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

Search Holiday Rentals near the Heart of the City in Maidenhead

Book self-catering holiday rentals for couples in Maidenhead to enjoy private, intimate dining spaces during your city break.

Food Lovers By Windsor And Heathrow With Secure Free Parking And Wifi - Maidenhead
8.8 4 reviews

Food Lovers By Windsor And Heathrow With Secure Free Parking And Wifi

apartment, Farnham Royal
This one-bedroom flat is located in Farnham Royal, offering free private parking and convenient access to local amenities.
This 50 square meter apartment provides a private entrance, free WiFi, a fully equipped kitchen, and accommodates up to seven guests.
Two Bedroom Apartment - Maidenhead
9.3 22 reviews

Two Bedroom Apartment

apartment, Slough
This two-bedroom flat is located in Slough, just 5.5 kilometres from Windsor Castle and 7 kilometres from Legoland Windsor, making it a great base for exploring the area. The surrounding area is quiet and peaceful, offering a relaxing stay for families or groups.
The flat is 74 square metres in size, with two bedrooms, one bathroom, and a living room, comfortably accommodating up to seven guests. The flat comes with free parking, Wi-Fi, a private balcony, a fully equipped kitchen, and modern amenities like a satellite flat-screen TV and a walk-in shower.
Stunning 2br Flat With Balcony - Maidenhead
10 2 reviews

Stunning 2br Flat With Balcony

apartment, London
This two-bedroom flat in Maidenhead is located 7.3 kilometres from Windsor Castle and 11.3 kilometres from Cliveden House, offering convenient access to local attractions.
This self-catering apartment covers 66 square metres, accommodates up to five guests with two bathrooms, and includes a dishwasher, microwave, fridge, and complimentary WiFi, with a private balcony for outdoor space.
Entr - Modern Apartments In Windsor - Maidenhead
8.8 410 reviews

Entr - Modern Apartments In Windsor

apartment, Windsor
These modern apartments are located in Windsor, just 3.2km from Legoland Windsor and 2.6km from Windsor Castle, making them ideal for exploring the town's attractions. They have received excellent ratings for location, cleanliness, and overall user experience.
Each apartment features two bedrooms, a comfortable living area with a sofa and flat-screen TV, and a fully equipped kitchen with a dining area. Enjoy the convenience of a dishwasher, oven, toaster, kettle, and complimentary Wi-Fi, as well as private on-site parking.

Best Maidenhead holiday rentals with air conditioning

Escape From The City - Maidenhead
9.3 9 reviews

Escape From The City

house, High Wycombe
This High Wycombe holiday home enjoys a peaceful countryside setting, approximately 10km from Cliveden House and within a 22km radius of Windsor Castle and Uxbridge.
Sleeping up to 7 guests, this self-catering property boasts a fully equipped kitchen with dishwasher, private garden, free Wi-Fi, and parking; towels and linen are available at an extra cost.
35 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests - Maidenhead
10 1 review

35 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests

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.
Willow Court Farm Studio West & Petting Farm, 8 Mins To Legoland & Windsor, 15 Mins To Lapland Uk - Maidenhead
9.7 193 reviews

Willow Court Farm Studio West & Petting Farm, 8 Mins To Legoland & Windsor, 15 Mins To Lapland Uk

studio, Windsor
This studio apartment is situated in Windsor, just 2.1 kilometres from Legoland Windsor and 4.2 kilometres from Windsor Castle, offering easy access to the region's popular attractions.
The 33 square metre studio features a fully equipped kitchen with a fridge, microwave oven, and dishwasher, a terrace, a garden, and parking, accommodating up to 5 guests and providing a peaceful retreat on a farm with opportunities to interact with animals.
Cosy One Bedroom Apartment In Marlow Bottom - Maidenhead
No reviews

Cosy One Bedroom Apartment In Marlow Bottom

apartment, Marlow
This one-bedroom flat is located in Marlow Bottom, offering proximity to Cliveden House (9 kilometres) and Dorney Lake (17.7 kilometres).
This apartment for 5 guests includes a private balcony, a fully equipped kitchen with a dishwasher and oven, complimentary Wi-Fi, and a washing machine, with a check-out time of 12:00 PM.

