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House vacation rentals in Windsor and Maidenhead

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Top-rated house rentals in Windsor and Maidenhead

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Guest favorite
The exterior of the property is displayed, featuring a blend of traditional and modern architecture. A courtyard with landscaped greenery is visible at the center, surrounded by the building's stone facade. Tall trees and blue skies add a serene backdrop to the scene.
Home in Englefield Green
4.87 out of 5 average rating, 173 reviews

Charming 5* Hse Near Windsor Castle, Ascot, London

This Grade 11 listed Mews property was built in 1872 and offers contemporary, luxurious living space. Luxurious king size beds, a beautiful bathroom, abundant art and character; the property looks onto an ancient courtyard with fountain, secure behind private gates with parking. The location is exceptional. Windsor Great Park is a 10 min stroll away, and Windsor is 3 miles away, Wentworth Golf Club and Ascot are all within 6 miles. Central London is 35 minutes by train. Heathrow is 6 miles away.

Top guest favorite
The welcoming living area features a spacious gray sofa adorned with colorful cushions. A patterned area rug lies beneath the seating, which is accompanied by a stylish dining table. An open entryway leads to the kitchen, with abundant natural light streaming in from the garden.
Home in Marlow
5 out of 5 average rating, 115 reviews

Magical Marlow town centre

Wing Cottage is a charming period terraced cottage with log burner in the heart of Marlow. It has been stylishly refurbished and has its own secluded courtyard garden. 5 minutes walk from High St shops with Everyman Cinema, Tom Kerridge’s Michelin* Hand &Flowers & The Coach, plus Marlow Ivy Garden, Côte Brasserie, Piccolino, The Compleat Angler and several historic pubs. The Park and Thames Path river walk are 10 minutes walk. Nearby bus stops serve neighbouring Henley-on-Thames (8 miles away).

Guest favorite
The exterior of the Coach House displays a combination of traditional brickwork and modern design. Black doors are framed by large windows, while a small stone table with chairs is positioned by the entrance. Decorative plants add a touch of greenery to the inviting facade.
Home in Windsor and Maidenhead
4.95 out of 5 average rating, 263 reviews

Historic building in the centre of Windsor.

Beautifully renovated 1850's Coach House. This is part of a building that housed Queen Victoria's Equerries at Windsor Castle. Based in central Windsor with private parking, the property is an ideal place for a staycation. Mess about on the river (boating, paddle boarding, swimming) or visit the many beauty spots in the area. Legoland, Windsor Great Park, Windsor Castle and Swinley mountain bike trails are all within easy reach. A unique property that we hope that you will love as much as us.

Top guest favorite
The serene landscape captures a glowing sunset over the River Thames, with reflections shimmering on the water. A grassy area leads to the river, framed by trees and plant life, creating a peaceful backdrop for a tranquil evening.
Home in Dorchester
4.98 out of 5 average rating, 390 reviews

Secluded River Thames Lodge with Spectacular Views

Herons is totally unique, a beautiful detached lodge situated on the banks of the River Thames. Beautiful interiors and the views are simply wonderful from sunrise to sunset. Herons is the perfect place to unwind and relax, just sit and watch the wildlife and the boats milling along the river. Nearby are the Thames Market towns of Wallingford, Henley and Abingdon and the beautiful surrounding countryside.The historic city of Oxford is only 8 miles away and Bicester Village is a 30 minute drive.

Guest favorite
A spacious lounge area features a comfortable sofa draped with a green throw and adorned with colorful cushions. A sleek side table stands nearby. Light wood flooring extends to a dining area, which includes a table surrounded by green chairs. A spiral staircase leads to the upper level.
Home in Berkshire
4.95 out of 5 average rating, 104 reviews

Windsor Cottage: Traditional English Charm

Only 20 minutes from London Heathrow Airport and ideally located in one of the most central terraces in Windsor, our cosy cottage is full of character and charm, with all the modern conveniences you'd expect. Perfect for a romantic get-away or a family sight-seeing trip. Windsor Cottage is an 1890's two bedroom terrace house that comfortably sleeps a family or 4 (+ travel cot). A home away from home, you will find all of the luxury and convenience expected of a traditional English cottage.

Superhost
The living room features a combination of comfortable seating, including a plush gray sofa and a vibrant yellow armchair. A smart TV is placed on a modern media console, while a patterned area rug adds warmth to the space. Natural light enters through large windows, enhancing the inviting atmosphere.
Home in Colnbrook
4.84 out of 5 average rating, 110 reviews

Shal Home @ Heathrow -pick & Drop + Parking

Book this family &bussiness friendly,well connected to London and only 10 mins away from Heathrow airport. You are welcome to bring your car as free parking available on premises. Pick and drop to airport is also available on request. Public transport is only couple of mins walk away. Elizabeth line to central London from Langley station, which is 2 miles away. 20 mins by bus to Langley station Attractions Windsor Castle Legoland Windsor resort Thorpe park Chessington world of adventure

Top guest favorite
A bright living area features a spacious gray sofa with red accent pillows and a large checkered ottoman. Skylights provide natural light, while framed art decorates the walls. A dining table is situated nearby, with sliding doors leading to an outdoor terrace.
Home in Pangbourne
5 out of 5 average rating, 233 reviews

A Perfect Pad in Pangbourne!

