Book Luxury Holiday Lettings in Windsor

Award-winning homes from £98

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Age 13+

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Age 1 to 12

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Home spotlights in Windsor

Ebony & Ivory

Ebony & Ivory

  • 7 guests

  • 4 bedrooms

Highway, Maidenhead

This home located just outside of Maidenhead is certainly one of the more pared-back properties in our collection, but it's so well-executed that we felt compelled to include it. The ivory walls, shiny wooden floors and large windows combine together to make the interior feel bright and inviting.

The Saddler's Rooms

The Saddler's Rooms

  • 6 guests

  • 3 bedrooms

Hampshire, England

There's nothing quite like escaping to the country for a few days and this converted stable barn is a million miles away from the stresses of day-to-day life. Bright, open and immaculate in every way, it's a place to relax, take a deep breath of fresh, country air and enjoy the company of your loved ones.

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.

Eton Oasis

Eton Oasis

  • 6 guests

  • 2 bedrooms

Eton, Windsor

Footsteps from the shops, restaurants and cafes that line Eton High Street and a ten-minute walk from Windsor Castle, this cottage suits families, friends and couples alike. Inside, the design blends character with contemporary style, and it's packed with everything you'll need for a comfortable stay.


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

Explore the 5812 most perfect homes in our collection

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Most popular homes in Windsor

Escapade

Escapade

  • 10 guests

  • 5 bedrooms

Eton, Windsor

The Great British Retreat

The Great British Retreat

  • 18 guests

  • 9 bedrooms

Bray Civil Parish, Berkshire

The Whistler

The Whistler

  • 7 guests

  • 4 bedrooms

Old Windsor, Berkshire

Forgotten Fields

Forgotten Fields

  • 2 guests

  • 1 bedrooms

Tetsworth, Thame

Masterpiece

Masterpiece

  • 2 guests

  • 1 bedrooms

Woodstock, Oxfordshire

One of England's Watery Gems

One of England's Watery Gems

  • 10 guests

  • 5 bedrooms

Wraysbury, England

The Guildford Gully

The Guildford Gully

  • 12 guests

  • 6 bedrooms

Windsor, Berkshire

Grace & Light

Grace & Light

  • 4 guests

  • 2 bedrooms

East Molesey, England

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Frequently asked questions

Explore our selection of the finest luxury Holiday Lettings 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 Lettings for your trip.

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