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There's something magical about the Southern Highlands. Made up of a series of leafy villages—including Bowral, Bundanoon, Robertson, Sutton Forest, and historic Berrima—well-heeled Sydneysiders have been visiting the area for well over a century for a city escape and a welcome dose of crisp country air.
The Southern Highlands is Gundungurra Country, some 700m above sea level on the Great Dividing Range with spectacular mountain outlooks, waterfalls, and wiery bushland to explore. Unlike the Blue Mountains, however, rows of planted oak and elm trees and sprawling country manor houses give the Southern Highlands its much-loved romantic English countryside aesthetic.
It's also one of NSW's noted wine regions, with around 60 vineyards growing cool climate Pinot Noir and other tasty drops.
Southern Highlands Airbnbs
Sutton Forest Fantoosh
This fairy-tale-like cottage is perfect for a couple keen on a quiet escape to the Southern Highlands with a few little luxuries. Like heated floors, a roomy bathtub for soaking, and an outdoor fire pit.
Fantoosh is also a friendly distance from the region's best cellar doors (Centennial Vineyards and Bendooley Estate), pubs (The Sutton Forest Inn), and wedding venues (Somerley House, Montrose House).
Bowral The Potting Shed
This adorable converted garden shed is perfect for a couple looking for a cosy weekend getaway.
Overlooking a vegetable garden, The Potting Shed features a plush king-size bed, a kitchenette with room for breakfast, a large tub with a view of the garden, a sunny nook to work if you need, and a private patio. It might be small, but it's all you'll need to escape the hustle and bustle.
Sutton Forest The Boscobel Estate Guesthouse
This ultra-charming guesthouse is a covered stable. On the grounds of the 120-acre heritage-listed 1860s Boscobel homestead, you'll be surrounded by sweeping paddocks, friendly horses, spring-fed dams, and historic estate buildings.
Inside, the guesthouse sleeps up to four and you'll find a full list of modern amenities (Nespresso machine with pods provided, dishwasher, heaters, and air conditioning). There's also an outdoor hot tub with a view across the property.
Exeter Classic Chic Traditional Barn
Channel all your Yellowstone-inspired dreams at this special two-bedroom farm stay in Exeter. It might look like a traditional barn, but you can expect a long list of luxe amenities like underfloor heating, a fully equipped kitchen, and a huge tub with a skylight above.
As for the farm, your friendly neighbours are ducks, chickens, alpacas, and black-faced Suffolk sheep.
Bowral Dunrana Cottage
Perfect for a romantic escape, this cosy studio has all the essentials for a perfect Southern Highlands weekend. A private courtyard, open plan bedroom, kitchen, and bathroom, all super close to the best of Bowral and beyond.
You'll be a short stroll away from the centre of town, as well as other local attractions like Cherry Tree Walk and (for warmer months) the local swimming pool.
Kangaroo Valley Barranca
Set deep within the valley on the rolling green hills of Australia's oldest Shire horse stud, Barranca features four luxury villas. Each villa peers out onto a spectacular scene of uninterrupted rainforest and a dramatic sandstone escarpment that glows burnt orange just before the sun sets.
Villas are roomy (for four–eight guests) and come kitted out with a fire pit, fully equipped kitchens and bathrooms, smart TV, fireplace, and more. Aside from all the natural beauty and luxe amenities at your fingertips, the property is home to horses, pigs, and a few friendly buffalo—and you're welcome to feed the animals each morning.
Southern Highlands Airbnbs For Groups
Exeter Ellery Farm
With space for up to 10, this architecturally designed retreat looks like a Grand Designs masterpiece—and it is perfect for a luxe group getaway.
Set on 25 acres of rolling green hills in Exeter, you'll have everything at your fingertips—a spacious open-plan kitchen with designer appliances and a huge dining table for group dinners, a kids retreat, Foxtel, Netflix, and Apple TV, a huge deck and bbq area with a fire pit, and a master suite complete with a deep stone bathtub for pure relaxation.
