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Luxury Accommodation in the Southern Highlands

Linger a little longer in this cluster of country towns by booking a night at one of these luxury Southern Highlands accommodations.

Kangaroo Valley

The Southern Highlands has long been favoured as a weekend retreat from city life. And with its rugged landscape, cascading waterfalls, cool-climate vineyards, beautiful restaurants 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.

Read on for our edit of luxury Southern Highlands accommodation.


The CASA is a luxury home nestled in the picturesque Kangaroo Valley that beautifully blends history and modern design. Originally an art gallery showcasing renowned Australian artists, it has been reimagined into a peaceful country getaway with a stunning eco-style farmhouse and sprawling estate. 

Grand cedar beams, white-washed mudbrick walls, and landscaped gardens enhance the home's natural beauty. Warm and earthy interiors blend seamlessly with natural materials, creating a relaxed and inviting atmosphere. The home sleeps up to 20 guests making it ideal for large families or group gatherings, and with a pool and cabana, tennis court and firepit ideal for toasting marshmallows it's the perfect house to stop and stay a while. 

Kangaroo Valley 

Moss Manor

Nestled in the picturesque Southern Highlands, Moss Manor is the epitome of historic charm and contemporary luxury. This boutique hotel, set within a beautifully restored Georgian manor provides a unique escape into a world where classic elegance meets modern design.

From the moment you step through the doors, you are greeted with an afternoon tea that features freshly baked cake and a choice of tea or coffee—a perfect welcome that sets the stage for a stay marked by indulgence and comfort. The interior of Moss Manor invites relaxation, from the cosy warmth of its inviting fireplaces to the plush lounge areas, where the air is infused with calming incense creating a sanctuary.

The guest rooms at Moss Manor are a lavish affair, each plush and spacious, offering a sumptuous retreat. The Sophia Suite, in particular, is ideal for those looking to indulge a little during their stay. Every aspect of Moss Manor speaks of a thoughtful blend of comfort and style, making it a difficult place to leave and a delightful place to return to, time and time again.

1A Throsby Street, Moss Vale

The Rift Estate

The Rift Estate

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

Osborn House

Osborn House

New South Wales’ picturesque Southern Highlands welcomed Osborn House in 2022, an impeccably designed five-star boutique hotel surrounded by rolling hills and manicured grounds. The 130-year-old property has been lavishly restored, but its century-old gardens and well-appointed lodgings – complete with vintage furnishing and bespoke design elements – hint at its past.

Along with 22 character-filled yet contemporary rooms, the estate has a day spa with a slew of luxe treatments and services as well as top-tier dining options in Gorge's and Dinah’s.

96 Osborn Avenue, Bundanoon

Milton Park Country House Hotel & Spa

Milton Park Country House Hotel and Spa

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

Peppers Manor House

Peppers Manor House

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 – preserve its historic charm. 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

The Cottage

THE COTTAGE Kangaroo Valley

Owned and curated by artist and stylist Lisa Madigan, The Cottage flaunts interiors just as breathtaking as its idyllic surrounds. A carpet of lush greenery awaits outdoors, whilst indoors, Lisa's stylish sanctuary beckons in all its white-washed serenity

An uplifting space of calm and rejuvenation where exposed brickwork, raw woods, and scatterings of greenery effortlessly combine to create a sense of rustic, laid-back luxury. With just one bedroom, this charming retreat is built for two, so get ready to bask in tranquillity and soak up the romance. Explore the majestic landscapes of Kangaroo Valley then settle down with a glass of wine and let the sofa do the talking. 

118 Moss Vale Road, Kangaroo Valley

Bendooley Estate Cottage

Bendooley Estate Cottage

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

Park Proxi 

This modern hotel is the perfect spot to base yourself for a weekend of exploring the best of Bowral. With an indoor pool, 18-hole golf course, restaurant and bar, all the comforts are accounted for. When it comes time to venture out, you're just a two-minute drive from Centennial Vineyards, a three-minute drive from the shops and a 12-minute walk from a scenic stroll through Gibbergunyah Reserve. 

Corner Boronia Street and Centennial Road, Bowral

Siedler House

Siedler House

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).

Lake David

Lake David

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

Peppers Craigieburn Bowral

Peppers Craigieburn Bowral

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 look out over the garden and you can mingle in the guest lounges in front of open fires. #bliss

Centennial Road, Bowral

Found your luxury accommodation in the Southern Highlands and need to work on an itinerary? Check out our edit of the best restaurants in the Southern Highlands. Once you're done there, take a peek at our guide to Bowral.

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