Book Luxury Holiday Rentals in Windsor

Award-winning homes from £98

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Home spotlights in Windsor

A Day at the Regatta

A Day at the Regatta

  • 14 guests

  • 4 bedrooms

Dorney, Buckinghamshire

Part of the historic Estate of Dorney Court, this timber-framed house dates back to the sixteenth century and is a magical blend of heritage and modernity. The former great hall is emblematic of this.

Green on My Mind

Green on My Mind

  • 10 guests

  • 5 bedrooms

Shere, Guildford

Just a five-minute walk from the picture-perfect village of Shere in the Surrey Hills, this place is a much-loved family home. Set in five acres of private grounds, with views across the rolling hills, it's bound to be a hit with lovers of the great outdoors, with excellent hiking and cycling routes from your door.

Joy & Ease

Joy & Ease

  • 4 guests

  • 2 bedrooms

Warfield, Berkshire

Placing you right in the heart of Warfield, this home provides a practical yet cosy space from which to explore the Berkshire countryside. There are forest walks and cycle trails within easy reach, while it’s just a five-minute drive to the shops and restaurants of the Lexicon – a great option for family entertainment.

Britannia Jewel

Britannia Jewel

  • 5 guests

  • 3 bedrooms

Windsor, Berkshire

Sitting on a quiet residential street in central Windsor, this beautiful upper maisonette offers a warm and welcoming base for those looking to experience the town’s rich and royal history, as well as the delights of nearby Eton, Ascot and Legoland. Laid out over three floors, you’ll find plenty of space to socialise as well as opportunities to steal yourself await for some relaxing privacy.


We selected the top 3% holiday homes in Windsor Holiday Rentals

Explore the 5594 most perfect homes in our collection

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Most popular homes in Windsor

Royal Next Door

Royal Next Door

  • 6 guests

  • 3 bedrooms

Windsor, Berkshire

Secret Garden Games

Secret Garden Games

  • 8 guests

  • 5 bedrooms

Burnham, Slough

Wraysbury Dream

Wraysbury Dream

  • 10 guests

  • 4 bedrooms

Wraysbury, England

Forgotten Fields

Forgotten Fields

  • 2 guests

  • 1 bedrooms

Tetsworth, Thame

The Boat Race

The Boat Race

  • 4 guests

  • 2 bedrooms

Henley-on-Thames, England

Pink Slice

Pink Slice

  • 6 guests

  • 2 bedrooms

Windsor, Berkshire

Sunsets & Swan Feathers

Sunsets & Swan Feathers

  • 7 guests

  • 4 bedrooms

Eton, Windsor

River Rest

River Rest

  • 2 guests

  • 1 bedrooms

Marlow, England

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Windsor. The homes in Plum Guide's collection come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Each home is professionally vetted and carefully handpicked, with both measurable and soft 'feel' elements thoroughly tested to ensure the highest quality. Book today and enjoy a short or extended stay in one of the best homes that Windsor has to offer. Our friendly experts are also on hand 24/7, should you need any help finding the perfect Holiday Rentals for your trip.

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