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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.

Charming 2 Bdr In Windsor - Vat Q - By Tempstay - Maidenhead
Maidenhead
06/21 – 06/29
$249/nighttotal: $1992 (8 )

Charming 2 Bdr In Windsor - Vat Q - By Tempstay

2 4
apartment , Berkshire
This Clewer East apartment rental is located in Berkshire, England, less than 2 miles from Windsor Castle, LEGOLAND Windsor, and the River Thames.
The two-bedroom, two-bathroom unit sleeps four, features a fully equipped kitchen with dishwasher, in-unit laundry, and a private garden, plus parking; nearby attractions include King Edward Court Shopping and easy access to Windsor & Eton train stations.
Urban Heaven With Free Parking - Maidenhead
9.0 30 reviews
Maidenhead
08/10 – 08/20
$214/nighttotal: $2140 (10 )

Urban Heaven With Free Parking

2 1
apartment , Bracknell
This Bracknell apartment rental is conveniently located 2.9 miles from LaplandUK, with easy access to Legoland Windsor (8 miles), Windsor Castle (10 miles), and Thorpe Park (12 miles).
This 650-square-foot unit offers a spacious layout with two bedrooms, two bathrooms, and amenities including free parking, free Wi-Fi, a fitness center, and can comfortably accommodate up to nine guests.
Modern Windsor Home With Free Off-street Parking - Maidenhead
9.9 164 reviews
Maidenhead
10/10 – 10/17
$174/nighttotal: $1218 (7 )

Modern Windsor Home With Free Off-street Parking

1 4
apartment , Berkshire
This Windsor apartment rental is centrally located, a short walk from Windsor Castle and the High Street, offering easy access to the train station for convenient travel to London and Heathrow Airport.
The two-bedroom unit sleeps six guests comfortably, boasting a fully equipped kitchen with a fridge, microwave, and dishwasher, plus free parking—a rare find in central Windsor—and fast Wi-Fi.
Stable House - Eton Windsor - Maidenhead
9.5 226 reviews
Maidenhead
10/10 – 10/17
$303/nighttotal: $2121 (7 )

Stable House - Eton Windsor

2 4
house , Windsor
This charming house is located in Eton, just a short walk from Windsor Castle and a short drive from Dorney Lake and Legoland Windsor, offering easy access to the area's top attractions. The property has consistently received excellent ratings for its cleanliness, location, and overall user experience.
This two-bedroom vacation rental comfortably accommodates up to four guests and features a fully equipped kitchen, a private garden, and free WiFi. Enjoy modern amenities, unwind in the peaceful garden, and explore the nearby attractions.

Best Maidenhead vacation rentals with parking

Windsor 10 Mins - 3 Bedrooms, 2 Bathrooms House With Parking - By Tempstay - Maidenhead
8.5 2 reviews
Maidenhead
07/28 – 08/04
$356/nighttotal: $2492 (7 )

Windsor 10 Mins - 3 Bedrooms, 2 Bathrooms House With Parking - By Tempstay

3 6
apartment , Slough
This 3-bedroom apartment is located in Slough, just a short drive from Windsor and its attractions like Legoland Windsor, Brunel University, and Dorney Lake. The apartment has received very good ratings for location, cleanliness, and overall experience.
The apartment offers 1610 square feet of space, perfect for families or groups of up to 6 guests. It features a fully equipped kitchen, a relaxing garden, free parking, and modern amenities like free Wi-Fi, making it an ideal choice for a comfortable and convenient stay.
Hampden Apartments - The Richard - Maidenhead
9.3 252 reviews
Maidenhead
10/17 – 10/24
$335/nighttotal: $2345 (7 )

Hampden Apartments - The Richard

2 4
apartment , Windsor
The Hampden Apartments - The Richard is located in Windsor, just a 7-minute walk from Windsor Castle and a short distance from the town center, making it easy to explore the area's historic attractions and charming shops. This apartment consistently receives excellent ratings for its location, cleanliness, and overall experience.
The apartment has two bedrooms, a living room, and a fully equipped kitchen, providing plenty of space for families or groups of friends. Guests can enjoy a private balcony, free parking, a fitness center, and a garden, along with amenities like a dishwasher, microwave, and Wi-Fi.
2br Apt Near Windsor Castle Free Park By Tempstay - Maidenhead
Maidenhead
06/21 – 06/29
$232/nighttotal: $1856 (8 )

2br Apt Near Windsor Castle Free Park By Tempstay

2 4
apartment , Windsor
This Windsor apartment rental, located in the Clewer East district, is an 11-minute walk from King Edward Court Shopping and a 2-minute drive from Windsor Castle.
The two-bedroom, two-bathroom unit features a private garden and terrace, a fully equipped kitchen, in-unit laundry, Wi-Fi, and is close to LEGOLAND® Windsor and Thorpe Park.
Sheephouse Manor - Maidenhead
8.3 38 reviews
Maidenhead
07/28 – 08/04
$362/nighttotal: $2534 (7 )

Sheephouse Manor

3 6
house , Maidenhead
Sheephouse Manor is a converted 16th-century farmhouse located in Maidenhead, just a short distance from the town center and the River Thames. The property has received very good user ratings for cleanliness and overall experience, along with an excellent location rating.
The manor offers spacious grounds with 2 acres of garden and paddock, perfect for relaxing or enjoying the outdoors. The house provides a range of amenities, including free parking, free Wi-Fi, a swimming pool, a terrace, a garden, and a fully equipped kitchen.

