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Maidenhead vacation rentals
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Best Vacation rentals and Airbnb offers in Maidenhead

Compare Vacation Rentals for Families in Maidenhead

Booking a family-oriented vacation rental in Maidenhead keeps you close to top city attractions for a stress-free getaway.

Friends & Families | Parking & Ev | Station Nearby - Maidenhead
10 67 reviews
Maidenhead
10/10 – 10/17
$266/nighttotal: $1862 (7 )

Friends & Families | Parking & Ev | Station Nearby

1 4
apartment , Berkshire
This top-floor apartment is located in Maidenhead, a short walk from the town center and train station, making it easy to explore the area's attractions. It's also close to picturesque towns like Marlow, Henley, Windsor, and Legoland. The apartment has three bedrooms, comfortably sleeping up to six guests, making it perfect for families or groups of friends. It features modern amenities like a dishwasher, washing machine, dryer, and flat-screen TVs, ensuring a comfortable stay.
Keel Drive Modern 3-bedroom, 2-bathroom Home - Maidenhead
9.5 2 reviews
Maidenhead
06/24 – 07/17
$260/nighttotal: $5980 (23 )

Keel Drive Modern 3-bedroom, 2-bathroom Home

3 4
house , Slough
This three-bedroom house in Slough, Berkshire, is conveniently located 9.3 miles from London Heathrow Airport, offering easy access to air travel.
The 680-square-foot (approximately 63 square meters) home features two bathrooms, free Wi-Fi, free private parking, and accommodates up to 10 guests, making it ideal for families or groups visiting Slough.
Magnolia Penthouse - Maidenhead
9.2 55 reviews
Maidenhead
10/12 – 10/18
$188/nighttotal: $1128 (6 )

Magnolia Penthouse

2 2
apartment , Windsor
The Magnolia Penthouse is a centrally located Windsor apartment, a 9-minute walk from Windsor Castle and 2.2 miles from Legoland Windsor.
This 650-square-foot (60-square-meter) two-bedroom, one-bathroom rental sleeps seven, features free Wi-Fi, free parking, a full kitchen with oven and microwave, and a washing machine.
3 Bedroom Sleeps 5 Central Windsor With Parking - Maidenhead
9.9 166 reviews
Maidenhead
07/28 – 08/04
$374/nighttotal: $2618 (7 )

3 Bedroom Sleeps 5 Central Windsor With Parking

1 4
apartment , Berkshire
The Burrow, a three-bedroom maisonette in central Windsor, Berkshire, offers convenient access to Windsor High Street, the River Thames, and Windsor Castle, all within walking distance.
This recently refurbished dwelling sleeps up to five guests in a spacious three-floor layout, boasting a well-equipped kitchen, a bathroom with a walk-in shower, free off-street parking for one car, and individually designed bedrooms.

Best Maidenhead vacation rentals with parking

Contemporary Boutique 4 Sleeper Eton High Street - Pass The Keys - Maidenhead
8.6 9 reviews
Maidenhead
07/28 – 08/04
$220/nighttotal: $1540 (7 )

Contemporary Boutique 4 Sleeper Eton High Street - Pass The Keys

1 4
apartment , Windsor
This Windsor apartment rental is located in Eton, a 4-minute walk from Windsor Castle and close to Legoland Windsor and Heathrow Airport.
The 600-square-foot (56-square-meter) unit features one bedroom, one bathroom, sleeps four, and includes a fully equipped kitchen with a fridge, microwave, and dishwasher, plus free private parking—a valuable amenity in Windsor.
Cosy Coach House Near Henley & Marlow - Maidenhead
9.9 92 reviews
Maidenhead
06/20 – 06/27
$253/nighttotal: $1771 (7 )

Cosy Coach House Near Henley & Marlow

1 2
cabin , Berkshire
The Coach House Studio is a stylish one-bedroom apartment located near the picturesque villages of Wargrave, Twyford, Henley-on-Thames, and Marlow, offering easy access to the River Thames and surrounding countryside. The property has received excellent ratings for location, cleanliness, and overall guest experience.
The studio features a private entrance, a king-size bed, a cozy sofa, and a well-equipped kitchenette. Guests can enjoy access to a shared outdoor pool, a fire pit, and a BBQ, perfect for relaxing and enjoying the beautiful Berkshire countryside.
Perfect Location, 1 Bedroom Apt, Castle, Legoland - Maidenhead
8.0 15 reviews
Maidenhead
06/20 – 06/27
$154/nighttotal: $1078 (7 )

