19 Of The Best Stays In The Southern Highlands For An Epic Weekender

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).

Your accommodation at 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) which is always a win.

This adorable converted garden shed is a top accommodation spot for a couple looking for a cosy weekend getaway in the Southern Highlands.

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.

This ultra-charming guesthouse is a converted stable on the grounds of the 120-acre heritage-listed 1860s Boscobel homestead. At this Southern Highlands accommodation you'll be surrounded by sweeping paddocks, friendly horses, spring-fed dams and historic estate buildings so prepare to get the phone out for some Insta snaps.

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 for soaking in come sunset.

Channel all your Yellowstone-inspired dreams at this special two-bedroom farm stay in Exeter. It might look like a traditional barn, but at this Southern Highlands Airbnb 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.

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 at this Airbnb, as well as other local attractions like Cherry Tree Walk and (for warmer months) the local swimming pool.

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.

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. 

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.

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.