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.

Popular destinations

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.

Spacious 2br With Balcony - Slough - Maidenhead
No reviews

Spacious 2br With Balcony - Slough

apartment, Slough
This Slough flat is located 5.9 kilometres from Windsor Castle and 6.9 kilometres from Legoland Windsor.
This spacious one-bedroom flat offers accommodation for up to eleven guests, featuring a private balcony with city views, a dishwasher, free WiFi, and on-site amenities including a terrace and outdoor seating.
2bed 2bath Bliss, Private Parking - By Tempstay - Maidenhead
8.0 3 reviews

2bed 2bath Bliss, Private Parking - By Tempstay

apartment, Windsor
This Windsor apartment, located 1.6km from Windsor Castle and 2.6km from Legoland Windsor, offers easy access to major attractions.
The 175 square metre property features two bedrooms, two bathrooms, a fully equipped kitchen with dishwasher, and a private balcony and garden, comfortably accommodating up to five guests.
Victorian Cottage, Close 2 All Sights, Parking - Maidenhead
9.2 11 reviews

Victorian Cottage, Close 2 All Sights, Parking

apartment, Berkshire
This charming Victorian house is located on a quiet residential road in Windsor, just a short walk from the town centre and a 5km drive to Legoland. The property has received excellent reviews from previous guests.
The two-bedroom house can accommodate up to four guests and features a fully equipped kitchen, a private garden, and a driveway with parking for one car. It also has free high-speed Wi-Fi, SKY Glass TV with Netflix and smart apps, and a device that monitors the environment inside the property.
Stylish 1br Flat | Central Windsor - Maidenhead
No reviews

Stylish 1br Flat | Central Windsor

apartment, Windsor
This Windsor city centre flat is conveniently located near King Edward Court Shopping Centre, the River Thames, and within 4.8km of Windsor Castle and LEGOLAND Windsor.
The 58 square metre self-catering apartment offers one bedroom, one bathroom, sleeps four guests, and includes a fully equipped kitchen with fridge, microwave, dishwasher and washing machine, plus a TV with DVD player and a sofa bed.

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.

Bright And Airy Apartment In Unbeatable Location! - Maidenhead
9.6 89 reviews

Bright And Airy Apartment In Unbeatable Location!

apartment
This one-bedroom flat is located just 500 metres from Windsor town centre and the River Thames, offering a quiet retreat away from the hustle and bustle. It has consistently received excellent ratings for location, cleanliness, and user experience.
The flat can comfortably accommodate up to four guests and includes a well-equipped kitchen with a fridge, freezer, microwave, and dishwasher. Guests can enjoy free parking, high-speed internet, a communal garden, and a range of amenities for a comfortable stay.
Charming 2 Bed Apt | Windsor - Vat Q - By Tempstay - Maidenhead
8.0 2 reviews

Charming 2 Bed Apt | Windsor - Vat Q - By Tempstay

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.
Smart Loft Annex In Cookham - Maidenhead
9.8 123 reviews

Smart Loft Annex In Cookham

apartment
This first-floor apartment is located on a quiet lane just a few minutes' walk from Cookham High Street, with its many pubs and restaurants, and is also within easy reach of the River Thames towpath. The apartment has received excellent ratings for its location, cleanliness, and user experience.
This loft annex can accommodate up to 3 guests and features a private entrance, a dedicated parking space, and comfortable furnishings. The apartment offers a range of amenities, including SkyTV with Sky Cinema, Sky Kids, Sky/BT Sports, fast Wi-Fi, and a sheltered lawn area with a table and benches for alfresco dining.
Spacious Central Slough Sleep 6 W Balcony - Maidenhead
No reviews

Spacious Central Slough Sleep 6 W Balcony

apartment, Slough
This flat in central Slough offers convenient access to major transport links and attractions, situated 5 kilometres from Windsor Castle, 6.9 kilometres from Legoland Windsor, and 12.1 kilometres from London Heathrow Airport.
This 556 square meter residence accommodates up to 6 guests with 1 bedroom and 1 bathroom, featuring a fully equipped kitchen, free WiFi, a work desk, and a private balcony with city views, alongside a sun terrace.

