Book Luxury Holiday Rentals in Windsor and Maidenhead

Award-winning homes from £98

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Home spotlights in Windsor and Maidenhead

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.

Painted White

Painted White

  • 5 guests

  • 3 bedrooms

Esher, Surrey

Tucked into the picturesque village of Esher, this semi-detached home is an idyllic spot for a relaxed stay. While you’ll share the garden with the adjoining home, there’s plenty of space for alfresco meals when the sun is shining.

Eton Rifles

Eton Rifles

  • 5 guests

  • 2 bedrooms

Slough, Berkshire

This apartment, a ten-minute walk from the heart of Slough, offers contemporary comfort with fuss-free design to make short sojourns or longer stays a breeze. A soothing palette of greys and sage is a treat to come home to after day excursions or quick trips into town.

The Windsor Lookout

The Windsor Lookout

  • 6 guests

  • 3 bedrooms

Windsor, Berkshire

Minutes away from central Windsor, this riverside apartment is in the perfect spot to discover the many shopping and restaurant areas on your doorstep. Although it isn’t the biggest apartment, and it being on the second floor may be difficult for those with limited mobility to access, multiple openings to the breezy balcony opens up the space when socialising with family or friends.


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

Explore the 6782 most perfect homes in our collection

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Most popular homes in Windsor and Maidenhead

Britannia Jewel

Britannia Jewel

  • 5 guests

  • 3 bedrooms

Windsor, Berkshire

Winkfield Woods

Winkfield Woods

  • 3 guests

  • 1 bedrooms

Cranbourne, Windsor

Skindles

Skindles

  • 5 guests

  • 2 bedrooms

Maidenhead, Berkshire

Teak On White

Teak On White

  • 8 guests

  • 4 bedrooms

Reading, Berkshire

Grace & Light

Grace & Light

  • 4 guests

  • 2 bedrooms

East Molesey, England

The Windsor Crown

The Windsor Crown

  • 5 guests

  • 3 bedrooms

Old Windsor, England

A Day at the Regatta

A Day at the Regatta

  • 14 guests

  • 4 bedrooms

Dorney, Buckinghamshire

A King's Retreat

A King's Retreat

  • 8 guests

  • 4 bedrooms

Sunninghill and Ascot, Berkshire

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in Windsor and Maidenhead. 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 and Maidenhead 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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