Book Luxury Vacation Rentals for May in Sunninghill and Ascot

We selected the 5948 homes worth renting in this location

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Home spotlights in Sunninghill and Ascot

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.

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 Whistler

The Whistler

  • 7 guests

  • 4 bedrooms

Old Windsor, Berkshire

This elegant 19th-century home is nestled within the grounds of the former Old Windsor Tapestries factories. It's surrounded by well-maintained communal gardens, but you'll have your own private terrace, too.

Secret Garden Games

Secret Garden Games

  • 8 guests

  • 5 bedrooms

Burnham, Slough

Despite being tucked away on the outskirts of Burnham village, it’s worth noting that this historic home is situated by the side of an – albeit fairly quiet – road. Although both cosy and capacious – featuring five bedrooms as well as separate breakfast, dining and sitting rooms – we’ll bet it’s this home’s four-poster bedroom and en-suite marble bathroom you’ll be fighting over.


We selected the top 3% holiday homes in Sunninghill and Ascot Vacation Rentals for May

Explore the 5948 most perfect homes in our collection

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Most popular homes in Sunninghill and Ascot

Forgotten Fields

Forgotten Fields

  • 2 guests

  • 1 bedrooms

Tetsworth, Thame

The Song Bird

The Song Bird

  • 2 guests

  • 1 bedrooms

Cranleigh, Surrey

A Day at the Regatta

A Day at the Regatta

  • 14 guests

  • 4 bedrooms

Dorney, Buckinghamshire

The Belgian Ambassador

The Belgian Ambassador

  • 8 guests

  • 4 bedrooms

Bray Civil Parish, Berkshire

Stately in Surrey

Stately in Surrey

  • 6 guests

  • 3 bedrooms

Chobham, Surrey

Ebony & Ivory

Ebony & Ivory

  • 7 guests

  • 4 bedrooms

Highway, Maidenhead

Stud Cottage

Stud Cottage

  • 2 guests

  • 1 bedrooms

Billingshurst, West Sussex

Surrey Hills Manor

Surrey Hills Manor

  • 16 guests

  • 8 bedrooms

Tadworth, Surrey

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Frequently asked questions

Discover our exclusive collection of the finest Vacation Rentals for May that Sunninghill and Ascot has to offer, and mark the month with an unforgettable trip. At Plum Guide, we carefully select only the very best homes around, so you know that every rental is one to be proud of. Each home in our range comes fully furnished, with a well-equipped kitchen, all linen, and essential toiletries included. Our meticulous testing process ensures that no stone is left unturned, with everything from shower pressure and Wifi speed to a home's design aesthetic being thoroughly tested. Book a luxury Holiday Rental for May in Sunninghill and Ascot today, and see what all the fuss is about. If you need any guidance, call on our experts, ready night and day to help you find your ideal home.

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