The Southern Highlands has been long-favoured as a weekend retreat from city life. And with its rugged landscape, cascading waterfalls, cool-climate vineyards and grand estate homes, it’s little wonder that Sydneysiders escape to the Southern Highlands whenever they can. Just 90 minutes from the city, the cluster of charming country towns is just waiting to be explored – so rather than settling for a day trip, linger a little longer and stay overnight.
Here is our edit of the most beautiful Southern Highlands accommodation.
When it comes to luxury, countryside accommodation, you can't go past Exeter's Ellery Farm. This architecturally designed home boasts four bedrooms, modern furnishings, open plan living, and a state-of-the-art kitchen, making it the perfect place to book for a group getaway or family retreat. Kitted out everything you need for an unforgettable stay, we guarantee you'll find any excuse to extend your weekend trip into a week-long sojourn.
From $957.14 per night
340 Ellsmore Road, Exeter
Dotted with manors and English country gardens, Bowral is as picturesque as it gets, and The Rift Estate is one of its shining stars. Built in 1890, the mansion sits on 2.7 hectares of gardens, and its stables have been converted into a six-bedroom home, The Coach House. The property features claw foot baths, fireplaces and underfloor heating, and can accommodate up to 13 people.
8 Carlisle Street, Bowral
The Southern Highlands has long been a retreat for Sydney’s elite. To join them, book a room at the five-star Milton Park Country House Hotel and Spa. If we had to use one word to describe it, it’d be ‘grand.’ Set on 120 hectares of hilltop woodlands, it has tree-lined walkways, four-poster beds, marble bathrooms, a Wellness Spa, and more antiques than you can count. For a luxe Southern Highlands accommodation, this is it.
200 Horderns Road, Bowral
The Highlands is steeped in history, and Peppers Manor house is at its heart. The 140-year-old hotel has had a multi-million dollar makeover, but its formal gardens and Great Hall – complete with soaring ceilings, couches and a roaring log fire – hint at its past. It has all the mod cons for a comfortable stay, plus an 18-hole championship golf course, and the chef-hatted Katers Restaurant.
Kater Road, Sutton Forest
Bookworms – Bendooley has the makings for a memorable weekend escape. Bendooley Estate is home to a vineyard, cellar door, and a restaurant that’s lined with new, second-hand and rare books. It’s beyond charming, and if you don’t want to leave, you really don’t have to. Across the manicured grounds, is some of the most beautiful Southern Highland accommodation; a studio, two- and three-bedroom cottages, decorated with plush, French provincial furnishings.
Bendooley Estate, 320 Old Hume Highway, Berrima
Nestled in the rolling hills of Mt Gibraltar, this elegant hotel is a popular spot for weddings. Along with 76 luxe yet understated rooms, the property has an 18-hole golf course, an indoor heated pool, a gym and a day spa with a slew of treatment rooms plus a ‘Serenity Room’. It also backs onto the Gibbergunyah Reserve, a bushwalking haven.
Corner Boronia Street and Centennial Road, Bowral
This striking sandstone, concrete and glass home is a Harry Siedler masterpiece. The late architect was known for his jaw-dropping designs, and this house lives up to his reputation. Located between Mittagong and Bowral, Siedler House is built into the natural rock formation, and its floor-to-ceiling glass walls offer panoramic views of the bush and Wingecarribee River. It has four bedrooms, BBQ facilities, a balcony and swimming pool.
Richards Lane, between Mittagong and Bowral (exact address shared upon booking).
For the ultimate Southern Highland accommodation that caters well for groups, then this is it. Gather your nearest and dearest and rent Lake David, a gorgeous, resort-style home in Kangaroo Valley. Perched on the edge of Lake Yarrunga, the architectural masterpiece is kitted out with a chef’s kitchen, games room, tennis court, indoor and outdoor entertaining areas, and a private swimming pool with a Jacuzzi. It sleeps up to 18 people.
Jacks Corner Road, Kangaroo Valley
This heritage resort is set on 36 hectares of beautifully manicured estate gardens that comes complete with a 9-hole golf course. Exuding the allure of times passed, Craigieburn retains the elegance of the original building but with modern décor. Guestrooms lookout over the garden and you can mingle in the guest lounges in front of open fires. #bliss
Centennial Road, Bowral
Once a bank dating back to the 1880s, this building was turned into a luxurious boutique Southern Highlands accommodation a few years ago. There are five rooms featuring rich fabrics, high ceilings, hand-carved wood panelling, and polished floorboards, and two self-contained cottages out back. Downstairs, there’s a lounge and library, and the star attraction: a restaurant and wine cellar in the former bank vault.
83 Main Street, Mittagong