Holiday Rentals in Maidenhead

445 available vacation rental offers

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Maidenhead holiday rentals
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Best Holiday rentals and Airbnb offers in Maidenhead

Best family friendly Maidenhead holiday rentals

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

1 Bedroom Garden Flat City Central Slough Near Windsor - Maidenhead
10 3 reviews

1 Bedroom Garden Flat City Central Slough Near Windsor

apartment, Slough
This Slough apartment, a peaceful garden flat centrally located near Windsor Castle (5.2km), Legoland Windsor (7.9km), and Brunel University (10.8km), offers a tranquil escape.
The 55 square metre one-bedroom flat sleeps nine, featuring a fully equipped kitchen with dishwasher, private terrace, free Wi-Fi, and in-unit laundry facilities.
Stylish 2 Bedroom Flat Slough - Maidenhead
8.1 6 reviews

Stylish 2 Bedroom Flat Slough

apartment, Slough
This two-bedroom flat in Moffat is situated 14.96 kilometres from London Heathrow Airport, 38.62 kilometres from Dumfries and County Golf Club, and 41.84 kilometres from Dumfries and Galloway Golf Club.
This Moffat apartment accommodates up to seven guests and offers a fully equipped kitchen, complimentary WiFi, and a flat-screen TV, with parking available for convenience.
Studio Flat - Maidenhead
8.7 38 reviews

Studio Flat

studio, Canvey
This Canvey Island guesthouse offers excellent value, situated conveniently near Windsor Castle (7.7km), Legoland Windsor (9.3km), and London Heathrow Airport (14km).
The 12-square-metre single-bedroom guest house provides free Wi-Fi, private parking, and sleeps one guest, with towels and linen included.
2br Apt Near Castle With Parking, Town Centre Location, Loft Room With Work Desk, 2cjh - Maidenhead
8.0 1 review

2br Apt Near Castle With Parking, Town Centre Location, Loft Room With Work Desk, 2cjh

apartment, Windsor
This two-bedroom Windsor flat offers a prime town centre location, just a 7-minute walk from Windsor Castle and 3.5 kilometres from Legoland Windsor.
This 86 square metre residence accommodates up to seven guests, featuring a dedicated workspace, a balcony, complimentary private parking, and a well-equipped kitchen with a dishwasher and oven, all within easy reach of transport links including London Heathrow Airport, 16 kilometres away.

Best Maidenhead holiday rentals with parking

Maidenhead Driveway Parking Garden - Maidenhead
9.5 8 reviews

Maidenhead Driveway Parking Garden

house, Maidenhead
This Leander apartment in Maidenhead enjoys a convenient location, approximately 13.5km from Windsor Castle, 14km from Legoland Windsor, 8km from Dorney Lake, and 8.4km from Cliveden House.
This 167 square metre, three-bedroom property with one bathroom offers private parking, a garden with patio views, satellite TV, and pet-friendly accommodation (additional charges apply).
Perfect Spot In Central Windsor & Free Parking! - By Tempstay - Maidenhead
9.1 143 reviews

Perfect Spot In Central Windsor & Free Parking! - By Tempstay

apartment, Windsor
This apartment is conveniently located in central Windsor, just a short walk from Windsor Castle and the town centre, making it ideal for exploring the area’s historical attractions. It has received very good ratings for cleanliness, location, and user experience, ensuring a comfortable and enjoyable stay.
The two-bedroom flat offers 65 square metres of space, comfortably accommodating up to six guests. It features a fully equipped kitchen, free parking, and modern amenities, including a flat-screen TV with streaming services, allowing you to relax and unwind after a day of exploring.
Oak Tree Studio - Maidenhead
8.8 74 reviews

Oak Tree Studio

studio, Marlow
This studio apartment is located just a short drive from the picturesque Chiltern Hills, offering easy access to stunning countryside walks and cycle paths. It has consistently received excellent ratings for cleanliness, location, and overall experience.
The studio apartment offers 40 square metres of space with a double bed, a sofa bed, and a four-seat dining table, comfortably accommodating up to three guests. It includes a private terrace, a fully equipped kitchen, a washing machine, freeview TV, Wi-Fi, and self check-in for added convenience.
The Royal Hideaway I Parking - Maidenhead
9.0 39 reviews

The Royal Hideaway I Parking

apartment, Windsor
Loft Living by Lawsons offers a one-bedroom apartment in Windsor, a 12-minute walk from Windsor Castle and 3.5km from Legoland Windsor.
This 51-square-metre flat, sleeping up to 7 guests, features a fully equipped kitchen with dishwasher, a private entrance, free Wi-Fi, and a terrace; nearby attractions include Dorney Lake and Thorpe Park.

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 most popular Airbnbs in Maidenhead?

  • 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.

Popular destinations

Best Maidenhead holiday rentals with a balcony

Central Windsor Gem | 1br Penthouse + Balcony - Maidenhead
8.4 5 reviews

Central Windsor Gem | 1br Penthouse + Balcony

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.
Maidenhead - 3 Bed House - Garden - Maidenhead
8.0 2 reviews

Maidenhead - 3 Bed House - Garden

house, Maidenhead
This three-bedroom house is located in Maidenhead, just under four miles from Dorney Lake and Cliveden House, and about 7.5 miles from Windsor Castle, making it an ideal base for exploring the local area. The property has consistently received excellent ratings for its cleanliness, location, and overall experience.
The spacious apartment offers 100 square metres of living space and can comfortably accommodate up to six guests. Enjoy a private garden, free Wi-Fi, a fully equipped kitchen, and access to streaming services, ensuring a comfortable and enjoyable stay.
Modern Apartment Within Short Walk Of The Castle, High Street And Long Walk - Free Parking - By Tempstay - Maidenhead
8.4 93 reviews

Modern Apartment Within Short Walk Of The Castle, High Street And Long Walk - Free Parking - By Tempstay

apartment, Windsor
This modern flat is situated just a short walk from Windsor Castle, the High Street, and Long Walk, offering easy access to the town's main attractions. The apartment has received very good user ratings, and excellent location and cleanliness ratings.
This self-catering property has one bedroom and one bathroom, and is suitable for up to three guests. It comes with free parking, a terrace, a garden, a fully equipped kitchen, and free Wi-Fi.
The Studio On The Green - Maidenhead
9.4 131 reviews

The Studio On The Green

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.

Best Maidenhead holiday rentals with air conditioning

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.
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.
Berkshire Cottage - Wellness Centre - Maidenhead
No reviews

Berkshire Cottage - Wellness Centre

house, Sunninghill
Berkshire Cottage - Wellness Centre is located in Sunninghill, 5.47 kilometres from LaplandUK and 10.46 kilometres from Legoland Windsor.
This wellness centre offers accommodation for up to 19 guests, featuring 1 bedroom, 4 bathrooms, a shared kitchen with a dishwasher and oven, air conditioning, a swimming pool, a terrace, a garden, and parking, with WiFi included.
Floating Tranquility - Maidenhead
8.4 64 reviews

Floating Tranquility

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.
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