrow Airport, offering easy access to Windsor Castle. The spacious property sleeps eight guests, features three bathrooms, a fully equipped kitchen, free Wi-Fi, Netflix, and free parking, making it ideal for families, business travellers, or contractors.
Maidenhead
01/07 – 29/07
SG$286/nighttotal: SG$8008 (28 )
Detached Bungalow, Rural Location, Large Garden
1 2
apartment , Dorney Reach
This detached bungalow in Dorney Reach is situated in a tranquil village by the River Thames, offering convenient access to Eton (8 km drive), Windsor (12 km drive), and Legoland (16 km drive), with London accessible in 30 minutes by train from Taplow station (4 km drive). The property features a spacious open-plan living and dining area, accommodates up to 8 guests, includes a garden, ample parking for 4 cars, and provides direct access to walks along the River Thames and Jubilee River.
9.9 320 reviews
Maidenhead
14/08 – 16/08
SG$233/nighttotal: SG$466 (2 )
Cosy Garden Cabin • Near Windsor Castle & Legoland
1 2
cabin , Windsor
This charming cabin is located in a quiet residential area of Windsor, just 1.5-2 km from the town centre, Windsor Castle, and the train station. The cabin has consistently received excellent ratings from guests for its cleanliness, location, and overall experience. This cosy dwelling features one bedroom and one bathroom, comfortably accommodating up to four guests. The cabin offers a well-equipped kitchenette, a private garden, secure bike storage, and modern amenities such as Wi-Fi and a Smart TV.
Maidenhead
28/07 – 04/08
SG$3018/nighttotal: SG$21126 (7 )
4 Bed In Bray (Oc-b32610)
4 6
cottage , Bray
This four-bedroom lodge is situated in Maidenhead, 500 meters from the River Thames and a seven-minute drive from Bray Marina. The property offers accommodation for eight guests, featuring a kitchen, swimming pool, jacuzzi, garden, and on-site parking, with complimentary Wi-Fi and television provided.
9.8 156 reviews
Maidenhead
14/08 – 16/08
SG$210/nighttotal: SG$420 (2 )
Wisteria, Barn Conversion In Stunning Location
1 2
apartment , Buckinghamshire
This self-contained flat is located in Dorney, a peaceful village just 5 kilometres from Windsor and Legoland, offering easy access to these popular attractions. The apartment has consistently received excellent ratings for cleanliness, location and user experience. The flat has a separate double bedroom, shower room and kitchen, making it perfect for a couple or a small family of up to four people. Guests will enjoy the modern kitchen, private garden, and proximity to the Thames tow path and Dorney Rowing Lake, ideal for outdoor activities.
9.4 21 reviews
Maidenhead
01/07 – 31/08
SG$564/nighttotal: SG$34404 (61 )
Tranquil Retreat: Modern Flat In Maidenhead
1 1
apartment , Berkshire
This ground floor flat is located in Maidenhead, just 100 metres from the train station with direct connections to Paddington station in London. The one-bedroom apartment offers a private entrance, an open-plan lounge and kitchen, and is ideal for couples wanting to explore Berkshire's attractions including Windsor Castle and Legoland Windsor, both within a 20-minute drive.
9.4 5 reviews
Maidenhead
16/07 – 23/07
SG$281/nighttotal: SG$1967 (7 )
Tranquil Garden Haven, Comfy Family & Contractor Pad
2 1
house , Farnham Royal
This family-friendly holiday home in Farnham Royal offers convenient access to Windsor Castle (6.6 kilometres) and Dorney Lake (7.9 kilometres), with Legoland Windsor (8.2 kilometres) and Cliveden House (9.2 kilometres) also nearby. This two-bedroom property accommodates up to nine guests and features a kitchen with a fridge and microwave, complimentary on-site parking, free WiFi, and a private garden, with airport transfer arrangements available.
9.6 5 reviews
Maidenhead
28/07 – 04/08
SG$460/nighttotal: SG$3220 (7 )
Spacious Family Home Near Windsor, Free Parking
5 6
apartment , Berkshire
This five-bedroom house in Slough, Berkshire, offers convenient access to the Thames Valley area, situated approximately 30 kilometers west of central London. This spacious property accommodates up to nine guests with a fully equipped kitchen, a garden with a patio, a dedicated workspace, and free on-site parking, ideal for families or groups seeking self-catering accommodation with garden access.
