The Southern Highlands is one of the best places in NSW to bring a team together. Within easy reach of Sydney, Canberra and Wollongong, it offers everything from grand country estates and boutique hotels to outdoor retreats, excellent food, wineries and plenty of space to reset.
Whether you are planning a leadership off-site, multi-day conference, team-building event, client gathering or Christmas party, the right venue can set the tone for the whole experience.
At Vino Rosso Tours we can get your team to the venue and help you make the most of the region once you arrive. We create tailored day trips and multi-day experiences, combining corporate transfers, private group transport, food and wine tours, winery visits, country lunches and team-building activities for teams of all sizes.
Whether you need airport transfers, transport between venues or a complete itinerary across several days, we can take care of the logistics so your team can relax and enjoy the experience.
Here are our top 10 recommendations for your business conference and accommodations in the region.
The Gibraltar Bowral
The Gibraltar Bowral is a modern Southern Highlands retreat with updated facilities, flexible meeting spaces and an immaculate 18-hole golf course.
Located just minutes from both Bowral and Berrima, it gives teams easy access to wineries, distilleries, great food experiences and a wide range of local team-building activities.
Great for: Larger corporate groups needing ballrooms, conference facilities and breakout spaces, with accommodation and on-site activities all in one place. It is also a strong option for Christmas parties, end-of-year functions and team celebrations.
Bendooley Estate
Bendooley Estate is one of the Southern Highlands’ most memorable settings for a team retreat, combining purpose-built conference facilities with beautiful grounds, excellent food, wine and accommodation.
Located just outside the historic village of Berrima, the estate offers dedicated spaces for everything from smaller leadership meetings and strategy days through to larger conferences and gala dinners.
Great for: Teams wanting a true all-in-one country retreat, with conference spaces, accommodation, food, wine and activities all within the estate. It is particularly suited to leadership off-sites, client entertaining, longer team retreats and end-of-year celebrations.
Peppers Craigieburn
Peppers Craigieburn is a beautiful heritage retreat in Bowral, combining a purpose-built conference centre with country charm, stunning established gardens, on-site accommodation and a 9-hole golf course.
The property gives teams room to step away from the city and focus, while still being just minutes from Bowral’s restaurants, shops and local experiences. Between sessions, delegates can enjoy the grounds, a relaxed drink or dinner together, and the option to add a winery visit, country lunch or team activity nearby.
Great for: Small-to-medium corporate groups looking for a classic Southern Highlands conference experience with professional facilities, accommodation and a relaxed country feel. It is well suited to planning days, team retreats, conferences and end-of-year functions.
Peppers Manor House
Peppers Manor House is an elegant country estate in Sutton Forest, offering teams a quieter and more immersive Southern Highlands retreat. With heritage character, beautiful grounds, on-site accommodation and dedicated conference facilities, it is a venue where delegates can settle in and properly step away from the office.
Great for: Small-to-medium corporate groups, leadership teams and multi-day retreats looking for a classic country-house experience. It is well suited to strategy sessions, planning days, exclusive-use events and end-of-year celebrations.
The Robertson Hotel
The Robertson Hotel is a grand heritage retreat with the kind of character that makes a team event feel like a proper escape. Located in the village of Robertson, the hotel combines extensive accommodation, elegant event spaces, open fireplaces, gardens and plenty of room for groups to meet, dine and celebrate together.
Great for: Larger overnight groups, conferences and team celebrations wanting accommodation, multiple spaces and a memorable heritage setting. It is a strong option for multi-day retreats, Christmas parties, themed events and groups wanting to add food, wine or outdoor experiences to their program.
Osborn House
Osborn House is a boutique country retreat in Bundanoon that feels more private and considered than a traditional conference hotel. Set among beautiful bushland, it combines stylish accommodation, distinctive event spaces, excellent food and wellness facilities including a pool, spa and sauna.
Great for: Leadership teams, creative off-sites and smaller corporate groups looking for an elevated retreat experience. It suits strategy days, team planning sessions, incentive-style stays and end-of-year celebrations where atmosphere matters just as much as the meeting room.
Berida Hotel
Berida Hotel is a boutique heritage hotel in Bowral, making it a convenient and character-filled base for a smaller team retreat. With comfortable accommodation, a dedicated conference space and the stunning on-site restaurant, Bistro Sociale, it works well for teams who want everything close by without feeling too formal.
Conveniently located next door to Bowral Golf Course, the hotel is also a short drive from Bowral’s town centre, restaurants and Southern Highlands cellar doors.
Great for: Smaller corporate groups, planning days and team getaways looking for a central Bowral location with personality. It is well suited to intimate conferences, client dinners, Christmas parties and teams wanting to mix work with time exploring the region.
Canyonleigh Retreat
Canyonleigh Retreat is a peaceful country property surrounded by bushland and open space, giving teams room to switch off from everyday distractions and reconnect. It offers group accommodation, meeting areas and a range of outdoor experiences, making it easy to combine focused sessions with genuine team-building time.
Great for: Teams looking for an active, outdoors-focused retreat with space to build connection. It suits leadership off-sites, strategy workshops, team-building programs and groups wanting a relaxed, less formal alternative to a traditional conference hotel.
Fitzroy Inn
Fitzroy Inn is a stunning heritage property in Mittagong, centred around a beautifully restored historic building and spacious established grounds. It offers a warm, character-filled setting for team retreats and smaller corporate gatherings, with flexible spaces for meetings, group dining and relaxed conversation.
Great for: Smaller teams, leadership groups and private retreats wanting a distinctive heritage stay. It is well suited to strategy sessions, executive off-sites, client hosting and intimate end-of-year celebrations.
Ardour Milton Park
Ardour Milton Park is an elegant country estate near Bowral, known for its grand heritage character, gorgeous gardens and refined sense of occasion. Its regional setting gives teams the feeling of a proper escape, while still being close to Bowral’s shops, restaurants and local experiences.
With fantastic grounds, spa facilities, luxurious accommodation and dedicated meeting and event spaces, it is an easy place to combine work with genuinely enjoyable downtime. Teams can enjoy the on-site restaurant, a relaxed high tea or private dinner, then make the most of the gardens and peaceful surroundings.
Great for: Executive teams, premium corporate retreats and client events where presentation and atmosphere matter. It is particularly well suited to board meetings, leadership off-sites, incentive stays, gala dinners and end-of-year celebrations.
What the Southern Highlands Has to Offer.
Once the work is done, the Southern Highlands offers plenty of ways for your group to relax, connect and make the most of being away together. From award-winning restaurants and welcoming country pubs to acclaimed wineries, distilleries and local food experiences, there is no shortage of options to build around your stay.
Explore the region’s enchanting countryside, visit the spectacular Fitzroy Falls, or enjoy a team drink in historic Berrima at one of Australia’s oldest pubs. For international visitors, an evening wildlife experience can be a real highlight — with the chance to see kangaroos, wombats and other Australian animals in their natural habitat.
Vino Rosso Tours can help arrange transport and tailored food, wine and sightseeing experiences to complement your Southern Highlands corporate retreat.
