23 Editor-Approved Southern Highlands Stays For An Epic Weekender

Just 90 minutes from Sydney, ARUNA Estate feels worlds away from the daily grind. Set among native bushland in the Southern Highlands, this thoughtfully designed retreat combines luxury villa accommodation with working farmland, regenerative agriculture, and sweeping forest views. Floor-to-ceiling glass walls frame the surrounding landscape, while polished oak floors and warm, minimalist interiors create a sanctuary that's stylish and serene.

Each villa overlooks a valley lined with Australian Blackwoods and Lilly Pillies, with views stretching towards Penrose State Forest. Days here can be spent hiking or mountain biking through nearby trails, stretching out on the property's yoga deck beneath a towering eucalyptus tree, or simply soaking up the scenery from your private deck. To make things even sweeter, every stay comes with a generous hamper packed with local wine, cheese, sourdough, olives, and breakfast essentials.

There are plenty of cabins in the Southern Highlands, but few feel quite as special as this architect-designed retreat hidden among the paddocks near Berrima. Built by hand over three years and completely off-grid, the secluded stay is designed for immersing yourself in nature. In the mornings, you can watch kangaroos roam across the property—whilst evenings are best spent gathered around the fire with nothing but stars overhead. It’s only 90 minutes from Sydney, but it feels a world away.

Inside, warm blackbutt timber, a wood-burning Bakeheart fireplace, and thoughtfully curated interiors create a rustic and refined atmosphere. The mezzanine king bedroom sits beneath skylights, allowing guests to stargaze from bed, while a hand-forged ladder leads to an observatory loft for even better views of the night sky. Outside, a wraparound deck, fire pit, and outdoor dining area overlook the surrounding farmland, where wombats, cattle, and native wildlife are all part of daily life.

Fancy a spot of wine-tasting with the other half and doggo in tow? This adorable pet-friendly Airbnb in the heart of Sutton Forest is a top choice from which to explore the Southern Highlands' vineyards. You’re a 20-minute drive from the dog-friendly Centennial Vineyards here, and close to Bowral with its charming shops and eateries.

Your accommodation has heated floors and an indoor fire, plus a fire pit to snuggle around outside come nightfall. The champions that own this place supply firewood for your stay, and provide super fast internet for that post-dinner movie. 

This adorable converted garden shed is a top accommodation spot for a couple looking for a cosy weekend getaway in the Southern Highlands, and it gets bonus points for being toddling distance into Bowral.

Overlooking a gorgeous veggie garden designed by Australian garden designer Paul Bangay, 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.

Say hello to Hamptons vibes with a stay at Colyersdale Cottage, a two-bedroom stay that sits pretty on a 350-acre cattle farm just ten minutes out of Moss Vale. It’s a five star-rated Southern Highlands accommodation option that’s perfect for two couples, as it has two King-size bedrooms, each with a walk-in robe and a handy ensuite.

Pour yourself a steaming cuppa and stroll on out to the epic outdoor dining terrace. There’s a swing seat here to perch on as you sip, plus a barbecue and an outdoor fireplace which keeps you pretty cosy in the cooler months too. 

Got family to accommodate? It’s no problem here as the King beds can be split into two singles and a foldaway bed with bedding can also be supplied on request.

Perfect for a romantic escape, this cosy weatherboard studio has all the essentials for a perfect Southern Highlands weekend. It offers open plan living, with a tidy bedroom, kitchen, and bathroom, all just 700 metres from the centre of Bowral and close to the local vineyards and golf course.

Your home away from home is striking inside, thanks to its monochrome features and it’s got a fully-fenced backyard where you can sit at a stone table and enjoy a cuppa. 

It’s the location that really sells it though, as you are so close to town, and can wander to the beautiful Cherry Tree Walk or visit the local swimming pool in no time at all.

Set deep within the valley on the rolling green hills of Australia's oldest Shire horse stud, Barranca features four luxury Airbnbs. 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.

Say hello to the Suffolk sheep and resident alpacas Albert and Archie. They’re going to be your besties for a while if you stay at Woodland Studio. This Southern Highlands Airbnb is set on a small farm just 20 minutes from Bowral and 3km from the charming Exeter village, and we love the fact that it’s pet-friendly, so you can bring your own four-legged friend too. Woo!

Your pad is big enough to house two couples, with a king bed in the main studio and another king in the second bedroom (which can be converted to two singles if you prefer). Kick back and relax in the separate snug room, or dig out the bocce set and have a game in the private, fenced backyard. The folks that own this place provide breakfast items for your first day’s stay and say you’re welcome to explore the farm and help yourself to any fruit in season if you see it.

Experience a bit of animal magic at this Southern Highlands stay. It's got three alpacas, a horse, a miniature donkey and two huskies living on site. You’re just a ten-minute drive to Bowral and Mittagong here, and yet you’ll get to wake to the sounds of nature and views of the bush.

