Best Winter Getaways in Stellenbosch in 2026

Join us on the homestead as we share our slower life this winter season.  We’ve put together stays designed around how we like to spend our winters, as a family. Forget summer break, think local winter holiday, cue the cosy with home-cooked meals, conversations around the fire, the mist as we tend to our farmyard animals.

Download our Winter Stays 2026 information pack:

San Gabriel Winter 2026 Packages

San Gabriel Winter Stays

Winter Recess – 3 night weekend getaways for families in Stellenbosch

A winter weekend, the way school holidays are meant to feel. Days are spent indoors and out, puddles, animals, and small explorations.

3 nights designed for families

  • Arrive Friday – Check Out Monday

Includes:

  • Breakfasts (daily).
  • Friday Pizza & Movie Night (kid friendly).
  • Sunday Soup & Bread Night.
  • Kids activity kit.

Valid from 26 Jun 2026 to 20 Jul 2026

Book your stay here

San Gabriel Homestead Stellenbosch

Stay a little longer

Extend your 2 night stay at the Homestead – your 3rd night is our treat! Days soften, routines fall away, and the homestead begins to feel like your own.

Stay 3 nights, pay for 2

Available all week

Includes:

  • An extra night to settle in.

Valid 20 April – 31 August

Book your stay here

1 Night Supper Stays in Stellenbosch

A Midweek Retreat

An evening of shared food, conversation, and candlelight… simple, generous, and memorable.

Arrive Wednesday – Checkout Thursday

Includes:

  • Kitchen Dinner (long table)
  • Breakfast.

Valid from 20 Apr 2026 to 31 Aug 2026

Book your stay here

 

Why We Are Staying in the Stellenbosch Winelands This Winter

Every year during the quieter months, we take a family holiday—usually to the bushveld or somewhere warm. But this winter, with our second baby boy arriving in June, we’re staying home in the Stellenbosch Winelands. And honestly, nothing beats curling up with a newborn during the cozy winter months.

Many of our international guests ask, What is winter really like in the Cape Winelands? And because it’s our slower season, I tend to switch off and forget to notice much. But scrolling through my camera roll, I was reminded that the real rainy season only peaks in July and August. The rest of the time, we’re outside in a light jersey and jeans—not even close to a European winter!

 


 

 

What’s Winter Like in the Stellenbosch Winelands?

 

Unlike the deep freezes of the Northern Hemisphere, Stellenbosch winters are mild and charming. Expect daytime temperatures between 8°C and 18°C (46°F – 64°F), with crisp mornings and bursts of clear skies between soft, rainy days. It’s the kind of winter that invites slower mornings, long walks, and evenings spent by the fire.

If you’re looking for a quieter, cozier, more authentic South African experience—winter in the Winelands is a hidden gem.

 


 

 

What I’m Looking Forward to This Winter

 

With a newborn joining us this June, I’m leaning into the rhythm of home. Still, there’s so much I’m looking forward to this season:

 

1. Family-Friendly Hikes

 

The softer winter sun makes it a joy to be outside. We’re lucky to have two of our favourite walking spots right nearby:

 

  • Jonkershoek Nature Reserve – A dramatic valley with family-friendly trails, waterfalls, and fresh mountain air.
  • Helderberg Farm – Just across the road from San Gabriel and walkable from our property, this is our go-to for spontaneous outings with our toddler, picnics, and wide open spaces.

 

This year, we’re also planning to discover a few new trails—will report back on our favourites as we find them.

 

And on the quieter days, we love taking warm flasks of hot chocolate and heading to the beach. The air is crisp, the crowds are gone, and we get the sand all to ourselves—collecting shells, jumping over waves, and ending up in spontaneous sand fights. It’s simple, messy, and completely magical.

 

 

 

2. Cabernet Sauvignon & Home-Cooked Meals by the Fireplace

 

Stellenbosch is the Cabernet Sauvignon capital of South Africa, and winter is when the bold reds truly shine. Pair a glass of local Cab Sav with a homemade stew or slow-cooked lamb, and you’ll understand why this is my favourite food-and-wine season. Plus, with the fireplace going and a sleeping baby nearby, it’s the kind of scene you dream about.

 

3. Wine Town Stellenbosch (26 July – 3 August)

 

One of the highlights of the winter season! Last year I attended the Wine School event at Wine Town with a friend and was completely drawn in. We learned how to taste properly, explored different wine styles, and got to chat with some of the region’s top winemakers. This event brings Stellenbosch’s wine culture to life—with masterclasses, tastings, and special events hosted throughout the historic town.

 

4. Museums & Art Galleries

 

Winter is also a wonderful time to explore the cultural side of Stellenbosch. Some of our favourites include:

 

  • Soetmelksvlei – A living museum that’s both inspiring for adults and fun for kids, with vintage interiors, indoor displays, and outdoor play areas.
  • Rupert Museum – A quiet gem with beautiful exhibitions and winter workshops for adults and children alike.
  • Dylan Lewis Sculpture Garden – Still absolutely breathtaking in winter. The misty garden paths winding between powerful sculptures make it feel like stepping into a dream.

 

 

5. A Winter Baby & A New Season

 

Having a baby is unpredictable—I still remember Basson’s first holiday at six weeks old in the icy Calvinia. This time, I’m embracing a slower season close to home. Winter gives us permission to pause, to nest, to do less. I’ll be sharing moments from this new chapter as the season unfolds.

 


 

 

Our Winter Stay Package

To celebrate this slower, cozier season, we’re offering a special winter package at San Gabriel:

 

  • A bottle of Cabernet Sauvignon from our neighbours at Happy Vale,
  • A hearty, homecooked farm meal, ready to heat in the oven,
  • A freshly baked loaf of bread from our local bakery,
  • And a generous slab of farm-churned butter, made by Renier himself.

 

It’s our way of inviting you into our way of winter living—simple pleasures, warming food, and a real taste of the Winelands.

👉 BOOK THIS PACKAGE

 


 

If you’re dreaming of crisp air, red wine, crackling fires, and quiet moments—winter in Stellenbosch is waiting. It may not be our biggest season, but it just might be our best-kept secret.

We hope to welcome you soon. And if you’re already booked in—we can’t wait to share this season with you.