• Rooms
    Double Room

    Double Room

    Max 2 guests
    1 Double bed

    Enter dates to check availability

    Twin Room

    Twin Room

    Max 2 guests
    2 Single beds

    Enter dates to check availability

    Need help? Speak to our Reservations Team on +44 203 397 0085 or email us
    Opening Hours 09.00 - 18.00 Monday - Friday (UK time)
  • Overview

    Why so chic?

    Why travel experts chose this hotel
    • Easy reach of Ascot and Windsor

    • Fabulous food

    • Cosy 18th-century inn

    Chic Treats

    Only when you book with Chic

    Room upgrade (subject to availability)

    Early check-in/ late check-out (subject to availability)


    Within easy reach of Ascot and Royal Windsor racecourses, the aptly named The Winning Post is one of the Upham Group's gastro pubs in Winkfield, Berkshire, with 12 charming boutique hotel rooms. This 18th-century inn has plenty of cosy nooks, original stone floors and a huge open fire.

    Within easy reach of London Heathrow airport, The Winning Post is a great choice if you have an early flight or late arrival.

    Ascot and Windsor are both just down the road and are home to some fantastic horse racing and the Royal Windsor Horse Show.

    The PGA Championships take place at the world famous Wentworth Club in nearby Surrey and the Henley Royal Regatta is a favourite amongst return guests.

    Kids (and adults!) will love a trip to Legoland, and if you love theme parks then head to Thorpe Park in the neighbouring county, Surrey.


    Their chef is passionate about local culture and menus and has travelled the world creating fabulous dishes. His focus is and always has been on authentic flavours using local, seasonal produce.

    Expect meticulous presentation and constantly changing menus using the best short season produce such as asparagus, grouse and native lobsters.

    The real ales on the extensive drinks menu are brewed by the Upham Brewery in Hampshire by a small, dedicated team using traditional methods.

  • Facilities
    • bar

    • car parking

    • pets allowed

    • restaurant

  • Location

    Winkfield Street, Winkfield, Windsor SL4 4SW, United Kingdom

    How to get there?

    Leave the M4 at Junction 6 then at the roundabout take the 1st exit onto the A355. At next roundabout take the 3rd exit onto Imperial Road – B3175. At traffic signals turn right onto Saint Leonards Road – B3022. At the 2nd roundabout take the 2nd exit onto North Street – B3022 (signposted Winkfield). Continue forward until you go through the village of Winkfield and come to a sharp left hand bend. Turn right at this sharp left hand bend into Winkfield Street. The Winning Post is 200 yards on the right.

    Nearby rail stations:

    Ascot (4 miles), Bracknell (4 miles), Windsor (6 miles) and Maidenhead (7 miles)

    Nearest airport

    The nearest airport is London Heathrow Airport, a twenty-five-minute drive (Approximately 14.9 miles distance). 

  • Conditions
    Payments policy

    100% deposit is required at the time of booking.

    Cancellation policy

    If a cancellation is made within 2 days of the arrival date, 100% of the total price will be charged.

    Check-in/check-out policy

    Check-in time: 13:00

    Check-out time: 11:00

    Early check-in: no

    Late check-out: no



Each hotel specially selected for its unique charm


Special benefits only guests booking through Chic Retreats obtain.


If you find your stay cheaper elsewhere we will give you £50 towards your next stay with us.


Please ask for details about our airport transfer service

Need help? Speak to our Reservations Team on +44 203 397 0085 or email us
Opening Hours 09.00 - 18.00 Monday - Friday (UK time)