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Maidenhead vacation rentals
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Best Vacation rentals and Airbnb offers in Maidenhead

Discover Central Vacation Rentals in Maidenhead

From vibrant downtown areas to historic streets, these Maidenhead vacation rentals put you close to everything worth seeing.

The Green Views Apartment Contractors, Families, Travels - Maidenhead
9.7 26 reviews

The Green Views Apartment Contractors, Families, Travels

apartment, Maidenhead
This Maidenhead apartment is located near the town center, just a short drive from Cliveden House, Windsor Castle, and Legoland Windsor. It boasts excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay. The apartment features a cozy bedroom and a fully equipped kitchen, offering a convenient and relaxing experience. Guests can enjoy amenities like free Wi-Fi, a washing machine, and a peaceful atmosphere, making it an ideal choice for exploring Maidenhead and its surrounding attractions.
Maidenhead - Gated Parking Balcony - Maidenhead
9.0 8 reviews

Maidenhead - Gated Parking Balcony

apartment, Maidenhead
This Maidenhead apartment rental is conveniently located near Legoland Windsor (8.3 miles), Windsor Castle (9.1 miles), and LaplandUK (10 miles), offering easy access to popular attractions.
This 640-square-foot (approximately 60-square-meter) two-bedroom, one-bathroom unit features free Wi-Fi, free gated parking, a fully equipped kitchen with a microwave and refrigerator, and in-unit laundry facilities; it comfortably accommodates families or groups of up to four.
Stunning 2br Flat With Balcony - Maidenhead
10 2 reviews

Stunning 2br Flat With Balcony

apartment, London
This 2-bedroom flat in Maidenhead is located 4.3 miles from Dorney Lake and 7.1 miles from Windsor Castle, offering convenient access to popular attractions.
This 710 sq ft apartment accommodates up to 5 guests with 2 bathrooms, a fully equipped kitchen featuring a dishwasher and microwave, and complimentary WiFi, plus a private balcony.
Near Town Centre, Big Patio, Free Parking Sleeps 8 - Maidenhead
10 24 reviews

Near Town Centre, Big Patio, Free Parking Sleeps 8

apartment
This Berkshire house rental is conveniently located in a quiet area, a short drive from Waitrose (2 minutes) and Lidl (5 minutes), and within easy reach of Windsor town center (5 minutes), Royal Windsor Racecourse (12 minutes), and Legoland (18 minutes).
This four-bedroom home sleeps eight guests comfortably, offering a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus free Wi-Fi, a smart TV, and private parking; enjoy a large patio perfect for outdoor dining.

Best Maidenhead vacation rentals with air conditioning

2 Bed Penthouse - Castle Views - By Tempstay - Maidenhead
9.6 5 reviews

2 Bed Penthouse - Castle Views - By Tempstay

apartment, Berkshire
This Clewer East apartment rental is conveniently located in Berkshire, England, within two 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, in-unit laundry, and a private balcony; nearby attractions include Windsor & Eton Central and Riverside train stations, easily accessible by foot.
Private Garden Annex With Own Entrance - Maidenhead
9.9 89 reviews

Private Garden Annex With Own Entrance

cabin
This Berkshire cottage is conveniently located near Holyport, offering easy access to the M4 motorway and short drives to Windsor Castle, Ascot Racecourse, Marlow, and Henley-on-Thames.
The one-bedroom, one-bathroom unit features an open-plan kitchen, living, and dining area, sleeping up to two guests and including a fully equipped kitchenette, TV, and electric fire.
2br Penthouse |Cinema Room|parking - By Tempstay - Maidenhead
10 1 review

2br Penthouse |Cinema Room|parking - By Tempstay

apartment, Berkshire
This Clewer East apartment rental is conveniently located less than 2 miles from Windsor Castle and LEGOLAND Windsor Resort, and about 1 mile from the Thames River.
The two-bedroom, three-bathroom unit sleeps four guests and includes a fully equipped kitchen, private balcony, in-unit laundry, and parking; nearby attractions include Windsor & Eton Central and Riverside train stations.
Families & Friends | Parking & Ev | Station Nearby - Maidenhead
10 74 reviews

Families & Friends | Parking & Ev | Station Nearby

apartment
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.