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.

Stylish Home With Free Parking - 10 Mins To Legoland! - By Tempstay - Maidenhead
8.8 109 reviews
Maidenhead
10/17 – 10/24
$334/nighttotal: $2338 (7 )

Stylish Home With Free Parking - 10 Mins To Legoland! - By Tempstay

4 4
apartment , Windsor
This Windsor apartment is conveniently located near Legoland Windsor and Windsor Castle, making it an ideal choice for families and those wanting to explore the town's attractions. It consistently receives excellent ratings for location, cleanliness, and overall guest experience.
This 4-bedroom home provides ample space for larger groups. Enjoy the private garden, free parking, and a fully equipped kitchen with a washing machine.
Enchanting 1 Bed Cottage| Windsor By Tempstay - Maidenhead
Maidenhead
08/10 – 08/20
$256/nighttotal: $2560 (10 )

Enchanting 1 Bed Cottage| Windsor By Tempstay

1 1
apartment , Windsor
This newly renovated ground-floor apartment in Windsor City Centre offers a private garden and is located a short walk from Windsor Central Train Station, Windsor Castle, and the River Thames.
This one-bedroom, one-bathroom flat accommodates two guests and features a modern kitchen with a fridge, microwave, and dishwasher, a spacious lounge with WiFi and a Smart TV, and is conveniently located near Windsor Great Park and Long Walk.
Charming Victorian House W Parking River Walks - Pass The Keys - Maidenhead
9.4 176 reviews
Maidenhead
07/28 – 08/04
$687/nighttotal: $4809 (7 )

Charming Victorian House W Parking River Walks - Pass The Keys

5 6
house , Windsor
This grand Victorian home is located in Windsor, just a short walk from Windsor Castle and within easy reach of popular attractions like Legoland Windsor and Dorney Lake. The property consistently receives excellent ratings for location, cleanliness, and user experience.
This 5-bedroom home spans 1600 square feet and comfortably accommodates up to 10 guests. It features a fully equipped kitchen, a relaxing garden, free Wi-Fi, free parking, and amenities for disabled guests.
High Wycombe Apartments - Maidenhead
Maidenhead
07/28 – 08/04
$319/nighttotal: $2233 (7 )

High Wycombe Apartments

3 6
apartment , High Wycombe
This High Wycombe apartment is located 8.6 miles from Cliveden House and 14 miles from Dorney Lake, with Uxbridge Tube Station 15 miles away and London Heathrow Airport 20 miles away.
This pet-friendly lodging offers complimentary private parking, free WiFi, a 24-hour front desk, and fully equipped kitchens with a dishwasher, microwave, and oven, ideal for travelers seeking convenient access to local attractions and transport links.

Best Maidenhead vacation rentals with air conditioning

Page 256 By Ja'mo With King Bed And Free Parking - Maidenhead
Maidenhead
07/16 – 07/23
$247/nighttotal: $1729 (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 a short distance from Absolutely Ice - Slough Ice Arena and Eton College. The surrounding area offers easy access to popular attractions, shopping, and historical sites.
The apartment comfortably sleeps three guests and has a fully equipped kitchen, a Jacuzzi, and a dryer. You can enjoy modern amenities like a Smart TV, free WiFi, and air conditioning, along with a smoke-free environment.
Stylish 3 Bedroom Home Near Legoland Windsor Castle London Heathrow & Near River - Maidenhead
Maidenhead
10/10 – 10/17
$264/nighttotal: $1848 (7 )

Stylish 3 Bedroom Home Near Legoland Windsor Castle London Heathrow & Near River

3 4
apartment , Taplow
This Taplow condo is a short drive from Legoland Windsor Resort and Windsor Castle, with Heathrow Airport also nearby.
This 1350 sq ft residence accommodates up to six guests and features three bedrooms, one bathroom, a fully equipped kitchen with a dishwasher, air conditioning, a garden, a spa, and parking.
Willow Court Farm Studio West & Petting Farm, 8 Mins To Legoland & Windsor, 15 Mins To Lapland Uk - Maidenhead
9.6 123 reviews
Maidenhead
10/17 – 10/24
$302/nighttotal: $2114 (7 )

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

1 4
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.
40 M² House ∙ 4 Bedrooms ∙ 10 Guests - Maidenhead
Maidenhead
10/17 – 10/24
$400/nighttotal: $2800 (7 )

40 M² House ∙ 4 Bedrooms ∙ 10 Guests

4 4
house
This family-friendly house at 43 Badger Close borders Little Thicket National Trust and is a two-minute walk from Norreys Drive Station, offering a peaceful countryside escape near Maidenhead's amenities.
This 430-square-foot home accommodates up to 10 guests with four bedrooms, two bathrooms, a well-equipped kitchen, WiFi, air conditioning, and a private garden, located within a 15-minute walk of Norden Farm Centre for the Arts and Ockwells Park.
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