Perfect Location, 1 Bedroom Apt, Castle, Legoland

1 2
apartment , Windsor
This Windsor apartment rental is conveniently located 1.2 miles from Legoland Windsor and 1.8 miles from Windsor Castle, offering easy access to major attractions.
The 700-square-foot unit features one bedroom, one bathroom, a fully equipped kitchenette, and a private garden, comfortably accommodating up to five guests and including free Wi-Fi and on-site parking.
Willow Court Farm Studio West & Petting Farm, 8 Mins To Legoland & Windsor, 15 Mins To Lapland Uk - Maidenhead
9.6 123 reviews
Maidenhead
06/18 – 06/19
$334/nightfor 1 night

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

1 2
studio , Windsor
This Windsor studio is located on a farm just 8 minutes from Legoland and Windsor, and 15 minutes from Lapland UK.
The 360 square foot studio features a fully equipped kitchen, a terrace, and a garden, and can accommodate up to 5 guests.

Frequently Asked Questions about vacation rentals in Maidenhead

  • Which neighborhood in Maidenhead should you consider for a vacation rental?

    The best neighborhood for a vacation rental is probably around the town center, as it's close to shops, restaurants, and the train station. You'll be within walking distance of everything and have easy access to all the attractions Maidenhead has to offer.
  • What are the best Airbnb and vacation rentals in Maidenhead?

  • What are the top family-friendly attractions in Maidenhead?

    For families, the Maidenhead Heritage Centre is a great place to learn about the town's history, and the Maidenhead Thicket is a beautiful park with plenty of space for kids to run around. The Braywick Leisure Centre has a pool, gym, and other activities for all ages.
  • What are the most popular Airbnbs 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, like spring or fall, when the weather is mild and the crowds are smaller. You'll get the best deals and have a more relaxed experience.
  • What are the best vacation rentals with a pool in Maidenhead?

    Spacious Sunny Apartment, Sheephouse Manor and Modern Bungalow With Private Swimming Pool are the best vacation rentals with a pool in Maidenhead.

  • What events or festivals should visitors check out in and around Maidenhead?

    Maidenhead doesn't have many large festivals, but you can check out the Maidenhead River Festival in July for live music, food stalls, and boat races. The nearby Windsor Castle also hosts many events throughout the year.
  • What are the best rentals for families and kids in Maidenhead?

  • What are the best budget-friendly activities in Maidenhead?

    For budget-friendly activities, you can walk or cycle along the Thames Path, visit the free Maidenhead Library, or explore the Maidenhead Thicket. The town center also has many affordable cafes and restaurants.
  • What are the best rentals or Airbnbs with a jacuzzi in Maidenhead?

  • What are the best restaurants with local dishes in Maidenhead?

    The best restaurants for local dishes are probably The Old House at 42, which serves traditional British pub food, and The Copper Kettle, which has a more modern take on British cuisine. For a more casual experience, you can try The Anchor pub.
  • What are the best walking or cycling routes in Maidenhead?

    A great walking or cycling route is along the Thames Path, which goes right through Maidenhead. You can also explore the Maidenhead Thicket, which has many trails for all levels of fitness.
  • Are there pet-friendly attractions in Maidenhead?

    Maidenhead Thicket is pet-friendly and a great place for a walk with your dog. Many of the cafes and restaurants in the town center also welcome dogs.
  • What are the benefits of choosing a vacation rental in Maidenhead?

    Vacation rentals offer more space and privacy than a hotel. You can also cook your own meals and enjoy the amenities of a home away from home. Some vacation rentals even have unique features like a hot tub or a garden.

Destinations nearby

Choose the Right Vacation Rentals with a Terrace in Maidenhead

Enjoy your own private terrace with city skyline views at these vacation rentals in Maidenhead.

