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Bespoke Highlands Cabin

Newly refurbished self-contained cabin combining the beauty of country with the comforts of town. Enjoy trees, abundant bird life, cosy fireplace, luxurious king bed, kitchenette, bath and tv. Exclusive use tennis court; Bowral's best walks at your doorstep; and 5 min drive to fine restaurants, pubs and great shopping. Easy access to Milton Park; Bong Bong Racecourse; Ngununggula Regional Art Gallery; Bradman Museum and Corbett Gardens. Private, cosy and beautiful, it's Bowral's hidden gem.

Romantic hideaway at HAMPDEN HOUSE

This magnificent country home provides a blessed setting for an unforgettable Kangaroo Valley experience .The comforts of modern country living with all the charm of yesteryear .Your own private POOL,sun dried linen wood fire ,treats of French bubbly and locally handmade chocolates await you .WiFi,coffee machine ,three acres of gardens and lawns,RIVER FRONTAGE .Hampden House is only a 10 min stroll or bike ride to the village and get remains a peaceful little world of its own. PID-STRA-589

Cloud Pad – Mountain Retreat at CloudFarm

Welcome to Cloudfarm Cloudfarm is a unique 33-acre sanctuary perched at the highest point of the Illawarra escarpment, offering breathtaking, ever-changing views — where the sky feels close enough to touch. A world away, yet just 7 minutes from Robertson and 25 minutes from Bowral and Moss Vale, it’s the perfect base for a romantic escape or a slow meander through the Southern Highlands — with its cool-climate vineyards, farm gate produce, misty trails, and a touch of chic country charm.

Fantoosh

Welcome to your blissful getaway! This beautifully designed picture-perfect cottage is nestled in the heart of Sutton Forest, the ideal fit for anyone looking to relax and unwind. Enjoy the heated floors and an Internal fire at the press of a button. Firepit outside awaits, sizzle a steak or toast marshmallows under the stars. Snuggle up on the couch, stream a movie you never got to see or work on the super fast internet. Take a walk along the country lanes and enjoy the fresh air.

Arborea Country House 14 - 16 large groups

Arborea Country house is a affordable house with a touch of modern chick decor. All bookings receive a complimentary breakfast. Located only 2 minutes drive from Bowral. Catering for large groups, weddings and conference’s Venues close by: Close to: Milton Park, Centennial Wines, Bowral Golf Club, Bradman Museum, Bendooley Bong Bong race course, and Local Wineries. Just across the road from apartment is large playing fields and views of Mt Gibraltar.

Southern Highlands Get-a-Way —Breakfast Supplies—

A pet friendly, comfortable and well-appointed, self-contained apartment for rent amongst the gum trees. Only a short walk to Mittagong train station, Sturt Gallery, shops, restaurants and galleries. Newly renovated, the apartment has reverse cycle air-conditioner, a private entrance, designated parking area and a private outdoor outlook. Wi-fi and Netflix all included. Comfortable, private, quiet get-a-away so stay a week or more. No cleaning fee.

The Little House - Pet friendly*/Mid-week special!

While 'house' might be a stretch for this cosy studio-style room, it does have separate facilities. There's a separate "kitchenette", shower and toilet. IT HAS ONE KING SIZE BED and ONE SOFABED. The sofabed is charged at an additional $20/night. The Little House has everything you need for a short stay in The Highlands! * The property welcomes gentle, well socialised pups. The Little House backyard is also shared by my super friendly dog and ewe!

Burradoo Loft with King size bed.

Down a lovely tree lined drive, sitting on one acre, a beautiful loft apartment awaits you. Fully self contained with its own entrance, this space has the feel of an art gallery. As the apartment is upstairs, this property is not suitable for people with restricted mobility. Property not suitable for children under 12 years. Unfortunately we cannot welcome pets. 2km to the cafes and shops of Bowral. Bed configuration other than King by request.

woodland retreat - guest studio

A chic space with Mt Gibralter as your backdrop, set in a garden full of birdlife and the occasional wallaby. We offer private accommodation, own entry through a shared garden, sitting room with a good selection of books and mags, Wifi and Bluetooth, kitchenette with a dining space, 2 bedrooms and 1 bathroom. Very close to main wedding venues eg Bendooley Estate and Centennial Vineyards. Walking distance to Bowral, and close to Mittagong .

The Tailor's Terrace | Valley Views & Fire Pit

A beautifully designed architect home with sweeping escarpment views, rated 4.98 stars by 200+ guests and an Airbnb Guest Favourite. Sleeps 5 across 2 bedrooms – each with a private ensuite – plus a third bathroom, fire pit, BBQ deck, and a backyard where kangaroos visit daily. 81 Mbps WiFi and a dedicated workspace included. 100m to the village. Community pool across the road. Can be booked with The Tailor's Cottage for up to 7 guests.

♥️ Jens B&B ♥️

Enjoy easy access to the popular shops and restaurants that this charming place has to offer. Jen's B&B is a 6 minutes drive to the heart of Bowral and just a 90 minute drive south-west of Sydney, perfect for a beautiful weekend away in the country. Bowral is the largest town in the Southern Highlands which is widely known for its exciting and eclectic mix of eateries, wineries, boutique shops, country markets & vintage Antique stores.

The Villa @ The Vale Penrose

Set on five acres of beautifully landscaped grounds in the Southern Highlands, The Villa @ The Vale Penrose is a refined country escape designed for couples seeking space, privacy, and understated luxury. Part of The Vale Penrose—an established boutique farm stay welcoming guests since 2019—the Villa offers a balance of contemporary design and rural tranquillity, with expansive interiors and uninterrupted views over rolling hills.