The house was 'created' in 2020 having originally been part of the village pub - its now part of a redeveloped property which also includes the owners home and a fabulous cafe called Artichoke Cafe The property is right in the heart of the picturesque riverside village of Pangbourne with its fabulous specialist shops, cafes, restaurants and pubs. Yet only ten minutes walk gets you to the countryside! The village also boasts a mainline station with direct trains to London Paddington.

Superhost
The historic brick exterior of the building is adorned with gothic-style windows, framed by lush greenery. A pathway leads through the landscaped gardens, where trees and shrubs offer a serene atmosphere. The architecture reflects the character of a Grade II listed structure.
Home in Windsor
4.92 out of 5 average rating, 114 reviews

The Truly Incredible Windsor Home, Free Parking

Welcome to your stay at this incredible and unique Grade II listed building- a stunning 3 bedroom house. Absolutely NO Parties and NO Events. I live close by and guests will be asked to leave immediately. No loud sounds after 10pm. We have to be very respectful of our neighbours. Walk to town in around 20 minutes where you will be able to visit all of the shops and sights. Alternatively hop in the car and drive to Legoland in around 5 minutes or Ascot Racecourse in just over 10.

Top guest favorite
The exterior of the modern annexe is showcased, featuring large glass doors that allow natural light to fill the interior. A spacious balcony is visible above, bordered by glass, and wooden furniture is arranged on the terrace, ideal for outdoor relaxation.
Home in Tetsworth
5 out of 5 average rating, 349 reviews

Luxury self-contained Annexe with balcony Jacuzzi

Luxury self-contained annexe on the edge of the Chilterns, situated in the peaceful countryside which can be enjoyed from the hot tub, yet only 5 mins to the M40, 15 mins to Oxford Park & Ride & 15 mins to the station with trains to London taking 45 mins. It is the perfect place to relax with cosy lounge, wood burning stove, bespoke kitchen & underfloor heating. Upstairs features a super-king sized bed, seating area, luxury wet-room with underfloor heating, balcony and Jacuzzi.

Guest favorite
A spacious terrace is furnished with wicker seating and a wooden table, providing a comfortable area for relaxation. The serene view of the river Thames is framed by lush greenery and a bright blue sky, creating a peaceful outdoor setting.
Home in Wraysbury
4.96 out of 5 average rating, 137 reviews

River Thames near Windsor, Heathrow & London

Our home sits on the beautiful river Thames in Wraysbury near Windsor. The river runs past the end of the garden. There is a large west facing terrace, from the master bedroom. There is a large living room, kitchen and dinning room. 3 double bedrooms. There's parking for 2 cars in the garden. Windsor, Windsor castle and Lego land are about 20mins away my car. From Wraysbury station you can get into London Waterloo in 42mins. Heathrow is only 15mins drive away.

Guest favorite
An open-plan kitchen and dining area features large skylights allowing ample natural light. A modern kitchen with sleek cabinetry is complemented by a spacious dining table surrounded by benches. Decorative plants and a minimalist decor enhance the inviting atmosphere of the space.
Home in Windsor and Maidenhead
4.92 out of 5 average rating, 100 reviews

Elegant 5-Bed Home in Central Windsor + Parking

Stay in comfort at Clarence House, a beautifully presented 5-bedroom, 2-bathroom home in the heart of Windsor. Perfect for families or business travellers. The house features driveway parking, a large private garden, fully equipped kitchen, and free Wi-Fi. Just a 15-minute walk to Windsor train station (40 mins to London) and a short stroll to Windsor Castle, shops, cafés, and the River Thames. Enjoy the best of Berkshire from this stylish and convenient retreat.

Top guest favorite
A red-brick exterior features two separate white doors, leading into the private annexe. Solar panels are installed on the roof, and the surrounding area includes a paved patio with a smooth stone surface, complemented by greenery in the background.
Home in Old Windsor
4.94 out of 5 average rating, 130 reviews

Private annexe in Old Windsor.

A private double bedroom annexe, with its own entrance, separated from main house. Private bathroom and full use of the gymnasium and lovely garden. (which includes a small wood area). The house is situated right on the doorstep of Windsor Great Park, in Old Windsor. Windsor town centre is 3 miles away and we are close to Heathrow and the M25 and M4.

Popular amenities for Windsor and Maidenhead house rentals

When is the best time to visit Windsor and Maidenhead?

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Avg. priceG$33,254 GYDG$33,672 GYDG$33,881 GYDG$37,437 GYDG$39,319 GYDG$43,502 GYDG$46,221 GYDG$44,757 GYDG$40,783 GYDG$36,809 GYDG$35,554 GYDG$39,110 GYD
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Quick stats about house rentals in Windsor and Maidenhead

  • Total vacation rentals

    Explore 1,070 vacation rentals in Windsor and Maidenhead

  • Verified guest reviews

    Over 25,780 verified reviews to help you choose

  • Family-friendly vacation rentals

    640 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 270 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    410 properties have a dedicated workspace

  • Wi-Fi availability

    1,040 of Windsor and Maidenhead vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Windsor and Maidenhead rentals

  • 4.8 Average rating

    Windsor and Maidenhead stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Windsor and Maidenhead's top spots, include Ascot Racecourse, Virginia Water Lake, and Odeon Maidenhead

Destinations to explore