9.9 16 reviews
Maidenhead
14/08 – 16/08
SG$310/nighttotal: SG$620 (2 )
Cosy & Homely Stay In Maidenhead
1 2
apartment , Berkshire
This Maidenhead apartment, a short walk from the town centre and Maidenhead railway station, offers easy access to Braywick Nature Reserve and is a short drive (approximately 8km) from Windsor. The two-bedroom, two-bathroom flat sleeps four, includes a fully equipped kitchen with dishwasher, private parking, and internet access, and is ideally located for exploring Berkshire's attractions.
Best family friendly Maidenhead holiday rentals
Among the 304 accommodations in Maidenhead, here are the 4 best family friendly rentals
9.1 19 reviews
Maidenhead
14/08 – 16/08
SG$197/nighttotal: SG$394 (2 )
Meadow View
2 2
house , Hurst
This Hurst, Berkshire holiday home is situated approximately 16km from LaplandUK and 19km from Legoland Windsor, offering easy access to popular family attractions. The one-bedroom property sleeps four guests, features a fully equipped kitchen, a terrace, free private parking, and a flat-screen TV.
9.8 74 reviews
Maidenhead
28/07 – 04/08
SG$1062/nighttotal: SG$7434 (7 )
Incredible Central Windsor, Free Parking + Garden
1 6
apartment , Berkshire
This five-bedroom house is situated in Windsor's Golden Triangle, a 0.8km walk from Windsor Castle and close to Windsor town centre, with Legoland Windsor a 5-minute (approx. 4km) drive away and Ascot Racecourse just over a 10-minute (approx. 8km) drive. The property boasts a fully equipped kitchen, double living room with a football table, free Wi-Fi and Netflix, sleeps 10 guests, and includes a private garden and resident parking permit (additional vehicles at a fee).
9.4 6 reviews
Maidenhead
16/07 – 23/07
SG$324/nighttotal: SG$2268 (7 )
1br|parking|doorstep Of Windsor Castle|by Tempstay
1 1
apartment , Berkshire
This Windsor city centre flat is ideally located less than 1.6km from Windsor Castle and Windsor Guildhall, and a short walk from Windsor & Eton Central and Riverside train stations, offering easy access to LEGOLAND® Windsor (4.2km). The one-bedroom apartment sleeps two guests and features a fully equipped kitchen with oven, microwave, and stovetop, plus a washing machine, TV, hairdryer, parking, and internet access.
Maidenhead
16/07 – 23/07
SG$374/nighttotal: SG$2618 (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.
Best Maidenhead holiday rentals with parking
8.4 52 reviews
Maidenhead
14/08 – 16/08
SG$252/nighttotal: SG$504 (2 )
Floating Tranquility
2 2
boat , Dorney
This Dorney floating lodge is situated near Windsor Castle (4.3km), Legoland Windsor (4.7km), and Dorney Lake (13.4km), offering convenient access to major attractions. The 46-square-metre vessel boasts one bedroom, two bathrooms, and accommodates up to five guests, featuring a private terrace, garden, air conditioning, parking, and an electric vehicle charging station.
Maidenhead
28/07 – 04/08
SG$821/nighttotal: SG$5747 (7 )
Windsor 5-bed House - Near Castle - Sleeps 13
5 6
apartment , Greater London
This five-bedroom residence is located in a quiet residential close in Windsor, approximately 1.6 kilometres from Windsor Castle and the town centre, with easy access to Legoland, Ascot Racecourse and Heathrow Airport, all within a 3.2 to 6.4 kilometre drive. This spacious 300 square metre, three-floor property accommodates up to 9 guests comfortably, with a potential for 13, featuring an open-plan kitchen, dining and living area, a private garden, and a games room with a pool table.
10 1 review
Maidenhead
14/08 – 16/08
SG$270/nighttotal: SG$540 (2 )
Chic Studio Steps From Windsor Castle
1 2
studio , Windsor
This Windsor city centre flat is conveniently located near King Edward Court Shopping Centre and the River Thames, within 4.8km of Windsor Castle and LEGOLAND Windsor. The one-bedroom apartment sleeps two guests and features a fully equipped kitchen with fridge and dishwasher, a washing machine, a dining area, a TV, and on-site parking.
Maidenhead
01/07 – 31/08
SG$205/nighttotal: SG$12505 (61 )
Apt - Sleeps 2 - Parking - Wifi
1 1
apartment , Slough
This one-bedroom flat is situated in Slough, just a short distance from the River Thames and within easy reach of popular attractions like LEGOLAND® Windsor and Thorpe Park. The surrounding area offers a mix of residential and commercial properties, providing a convenient location for exploring the region. The 40 square meter flat comfortably sleeps two guests and features a well-equipped kitchen, a spacious living area, and a modern bathroom. The flat also includes amenities such as free parking, high-speed internet, and a washing machine, making it a great choice for families or couples looking for a comfortable and convenient base in Slough.