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.

Popular destinations

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
9.0 190 reviews

Hampden Apartments - The Anne

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.
Charming Windsor Cottage, Incredible Location, Castle Doorstep - Maidenhead
8.5 57 reviews

Charming Windsor Cottage, Incredible Location, Castle Doorstep

house, Windsor
This Windsor cottage boasts an exceptional location, a 4-minute walk from Windsor Castle and 2.5 miles from Legoland Windsor.
This two-bedroom house sleeps up to 11 guests and features a fully equipped kitchen, free Wi-Fi, free parking, and a terrace—perfect for families or groups exploring Windsor's attractions.
Modern 2 Bed Apartment - Allocated Parking - By Tempstay - Maidenhead
9.2 5 reviews

Modern 2 Bed Apartment - Allocated Parking - By Tempstay

apartment, Windsor
This Windsor apartment rental is located a short drive from Windsor Castle (1.1 miles) and Legoland Windsor (1.6 miles), offering easy access to major attractions.
The 1,080-square-foot unit features two bedrooms, two bathrooms, a fully equipped kitchen with a dishwasher, and a private balcony and garden, comfortably accommodating up to five guests.
Maidenhead Fabulous Stylish Two Bedroom Penthouse - Maidenhead
No reviews

Maidenhead Fabulous Stylish Two Bedroom Penthouse

apartment, Maidenhead
This top-floor condo in Maidenhead is located a five-minute walk from the train station and town center, offering convenient road access to the M4, M25, and M40 motorways, and is within reach of the Thames River.
This pet-friendly rental spans 860 square feet, featuring two bedrooms and two bathrooms to accommodate up to four guests, with a kitchen equipped with a fridge, microwave, and dishwasher, plus a private balcony overlooking communal gardens and an adjacent golf course.

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.

Central Windsor Stunning 4 Bedroom Spacious Modern House - Maidenhead
9.3 27 reviews

Central Windsor Stunning 4 Bedroom Spacious Modern House

house, Windsor
This modern home is located in Central Windsor, just a short distance from both Legoland Windsor and Windsor Castle, making it an ideal base for exploring the area. The house has received excellent ratings for location, cleanliness, and overall user experience.
The 4-bedroom house offers 1780 square feet of space, perfect for families or groups. Guests can enjoy a private garden, barbecue facilities, and a dedicated outdoor dining area, as well as amenities like a fully equipped kitchen, free Wi-Fi, and a washing machine.
Windsor/ascot/bracknell Beautiful Barn - Maidenhead
9.2 212 reviews

Windsor/ascot/bracknell Beautiful Barn

farm
This vacation home is located just 2.2 miles from Bracknell and Wokingham College and within 6 miles of both LEGOLAND® Windsor and Lapland UK, making it a convenient base for exploring the surrounding area. The property has earned excellent ratings for cleanliness, location, and overall user experience.
The home features one bedroom and one bathroom, accommodating up to two guests. Amenities include a fully equipped kitchen, a washing machine, WiFi, a TV, barbecue grills, and a garden, providing everything you need for a comfortable stay.
3-bed Bungalow Near Elizabeth Line, Parking - Maidenhead
9.0 2 reviews

3-bed Bungalow Near Elizabeth Line, Parking

house, Burnham
This recently renovated 3-bedroom bungalow in Burnham is located 3.6 miles from Dorney Lake and Cliveden House, and 12 miles from London Heathrow Airport.
This 970 square foot vacation home accommodates up to 11 guests and features a fully equipped kitchen, free WiFi, on-site parking, and a garden with outdoor seating.
St Georges House, Premium 3 Bed Home Slough, Legoland, Windsor - Maidenhead
9.0 79 reviews

St Georges House, Premium 3 Bed Home Slough, Legoland, Windsor

house, Slough
This luxurious Victorian home is located in Slough, just a short drive from Legoland Windsor and Dorney Lake, making it a perfect base for exploring the area. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This spacious home has three bedrooms and can accommodate up to 10 guests. The property offers a range of amenities, including a terrace, garden, spa, fitness center, tennis court, and parking, ensuring a comfortable and enjoyable stay.

