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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.

Wollemi House - in forest and waterways with pool

Escape to your private oasis nestled among beautiful trees and surrounded by breathtaking natural scenery in the Southern Highlands of Robertson. This gorgeous property sits on a sprawling acre of land with a rare Wollemi pine tree in the backyard and a serene creek that winds through the property. With its pool and deck, this tranquil retreat is the perfect place to kick back and relax on warmer days. And when the nights turn chilly, cozy up by the fire pit and gaze up at the stars above.

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.

WATERSHED - Robertson

Welcoming country chic interiors with all the mod cons. You will enjoy luxury finishes in this converted machinery shed. Fully insulated, with double glazed windows & doors. There is a wood fire & heaters. The shed is 80+ metres away from the 1880s farmhouse where we live & so you are far enough way to feel that you have the property to yourselves. There are dogs, alpacas, sheep. A wonderful farm stay property, a walk away into Robertson or a very short drive. @watershedrobertson

Falls Cottage, in the rainforest at Jamberoo

Falls Cottage was built by a Jamberoo local in the 1980s and has grown in charm and character with every passing year. We have lovingly restored it with a country cottage kitchen, hand crafted interior finishes, a comfortable mezzanine bedroom and a deck and barbeque area to maximise guests’ enjoyment of the beautiful rainforest surrounds. We now have an EV charging station on the property . Type 2 , up to 22 KW an hr. Costs apply .

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.

ARUNA Estate off-grid cabins

ARUNA Cabins provide the ultimate off-grid experience. Nestled amongst the Australian Scribbly Gums, it offers a bush view, down to the River. If you want to get as far as possible from the bustling world, the ARUNA cabin is for you. Custom built for their bush location, our cabins provide a stylish and snug escape. They are completely off grid so you can ensure your total freedom from the everyday.

The Hideaway at Sylvan Glen Estate

Romantic couples retreat | Outdoor bath | Southern Highlands escape Escape to your own private retreat in the Southern Highlands. Wake up to birdsong, soak in the outdoor bath under the stars, and spend cozy evenings by the fire pit overlooking the countryside. Less than two hours from Sydney and Canberra, it’s the perfect countryside getaway for a romantic weekend, anniversary or relaxing escape.

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, full laundry and a backyard. 81 Mbps WiFi. 100m to the village. Community pool across the road. Can be booked with The Tailor's Cottage for up to 7 guests.

Spiral House – Mountain Hideaway for Two

Spiral House at CloudFarm is a beautifully designed round house made for two—a romantic, private hideaway perched on the highest point of the Illawarra escarpment. Completely surrounded by forest and sky, it’s made for slowing down and remembering what matters. Wake to mountain-to-sea views, soak in the open-air tub, and let the quiet—broken only by birdsong—do its work.

Berry Farm House

Forget your worries in this spacious 1900’s country cottage, lovingly restored amongst manicured gardens by two artists, interiors are a combination of collected treasures and vintage finds, the farm cottage is set on sprawling gardens to a lake of a private 16 acre farm located only 4 mins drive to Berry town and 5mins to the ocean, Berrys Bay / Seven Mile Beach.

Berry Cottage Escape. Beach, Wineries & Village

Escape to our 2-bedroom sandstone cottage on 3 acres of award-winning gardens, just 1 km from Seven Mile Beach and 6 km from Berry Village. Perfect for couples or families, with stunning north-facing views, cosy interiors and thoughtful touches throughout. Relax by the fire pit in winter, enjoy breezy summer days, and explore nearby wineries, walks, and beaches.