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
9.2 410 reviews
Maidenhead
14/08 – 16/08
SG$300/nighttotal: SG$600 (2 )
Hampden Apartments - The Edward
1 2
apartment , Windsor
The Hampden Apartments - The Edward is situated just a short walk from Windsor Castle and a 10-kilometre drive from Legoland Windsor and Thorpe Park, making it a convenient base for exploring the town and its surrounding attractions. Guests have consistently rated the apartment highly for its location, cleanliness, and overall experience. This one-bedroom apartment offers 50 square metres of space, comfortably accommodating up to four guests. The apartment comes equipped with a fully fitted kitchen, a private balcony, and free on-site parking, ensuring a comfortable and enjoyable stay.
Maidenhead
28/07 – 04/08
SG$497/nighttotal: SG$3479 (7 )
Windsor Gem:3 Bed|2 Bath|parking - By Tempstay
3 6
apartment , Windsor
This Windsor City Centre flat is a 10-minute walk from Windsor Castle and shops, and within a short drive (3.8km) of Legoland Windsor Resort. The 4-bedroom, 2-bathroom apartment sleeps 6, boasts a private terrace, complimentary parking, and includes a microwave and dishwasher; nearby attractions include Eton College (3.2km) and Ascot Racecourse (10.7km).
10 1 review
Maidenhead
16/07 – 23/07
SG$366/nighttotal: SG$2562 (7 )
Charming 2 Bed Apt | Windsor - Vat Q - By Tempstay
2 1
apartment , Berkshire
This Clewer East apartment, situated within 3.2km of Windsor Castle and LEGOLAND Windsor, offers easy access to the River Thames and King Edward Court Shopping Centre. The two-bedroom, two-bathroom property sleeps three guests and includes a well-equipped kitchen with dishwasher, a washing machine, and a private garden with parking; nearby attractions include the Thames Path.
Maidenhead
28/07 – 04/08
SG$883/nighttotal: SG$6181 (7 )
Bray - 6 Bedroom Detached Family House - Gated Parking For 6 Cars, Sleeps 11, Bray, Maidenhead
6 6
house , Maidenhead
This detached family house in Ascot, Maidenhead, is located 7.2 kilometres from Dorney Lake and 7.7 kilometres from Cliveden House, with Windsor Castle 9.8 kilometres away. This property offers 277 square meters of living space, accommodating up to 11 guests with four bathrooms, a fully equipped kitchen, and gated parking for six vehicles, complemented by free WiFi and proximity to public transport.
Best Maidenhead holiday rentals with air conditioning
9.4 125 reviews
Maidenhead
14/08 – 16/08
SG$168/nighttotal: SG$336 (2 )
The Studio On The Green
1 2
studio , Egham
The Studio on The Green is conveniently located in Egham, just 8km from Thorpe Park, 12km from LaplandUK, 8km from Windsor Castle and 9.5km from Legoland Windsor. The studio has received excellent ratings for location, cleanliness and overall experience from previous guests. This self-contained apartment has one bedroom and can accommodate up to two guests. Enjoy a private garden, free Wi-Fi, parking, air conditioning, a fully equipped kitchenette, and a private entrance.
Maidenhead
14/08 – 16/08
SG$327/nighttotal: SG$654 (2 )
Lovely Cottage In Beautiful Berkshire Near Ascot
2 2
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.
Maidenhead
28/07 – 04/08
SG$329/nighttotal: SG$2303 (7 )
3 Bed For 8 Apartment In The Centre Of Slough
3 6
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.
Maidenhead
16/07 – 23/07
SG$318/nighttotal: SG$2226 (7 )
Page 256 By Ja'mo With King Bed And Free Parking
1 1
apartment , Slough
This one-bedroom apartment is located in Slough, just 1.5 km from Absolutely Ice - Slough Ice Arena and within a 5 km radius of both Eton College and Eton High Street Shopping. It's a great base for exploring the area, with easy access to both the town centre and nearby attractions. The apartment can accommodate up to 3 guests and features a fully equipped kitchen, a comfortable living space, and a modern bathroom. Enjoy the convenience of a spa tub, free WiFi, and a Smart TV, perfect for a relaxing stay.
