Book Luxury Holiday Lettings in Maidenhead

Award-winning homes from £98

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Home spotlights in Maidenhead

River & Roses

River & Roses

  • 6 guests

  • 3 bedrooms

Henley-on-Thames, England

We love the views from the large kitchen of this home’s courtyard garden with its tranquil water feature. Ideal for families or friends, there’s a snug complete with comfy sofas, woollen throws and a log burner for the cooler nights.

The Lark Ascending

The Lark Ascending

  • 12 guests

  • 6 bedrooms

Reading, Oxfordshire

Picture a quiet village in the Chiltern Hills, with a gorgeous redbrick house, clematis scaling its exterior and a bloom of white hydrangea to greet you upon entry. Fortunately, it’s not too good to be true, you’ll find this idyllic escape on the cusp of Sonning Common.

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.

Sunsets & Swan Feathers

Sunsets & Swan Feathers

  • 7 guests

  • 4 bedrooms

Eton, Windsor

Cloaked in soothing tones, this understated Eton home is the perfect setting for a relaxing staycation, situated within easy reach of Windsor’s most popular attractions. Whether you’re here for the town’s namesake castle or simply to escape the hustle and bustle of city life, you can’t do much better than this gorgeous, family abode which comes complete with its own private garden, perfect for letting little ones and furry friends roam free while you savour a well-deserved cuppa in the fresh air.


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

Explore the 5948 most perfect homes in our collection

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Most popular homes in Maidenhead

The Belgian Ambassador

The Belgian Ambassador

  • 8 guests

  • 4 bedrooms

Bray Civil Parish, Berkshire

Pink Slice

Pink Slice

  • 6 guests

  • 2 bedrooms

Windsor, Berkshire

A Royal Regatta

A Royal Regatta

  • 5 guests

  • 2 bedrooms

Henley-on-Thames, England

The Coxswain

The Coxswain

  • 14 guests

  • 6 bedrooms

Henley-on-Thames, England

Eton Oasis

Eton Oasis

  • 6 guests

  • 2 bedrooms

Eton, Windsor

One of England's Watery Gems

One of England's Watery Gems

  • 10 guests

  • 5 bedrooms

Wraysbury, England

Britannia Jewel

Britannia Jewel

  • 5 guests

  • 3 bedrooms

Windsor, Berkshire

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 Lettings 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 Lettings for your trip.

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