Book Luxury Holiday Rentals in Maidenhead

Award-winning homes from £98

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Home spotlights in Maidenhead

The Riverside Refuge

The Riverside Refuge

  • 14 guests

  • 5 bedrooms

Henley-on-Thames, England

This characterful home feels as if it’s straight out of a period drama, with exposed beams and shopfront windows. That’s not to say it’s old-fashioned — the interiors are bright and airy, more country chic than dingy pub.

The Windsor Crown

The Windsor Crown

  • 5 guests

  • 3 bedrooms

Old Windsor, England

Located just a short drive from the centre of Window and its famous castle, this two-storey suburban spot is a homely base for excursions. The bedrooms are on the plain side, but the large garden is great for kids – let them tire themselves out as you enjoy alfresco dining on the terrace.

Fond Memories

Fond Memories

  • 10 guests

  • 5 bedrooms

Windsor, Berkshire

This Windsor homestay might only be fifteen minutes from the nearest train station, but convenience is far from the only thing this luxury property has to offer. Large windows flood the interior with natural light, highlighting soft textures and thoughtful accents that make you feel at home the second you step over the threshold.

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 Maidenhead Holiday Rentals

Explore the 6210 most perfect homes in our collection

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Most popular homes in Maidenhead

Skindles

Skindles

  • 5 guests

  • 2 bedrooms

Maidenhead, Berkshire

A Royal Regatta

A Royal Regatta

  • 5 guests

  • 2 bedrooms

Henley-on-Thames, England

Good Mews

Good Mews

  • 4 guests

  • 2 bedrooms

Henley-on-Thames, England

Wraysbury Dream

Wraysbury Dream

  • 10 guests

  • 4 bedrooms

Wraysbury, England

The Lark Ascending

The Lark Ascending

  • 12 guests

  • 6 bedrooms

Reading, Oxfordshire

River Rest

River Rest

  • 2 guests

  • 1 bedrooms

Marlow, England

A Day at the Regatta

A Day at the Regatta

  • 14 guests

  • 4 bedrooms

Dorney, Buckinghamshire

River & Roses

River & Roses

  • 6 guests

  • 3 bedrooms

Henley-on-Thames, England

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Frequently asked questions

Explore our selection of the finest luxury Holiday Rentals for your next getaway in 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 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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