Book Luxury Holiday Rentals in Maidenhead

Award-winning homes from £98

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Home spotlights in Maidenhead

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.

Pink Slice

Pink Slice

  • 6 guests

  • 2 bedrooms

Windsor, Berkshire

A fifteen-minute stroll from the shop-lined High Street, you'll find Windsor Castle beyond – a must-see fortress for royal family fans. Fancy afternoon tea at a nearby racecourse?

Life in the Woods

Life in the Woods

  • 6 guests

  • 2 bedrooms

Harpsden, Henley-on-Thames

This charming wood-clad barn is tucked away down a tranquil private lane surrounded by idyllic Oxfordshire countryside. Inside, high vaulted ceilings and a log-burning fire bring the wow factor, and the green vistas seen through the floor-to-ceiling windows are a delight, whatever the season.

The Belgian Ambassador

The Belgian Ambassador

  • 8 guests

  • 4 bedrooms

Bray Civil Parish, Berkshire

Built back in 1861, this home was originally a vicarage to an adjacent church, which was demolished in the 1960s — there's a still small cemetery at the front of the property. Things have certainly moved on since the middle of the nineteenth century and the interior is a triumph of modern design.


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

Explore the 6598 most perfect homes in our collection

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Most popular homes in Maidenhead

Skindles

Skindles

  • 5 guests

  • 2 bedrooms

Maidenhead, England

Good Mews

Good Mews

  • 4 guests

  • 2 bedrooms

Henley-on-Thames, England

River & Roses

River & Roses

  • 6 guests

  • 3 bedrooms

Henley-on-Thames, England

A Windsor Welcome

A Windsor Welcome

  • 8 guests

  • 5 bedrooms

Datchet, Slough

Rural Yet Refined

Rural Yet Refined

  • 8 guests

  • 4 bedrooms

Binfield Heath, Henley-on-Thames

Escapade

Escapade

  • 10 guests

  • 5 bedrooms

Eton, Windsor

A Day at the Regatta

A Day at the Regatta

  • 14 guests

  • 4 bedrooms

Dorney, Buckinghamshire

The King's Repose

The King's Repose

  • 4 guests

  • 2 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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