Best Maidenhead vacation rentals with parking

Nr Windsor- Unique Cottage Stay For Upto 14 Guests - Maidenhead
9.4 3 reviews

Nr Windsor- Unique Cottage Stay For Upto 14 Guests

cottage, Dorney
Bright & Spacious 3-bed, 2-bath Home In Graylands Close - Maidenhead
9.5 2 reviews

Bright & Spacious 3-bed, 2-bath Home In Graylands Close

house, Slough
Stylish 1 Bed & Parking-ideal For Corporate Stays - By Tempstay - Maidenhead
8.6 14 reviews

Stylish 1 Bed & Parking-ideal For Corporate Stays - By Tempstay

apartment, Slough
Acorn Lodge Windsor - Pass The Keys - Maidenhead
10 1 review

Acorn Lodge Windsor - Pass The Keys

house, Winkfield

Find the Best Luxury Vacation Rentals in Maidenhead

Elevate your stay in a luxury vacation rental or Airbnb in Maidenhead, featuring high-end finishes and a prime location.

Burnham / Slough Spacious Six Bedroom House - Maidenhead
No reviews

Burnham / Slough Spacious Six Bedroom House

chalet, Burnham

Discover Pet-Friendly Vacation Rentals in Maidenhead

Experience a pet-friendly stay in Maidenhead with vacation rentals located steps away from city dog parks and walking trails.

Boutique Executive Apartment  Windsor,  Free Parking, Garden,  Sleeps Up 4. - Maidenhead
No reviews

Boutique Executive Apartment Windsor, Free Parking, Garden, Sleeps Up 4.

apartment, Slough
Stylish 2-bed Maisonette Free Parking Small Pool Table - Maidenhead
No reviews

Stylish 2-bed Maisonette Free Parking Small Pool Table

apartment, Farnham Royal
The Old Estate Office - Enchanting, Stylish Garden Cottage, Peaceful & Quiet - Maidenhead
9.6 168 reviews

The Old Estate Office - Enchanting, Stylish Garden Cottage, Peaceful & Quiet

house, Hurley
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

Top-Rated Vacation Rentals with a Pool in Maidenhead

Choose a Maidenhead rental with a pool for a refreshing swim right in the heart of the city.

Romantic 3beds Yacht Escape On Thames - Maidenhead
No reviews

Romantic 3beds Yacht Escape On Thames

apartment, Staines
Riverside Retreat| Sauna & Pool - By Tempstay - Maidenhead
No reviews

Riverside Retreat| Sauna & Pool - By Tempstay

apartment, Berkshire
Period Luxury Converted Barn Windsor/maidenhead - Perfect For Family Groups - Maidenhead
9.3 3 reviews

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

house, Taplow
Forest Getaway - Countryside Retreat Near Windsor - Maidenhead
10 2 reviews

Forest Getaway - Countryside Retreat Near Windsor

house, Hedgerley

Top Vacation Rentals with a Hot Tub in Maidenhead

Unwind at the end of a busy city day with a private hot tub at these hand-selected vacation rentals in Maidenhead.

Design-led- 2xsuper-king Beds- Ensuites- W Parking - Maidenhead
10 4 reviews

Design-led- 2xsuper-king Beds- Ensuites- W Parking

cottage, Eton
Wellness Escape By River, Sauna, Heated Pool, Hot Tub - Maidenhead
8.0 1 review

Wellness Escape By River, Sauna, Heated Pool, Hot Tub

house, Windsor
4 Bed In Bray Oc-b32610 - Maidenhead
No reviews

4 Bed In Bray Oc-b32610

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

4 Bed In Bray (Oc-b32610)

cottage, Bray
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