Book Luxury Winter Rentals in Sunninghill and Ascot

We selected the 5962 homes worth renting in this location

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Home spotlights in Sunninghill and Ascot

A King's Retreat

A King's Retreat

  • 8 guests

  • 4 bedrooms

Sunninghill and Ascot, Berkshire

This family home caught our eye not just because it's well-located for exploring nearby Windsor – we also like that it's got more than enough space for everyone in your group. The annex is ideal if you've got teens who might want time to themselves, while younger kids will love the bunk beds in the main house.

One of England's Watery Gems

One of England's Watery Gems

  • 10 guests

  • 5 bedrooms

Wraysbury, England

Nestled between two islands on the picturesque banks of the River Thames – this beautiful thatched Edwardian home built in 1903, under a fifteen-minute drive from Windsor, is the perfect riverside retreat. Watch the boats, ducks and swans on the river go by from your own private heated pool.

The Queen's Lodge

The Queen's Lodge

  • 4 guests

  • 2 bedrooms

Windsor, Berkshire

If you’ve ever wondered what it would be like to live next door to a member of the royal family, this place might have the answers. Situated just a few metres from iconic Windsor Castle, this simple but stylish apartment is a great base for those looking to get up close and personal with British royalty, tucked just round the corner from the late Queen’s historic weekend home.

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 Sunninghill and Ascot Vacation Rentals for Winter

Explore the 5962 most perfect homes in our collection

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Most popular homes in Sunninghill and Ascot

Britannia Jewel

Britannia Jewel

  • 5 guests

  • 3 bedrooms

Windsor, Berkshire

Wraysbury Dream

Wraysbury Dream

  • 10 guests

  • 4 bedrooms

Wraysbury, England

A Day at the Regatta

A Day at the Regatta

  • 14 guests

  • 4 bedrooms

Dorney, Buckinghamshire

Sunsets & Swan Feathers

Sunsets & Swan Feathers

  • 7 guests

  • 4 bedrooms

Eton, Windsor

Nom de Plume

Nom de Plume

  • 9 guests

  • 5 bedrooms

Dorney, Buckinghamshire

The Windsor Crown

The Windsor Crown

  • 5 guests

  • 3 bedrooms

Old Windsor, England

Gather & See

Gather & See

  • 10 guests

  • 5 bedrooms

Windsor, Berkshire

The Windsor Lookout

The Windsor Lookout

  • 6 guests

  • 3 bedrooms

Windsor, Berkshire

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Check upcoming rates & availability for Sunninghill and Ascot Vacation Rentals for Winter


Frequently asked questions

Browse our remarkable collection of luxury Vacation Rentals for Winter in Sunninghill and Ascot. As only the top 3% of homes go on to become Plum Award winners, you can be certain that your chosen home will be ideal for you. Each home in our range must pass 3 rounds of testing, and comes fully furnished with a well-equipped kitchen, all linen, and essential bathroom toiletries included. Make the most of the chilly season, and wrap up warm in a comfortable Winter Holiday Rental in Sunninghill and Ascot. Reach out to our caring team of experts, who love nothing more than helping you discover the perfect home for your trip.

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