20 Cummings Street boasts a warm and inviting atmosphere, originally renovated in 1993 as the Visser family's residence. In 2001, Mattie, co-owner and hostess, recognized the growing need for accommodation in Wellington and quickly transformed Cummings into a popular and highly sought-after destination within just three years. With Mattie's dedication and exceptional service, Cummings Guesthouse became a renowned name in Wellington's hospitality scene. In 2022, Mattie welcomed her daughter, Wilma, as the new manager, marking an exciting generational shift.

Cummings Guesthouse, nestled in the heart of the picturesque Winelands, is the ideal retreat for business travellers, solo adventurers, and families alike. Our well-appointed rooms feature modern amenities such as air conditioning and complimentary high-speed fibre Wi-Fi. When the weather warms up, our inviting pool is the perfect place to take a refreshing dip (pool towels provided). We provide quality linens and towels as part of your room rate, ensuring your comfort throughout your stay. Coffee and tea facilities are available in all rooms, along with bar fridges, kettles, and hairdryers. Each room boasts an en-suite bathroom with a shower, toilet, and basin. For added convenience, our self-catering rooms are equipped with kitchenettes, basic cooking utensils, and microwave ovens. All rooms include Smart TVs, allowing you to stream your favourite content during your stay. Our guesthouse is supported by a solar power system, helping to minimise the impact of loadshedding and ensuring a more comfortable and uninterrupted experience for our guests. Rest easy knowing that secure on-site parking is included at no extra charge, with one designated parking space per room. For those who love to braai, we offer dedicated braai facilities and provide essentials like tongs and braai grids. Our hearty breakfast is served daily from 07:00 to 09:00, setting you up for an exciting day of exploration. At Cummings Guesthouse, we aim to make your stay feel like a home away from home. Your requests and questions are always welcome, and we're here to assist you in any way possible. We can’t wait to welcome you soon.

Nestled in a quiet residential neighbourhood in Wellington, the guesthouse is just a short drive or even a pleasant stroll away from the town centre. Its proximity to the church, high school, local coffee shops, and the town's museum makes it an ideal base for exploring the Winelands. The surrounding area is teeming with wineries, restaurants, and some of the world's most stunning hiking and mountain biking trails, providing a diverse range of activities for visitors.