Hampden Apartments - The Anne - Maidenhead
9.0 183 reviews
Maidenhead
10/12 – 10/18
$230/nighttotal: $1380 (6 )

Hampden Apartments - The Anne

1 2
apartment , Windsor
The Hampden Apartments - The Anne is located in Windsor, just a short walk from Windsor Castle and within easy reach of Legoland Windsor, making it a great base for exploring the area. This apartment has excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
This 1-bedroom apartment is spacious, with a floor area of 750 square feet, and can accommodate up to 4 guests. It features a fully equipped kitchen, a private balcony with city views, free Wi-Fi, and private parking, providing everything you need for a relaxing and convenient stay.
Riverwalk Apartment North - Maidenhead
8.8 16 reviews
Maidenhead
06/20 – 06/27
$436/nighttotal: $3052 (7 )

Riverwalk Apartment North

2 2
apartment , Datchet
Riverwalk Apartment North in Datchet offers a 1,000-square-foot rental, 1.6 miles from Windsor Castle and 4.4 miles from Legoland Windsor.
This two-bedroom, one-bathroom unit sleeps 13, features a fully equipped kitchen, private parking, and access to on-site amenities including a fitness center, sun terrace, and barbecue, plus nearby water sports on the River Thames.
2-bdr Apt -Balcony-parking-near Castle By Tempstay - Maidenhead
Maidenhead
10/10 – 10/17
$248/nighttotal: $1736 (7 )

2-bdr Apt -Balcony-parking-near Castle By Tempstay

2 4
apartment , Windsor
This Windsor apartment rental is located in Clewer East, an 11-minute walk from King Edward Court Shopping and a 2-minute drive from Windsor Castle, offering easy access to major attractions.
The two-bedroom, one-bathroom unit sleeps four guests and features a fully equipped kitchen, private garden, terrace, on-site parking, and amenities including Wi-Fi and a washing machine; nearby activities include cycling and horse riding.
Escape In Style| Windsor  - Vat Q - By Tempstay - Maidenhead
10 1 review
Maidenhead
06/21 – 06/29
$265/nighttotal: $2120 (8 )

Escape In Style| Windsor - Vat Q - By Tempstay

2 4
apartment , Berkshire
This Clewer East apartment rental is conveniently located within 2 miles of Windsor Castle, LEGOLAND Windsor, and the River Thames.
This two-bedroom, two-bathroom unit sleeps four guests and features a fully equipped kitchen, private balcony, access to a community garden, and parking; nearby attractions include King Edward Court Shopping Center and easy access to Windsor & Eton Central and Riverside train stations.

Best Maidenhead vacation rentals with air conditioning

The Studio - Large Bedroom & Kitchen Near Marlow - Maidenhead
10 2 reviews
Maidenhead
06/18 – 06/19
$189/nightfor 1 night

The Studio - Large Bedroom & Kitchen Near Marlow

1 2
apartment , Buckinghamshire
This studio apartment is located in a quiet area of Buckinghamshire, offering convenient access to local shops and outdoor activities.
This pet-friendly studio sleeps up to three guests, featuring a king-size bed, a sofa bed, a kitchenette with a microwave, air conditioning, and Wi-Fi, with parking available.
30 M² Apartment ∙ 1 Bedroom ∙ 2 Guests - Maidenhead
Maidenhead
10/12 – 10/18
$116/nighttotal: $696 (6 )

30 M² Apartment ∙ 1 Bedroom ∙ 2 Guests

1 2
apartment
This one-bedroom flat is located at 57 Farnham Road in Great Britain, offering convenient access to public transportation with a bus stop and supermarket within walking distance, and Slough train station just a short walk away, while a metro station is a 10-minute bike ride from this property. This 320 square foot apartment accommodates two guests and features air conditioning, high-quality furniture, a fully equipped kitchen, and a comfortable double bed, with rare free parking available in the neighborhood.
Period Luxury Converted Barn Windsor/maidenhead - Perfect For Family Groups - Maidenhead
9.3 3 reviews
Maidenhead
10/17 – 10/24
$2895/nighttotal: $20265 (7 )

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

9 4
house , Taplow
This eight-bedroom, seven-bathroom period barn conversion is located in Taplow, just 1.8 miles from Dorney Lake and five miles from Cliveden House.
This 5,930 square foot house features a private pool, hot tub, fitness center, and a bar, accommodating up to 29 guests and offering a convenient airport shuttle service to Heathrow Airport.
Luxury Smart Windsor London Parking - Maidenhead
10 1 review
Maidenhead
10/17 – 10/24
$188/nighttotal: $1316 (7 )

Luxury Smart Windsor London Parking

1 4
house , Farnham Royal
This vacation home is located 11 miles from London Heathrow Airport in Farnham Royal.
This 380-square-foot, 1-bedroom cottage offers air conditioning, Wi-Fi, a fully equipped kitchen, and parking for up to 9 guests.
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