Book Luxury Vacation Rentals for May in Windsor

We selected the 5762 homes worth renting in this location

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Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Home spotlights in Windsor

Gather & See

Gather & See

  • 10 guests

  • 5 bedrooms

Windsor, Berkshire

This home is a great option for groups looking for a centrally-located stay in Windsor. By day, you can enjoy all that the city has to offer on foot – Windsor Castle is a short walk away and you’ll find the river is within easy reach.

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.

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.

Wraysbury Dream

Wraysbury Dream

  • 10 guests

  • 4 bedrooms

Wraysbury, England

Cosy and comfortable, this family home has everything you need for a stay in the Berkshire countryside. We love the character here, especially the kitchen's exposed beams and stone walls.


We selected the top 3% holiday homes in Windsor Vacation Rentals for May

Explore the 5762 most perfect homes in our collection

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Most popular homes in Windsor

Surrey Hills Manor

Surrey Hills Manor

  • 16 guests

  • 8 bedrooms

Tadworth, Surrey

The Eclectic Hidden Cottage

The Eclectic Hidden Cottage

  • 5 guests

  • 3 bedrooms

Esher, Surrey

Pink Slice

Pink Slice

  • 6 guests

  • 2 bedrooms

Windsor, Berkshire

The Windsor Lookout

The Windsor Lookout

  • 6 guests

  • 3 bedrooms

Windsor, Berkshire

The Great British Retreat

The Great British Retreat

  • 18 guests

  • 9 bedrooms

Bray Civil Parish, Berkshire

Skindles

Skindles

  • 5 guests

  • 2 bedrooms

Maidenhead, Berkshire

Mister Modern

Mister Modern

  • 2 guests

  • 1 bedrooms

Dunstable, Central Bedfordshire

Forgotten Fields

Forgotten Fields

  • 2 guests

  • 1 bedrooms

Tetsworth, Thame

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Check upcoming rates & availability for Windsor Vacation Rentals for May


Frequently asked questions

Discover our exclusive collection of the finest Vacation Rentals for May that Windsor has to offer, and mark the month with an unforgettable trip. At Plum Guide, we carefully select only the very best homes around, so you know that every rental is one to be proud of. Each home in our range comes fully furnished, with a well-equipped kitchen, all linen, and essential toiletries included. Our meticulous testing process ensures that no stone is left unturned, with everything from shower pressure and Wifi speed to a home's design aesthetic being thoroughly tested. Book a luxury Holiday Rental for May in Windsor today, and see what all the fuss is about. If you need any guidance, call on our experts, ready night and day to help you find your ideal home.

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