Your little pad is full of character, with a rustic red corrugated exterior and open-plan living space inside. Gather around the slow combustion fire if it’s cool outside, or grab your coat, open the double French doors and potter out to the covered alfresco area to drink in the surroundings along with a cheeky glass of Southern Highlands wine.

Love the sound of a group vacay in a pad with a mega entertaining deck and a hot tub with enough space for the whole crew to hang? Us too! Oak & Ember House is a four-bedroom Southern Highlands stay that gives good stuff like two fireplaces and a lovely garden to wander, all within a 15-minute stroll of the village centre.

Take to the living area and you can look out over the 1200 sqm garden through the soaring glass windows. The modern kitchen has a heap of space for prepping that group feast, with a benchtop with bar stools where your mates can sip on a G&T while the veggie-chopping gets done.

Later, we reckon you’ll be heading to the ‘Whiskey Room’, a cosy space with a fireplace and vintage charm that makes it perfect for a nightcap. There’s also a sunken fire pit outside where you can gather to toast some s’mores.

Welcome to your very own fairytale cottage just footsteps from Bowral’s boutique shopping and dining destinations. The Croft is a restored four-bedroom stone home that offers a character-filled stay for large groups in NSW. It’s the kind of spot where you could cosy away a winter’s day, before heading out with the team for a spot of wine tasting or a delicious roast dinner. 

The large living space at this Southern Highlands Airbnb is a real highlight, with its feature fireplace and huge lounge that just calls for group chats. But you’re spoilt for choice as there’s also a separate family room, with a 65-inch Samsung Smart TV, James Lane oversized sofa, and wood heater (matches, kindling and quality local hardwood supplied). Cuppa anyone? An adorable touch at this pad is the full tea service set for eight guests, with china teacups and afternoon tea stands. A silver tea service and other items can also be provided on request. Adorbs.

Set on 50 private acres in Kangaroo Valley, Cally Mill Farm is a designer farmhouse retreat where rugged escarpments meet refined, contemporary living. Rebuilt after the 2020 bushfires, the home was thoughtfully reimagined to capture sweeping valley views from every room, creating a stay that feels both grounded in nature and quietly luxurious.

Sleeping eight guests across four king bedrooms (each with its own ensuite) this NSW farm stay is ideal for families, group getaways or milestone celebrations. The open-plan living space features soaring ceilings, a stone fireplace and floor-to-ceiling windows, while a mezzanine lounge and separate media room offer extra space to unwind. Outside, wide wraparound verandahs, a firepit and an outdoor bath beneath star-filled skies set the scene for slow mornings and golden-hour drinks.

Expect a chef’s kitchen with butler’s pantry, beautifully curated interiors and thoughtful architectural details throughout. Beyond the house, rolling paddocks, dams and abundant wildlife complete the experience—think kangaroos at dawn, wombats at dusk and parrots in the treetops.

With space for up to ten, this architecturally designed retreat looks like a Grand Designs masterpiece—and it is perfect for a luxe group getaway in the Southern Highlands.

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 barbecue area with a fire pit, and a master suite complete with a deep stone bathtub for pure relaxation.

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 the Southern Highlands attractions nearby.

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. 

Some tiny homes just give you something a little bit extra—and this one-bedroom Southern Highlands stay is a pint-sized pad with serious appeal. First up, let’s talk stargazing. It’s practically mandatory at this Berrima Airbnb because there’s a whopping four skylights above the King-sized bed. There’s an actual observatory loft at this place too—it’s reached via a ladder, and has a tempting sheepskin beanbag for cosying up under the night sky.

Your accommodation was handbuilt over three years and offers off-grid living while conveniently being just eight minutes from Berrima’s bakeries and cafes. Inside, it’s all Blackbutt timber and handforged steel, with a full kitchen for whipping up something tasty and a lovely north-facing window seat where you can munch while enjoying the country view.

Prefer to cook alfresco? There’s a barbecue on the covered outdoor deck and a fire pit beyond for marshmallow-toasting. Your hosts supply useful stuff like salt, pepper, oil, vinegars, spices, honey from their farm, and herbs from their garden to make feast-time even tastier.

Love a tiny home vibe but fancy a bit more, well, space? You’re not alone and this fab pad on the Southern Highlands’ Sylvan Glen Estate has you sorted. Miniature living has been positively super-sized here, meaning you get 72 sqm of living space (which is bigger than a heap of Sydney apartments, let's be honest). 

The place is light and bright, with big windows and an even bigger personality. The full-sized kitchen has enough stuff to whip up more than just a cheese platter; you can snooze in a king-size bed and roam around your 16 sqm ensuite no trouble. Add in the wood-fired outdoor bathtub and barbecue on the sun deck overlooking the estate’s 7th fairway and we reckon you’ll be in seventh heaven.

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.

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.

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.

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.

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. 

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.