Cape Town South Africa - Simon's Town

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Cape Town Accommodation, Tours & Travel


Simons Town Accommodation

Welcome to the Winston guest house, a four star establishment which offers luxury accommodation in the heart of historic Simons Town. Guests can relax indoors or outside on the pool deck; where there is always an opportunity to glance at the stunning views, spanning from Simons Town across False Bay, towards the floral Cape Point. Whale watching is one of the many highlights when staying at The Winston, guests can watch these majestic whales in the privacy of their own rooms, or can take a brief stroll down to the beach; which is a mere 50 meters from the False Bay coast line. Alternatively guests can take a short walk to the Boulders Beach and reserve, where they can share the company of the famous and protected colony, of Jackass Penguins.

Each morning this fine bed and breakfast establishment serves a full English or Continental breakfast accompanied by sea views and a friendly atmosphere. To ensure guests are always entertained, Simons Town offers many restaurants, art galleries boutique shops and a waterfront harbor. Stay here for the comfortable accommodation, seaside ambience and friendly hospitality.

There are five beautifully appointed spacious suites, each tastefully decorated in a fresh Cape Cod look; boasting lavish en suite bathrooms, with deep set baths and marble showers with extra large shower heads. The rooms come standard with comfortable facilities such as Satellite TV with DSTV; and a superb tea and coffee making station. The room’s large glass sliding doors open up onto the tiled patio and entertainment area, where guests can take a refreshing dip in the pool, or enjoy sundowners with the backdrop of a panoramic view of False Bay looking across from Simons Town to Fish Hoek, Kalk Bay Muizenberg to The Strand, Gordon’s bay and Cape Hangklip.

History of The Winston Guesthouse in Simonstown

My father who was commonly known as “Major” retired from the SADF in 1966. After which he then relocated with my mother Nancy to Port St Johns, previously known as the Transkei. Ports St Johns was home to my mothers family for many years, starting with my Great Grandfather who was one of the first settlers in the village. The family owned two hotels in the village named The Winston Hotel and The Needles Hotel. My parents contributed in the running of both hotels and soon become a well known colourful couple in Port St Johns.

This family tradition of running hotels continued when I opened my first lodge aptly named Needles and later the Winston in Simons Town. The establishment of both properties has been foreseen by the 14 years of industry experience of Theo and my daughter Kim’s wise advice.


  • Tea trays in all rooms
  • Satellite TV in all rooms
  • Internet
  • Laundry service
  • Honour bar
  • Hair Dryers in all suites
  • Fax and phone available
  • E-Mail and internet available
  • Outside pool deck
  • Full English breakfasts and continental breakfast on request
  • Tailor made full and half day tours with a qualified guide - upon request
  • Airport transfers upon request
  • Restaurant bookings

    Where Are We?

    The Winston is located 5 minutes outside of Simonstown.
    Turn Right into Rocklands Road and then your first right into Erica Road.
    The Winston is the first house on your right
    The journey from the Airport takes approximately 45 minutes



    1st May 2008 TO 31st August 2008:
    R495.00 Per Person Per Day : Bed and Breakfast.
    Single Supplement:R650.00

    1st September TO 30th April 2009
    R600.00 Per Person Per Day : Bed and Breakfast.
    Single Supplement: R750.00


    Contact Details

    Phone:    +27 (0)21 786 1700
    Fax:        +27 (0) 86 554 8847
    Mobile:    +27 (0) 83 460 1435


    Physical Address
    15 Erica Road
    Murdock Valley South
    Simons Town

    Postal Address
    15 Erica Road
    Murdock Valley South
    Simons Town


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  • The Winston

    The Winston



    Unwind at the Pool

    Unwind at the Pool

    Bed and Breakfast Room

    Bed and Breakfast Room

    Patio View

    Patio View





    Relax and Unwind

    Relax and Unwind