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.

Kensington House By Mnk Estates - Maidenhead
7.9 316 reviews

Kensington House By Mnk Estates

apartment, Slough
Eton Bridge Apt- Walk Sights- Parking By Tempstay - Maidenhead
10 2 reviews

Eton Bridge Apt- Walk Sights- Parking By Tempstay

apartment, Eton
Crown Mews, Including Parking Windsor Centre - Maidenhead
10 5 reviews

Crown Mews, Including Parking Windsor Centre

apartment, Windsor
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

Explore 5-Star Self-Catering Rentals in Maidenhead

Upscale holiday rentals in Maidenhead offer a refined stay you will want to return to. Enjoy premium amenities and attentive service.

Stylish 1br Flat, Central Windsor - Maidenhead
8.7 79 reviews

Stylish 1br Flat, Central Windsor

apartment, Windsor

Top Pet-Friendly Holiday Rentals in Maidenhead

These dog-friendly holiday rentals in Maidenhead feature city walks on the doorstep. Your dog will love the trip as much as you do.

Maidenhead Fabulous Stylish Two Bedroom Penthouse - Maidenhead
9.1 9 reviews

Maidenhead Fabulous Stylish Two Bedroom Penthouse

apartment
Maidenhead Fabulous Stylish Two Bedroom Penthouse - Maidenhead
No reviews

Maidenhead Fabulous Stylish Two Bedroom Penthouse

apartment, Maidenhead
Cosy Cookham Cottage - Maidenhead
9.6 15 reviews

Cosy Cookham Cottage

apartment
Modern 2 Bedroom With Parking In Central Windsor Next To Castle & Shops - Maidenhead
8.3 4 reviews

Modern 2 Bedroom With Parking In Central Windsor Next To Castle & Shops

apartment, Windsor

Choose the Right Holiday Rentals with a Pool in Maidenhead

Pool access at your holiday rental makes a proper swim in the heart of the city part of your daily routine in Maidenhead.

Romantic 3beds Yacht Escape On Thames - Maidenhead
No reviews

Romantic 3beds Yacht Escape On Thames

apartment, Staines
Entertain, Celebrate, Relax In Period Luxury Barn - Perfect For Family Groups - Maidenhead
10 14 reviews

Entertain, Celebrate, Relax In Period Luxury Barn - Perfect For Family Groups

apartment, Taplow
4 Bed In Bray (Oc-b32610) - Maidenhead
No reviews

4 Bed In Bray (Oc-b32610)

cottage, Bray
Forest Getaway - Countryside Retreat Near Windsor - Maidenhead
10 2 reviews

Forest Getaway - Countryside Retreat Near Windsor

house, Hedgerley

Guest-Favourite Holiday Rentals with a Hot Tub in Maidenhead

Whether you prefer a jacuzzi or a hot tub, these holiday rentals in Maidenhead include one for your private use. See what catches your eye now.

Luxury New Build 5-bed Bungalow-long Stay Offer - Maidenhead
9.2 7 reviews

Luxury New Build 5-bed Bungalow-long Stay Offer

house, Winkfield
Superb 4 Bed Home In The Windsor Tapestries By Casa By Grace - Sleeps 7-9, Private Hot Tub Hire, Free Parking, Dog Friendly, Legoland, Windsor Castle - Maidenhead
9.8 102 reviews

Superb 4 Bed Home In The Windsor Tapestries By Casa By Grace - Sleeps 7-9, Private Hot Tub Hire, Free Parking, Dog Friendly, Legoland, Windsor Castle

house, Windsor
Stunning Place Near Windsor & Heathrow, 3br House - Maidenhead
10 1 review

Stunning Place Near Windsor & Heathrow, 3br House

apartment, Burnham
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
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