Bowral Heritage Coach House At The Rift Estate
Set on the rolling green heritage-listed gardens of grand old The Rift Estate in Bowral, The Coach House has space for 13 across six bedrooms.
The converted home used to accommodate coachmen and horses, who would be tending to the late-nineteenth-century Italianate mansion. Expect luxury country living at every turn, complete with a lawn for croquet and badminton and bushwalking trails and scenic paths to explore nearby.
Joadja The Seidler House
This one is for the design lovers out there. The Seidler House is considered to be one of the late Harry Seidler's residential masterpieces, built into a natural sandstone cliff escarpment in Joadja in the Southern Highlands.
Beneath the rolling curve of the roof, floor-to-ceiling glass windows peer out onto the wide gulley below, while Alta quartzite floors, Verde marina granite, and Norwegian stone make for an ultra-luxurious interior. Then, there are the viewing decks, gardens, sculptures, and a central swimming pool. The house sleeps eight with four bedrooms—perfect for a luxe group getaway.
Southern Highlands Tiny Homes
Moss Vale Hideout
This pint-sized cabin is perched right by a dam, and we can't think of a better spot to escape the city hustle than with a cup of tea and a good read while sitting out on the deck. While it is on an idyllic farm, this hideout is anything but provincial. It's decked out with designer finishes, luxe bed linens,
Egyptian cotton towels, and a plush queen-sized bed. You can also opt to go on a horse ride around the farm if you want to soak up that fresh country air. At night, get the fire pit roaring and gaze up at the stars.
Moss Vale Hideout 2.0
The team behind Hideout knew they'd created something so good, they went and set up a second tiny home. This tiny home is off-grid and completely solar-powered, with a large deck and views out across a working horse farm.
Cosy up by the outdoor firepit, schedule a horse ride, or get out and explore the best of the Southern Highlands. You are a 10 - 15 minute drive from popular wedding venues, Bendooley Estate, Centennial Vineyards, and Milton Park.
Southern Highlands Hotels
Bundanoon Osborn House
Osborn House is a stunning, stately manor, complete with 15 unique suites and seven self-contained cabins, each looking out onto the beautiful garden and forest beyond. Design lovers will swoon over the property's magnificent details. The interiors are the work of London-based designer Linda Boronkay (Soho House) alongside Sydney-based Mac Design Studio, led by interior architect Alan McMahon.
As well as looking the part, at Osborn House, you can also indulge in the 25m lap pool and an ultra-luxe spa with four treatment rooms, a sauna, steam room, cool plunge, and gym. The on-site restaurant is led by executive chef team Segundo Farrell and Luz Gimenez, with a focus on cooking over fire.
Bowral Milton Park Country House Hotel And Spa
Milton Park Country House is a converted manor house inspired by the country hotels of Europe. Basically, if Downton Abbey is the mood you're in, this is the spot to live and breathe it. Milton Park is a popular spot for weddings thanks to its romantic gardens.
Prep your camera for the ivy-covered pool house, wisteria archways, and bluebell fields, book a garden suite to wake up to views of the courtyard and rolling green paddocks beyond, and schedule a little self-care time at the luxurious wellness spa.
Sutton Forest Peppers Manor House
Complete with two tennis courts, croquet, boules, and a luxurious pool room, Peppers Manor House in Sutton Forest is another European-inspired retreat with old-world English charm. There are 43 suites, each brimming with country charm and views across rolling green gardens and deciduous trees.
There's an on-site bar and restaurant (Katers) if you don't want to travel far, a roaring fire and board games in the lounge, and an outdoor swimming pool for warmer weather.
Bowral Park Proxi Gibraltar
A few minutes outside of Bowral, the recently refurbished Park Proxi Gibraltar hotel overlooks a golf green and the wooded hills of Mount Gibraltar. Rooms are extra spacious, making it easy to spread out and unwind after a long day of exploring the Southern Highlands.
The 18-hole resort-style golf course will keep keen golfers happy, while a heated indoor swimming pool, gym, and multiple on-site dining options are perfect if you'd prefer to cosy up at the hotel.
Image credit: Osborn House | Instagram
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