Family-friendly holiday rentals in Robertson

Luxury Country Escape at Colyersdale Cottage

Set on a 350 acre cattle property 10 minutes from Moss Vale you will find this purpose built, luxurious Hampton’s style cottage. With a 2 car connected garage and indoor/outdoor sandstone fireplace, it comprises 2 large king bedrooms each with a walk-in robe and ensuite. There is ducted air conditioning, fully appointed kitchen, open plan living dining, concealed laundry, outdoor dining terrace, swinging seat and BBQ. Perfect for 2 couples or a family of 4 or 5. Message me for longer stays.

Family · Indoor spaces · Location

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.

Family · Kitchen · Wifi

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.

Kitchen · Family · Decor

Roy's Run Farm Stay.

The comfortable one bedroom cottage is located on our 450 acre working cattle property. We are close to the seaside towns of Shellharbour and Kiama. You can enjoy the beaches and then come home and just sit and gaze at the views of the farm. We have many animals for you to get close to if you desire and an abundance of bird life on the property. The cottage has a comfortable veranda for you to relax and watch the horses and cattle graze. A country experience just 2 hrs drive from Sydney.

Indoor spaces · Family · Long stay

Luxurious,Cosy & Relaxed Apartment with Spa Access

Are you looking for something a little bit special? Located in picturesque Robertson, an easy 20 minute drive from Bowral, ‘Highlands Meadow View’ is a modern spacious light filled 2 bedroom apartment offering guests a luxurious and quiet getaway in a pretty, rural setting. Situated just 2 minutes by car from the main street of Robertson, it is an ideal base if you’re travelling down for a wedding, exploring the Highlands or visiting Kiama and other beautiful parts of the South Coast.

Family · Indoor spaces · Outdoor spaces

Rosewood Cottage - on a working regenerative farm

Renovated 2 bedroom 1930s Cottage, perched on the gentle slopes of a lush 120 acre working regenerative farm, where happy sheep and cows graze on chemical-free pasture. Relaxing, family-friendly, off-grid, with breathtaking views of the beautiful Kangaroo Valley escarpment. Only 4kms from the charming Kangaroo Valley Village and 20min from historic Berry and its nearby beaches. Rosewood Cottage will offer you a comfortable and cosy stay with everything you need for a short getaway.

Family · Kitchen · Location

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

Indoor spaces · Family · Quiet

The Shed at Penrose

Cosy self Contained Apartment on a small 5 acre working horse training property based in Penrose, Southern Highlands NSW Our apartment can accomodate a couple or a family of 4 making it an easy choice for somewhere to stay whilst visiting the beautiful Southern Highlands. Be greeted in the morning by our small family of horses or bring your own horses for a riding holiday, where an accredited coach is also available for lessons and the Penrose forest is on our doorstep.

Family · Indoor spaces · Quiet

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.

Indoor spaces · Family · Pets

The Escarpment Loft / pet friendly

Nestled on an escarpment overlooking the Great Dividing Range, at the top of Macquarie Pass and set amid 14 acres of lush countryside, this two-bedroom contemporary apartment is an ideal rural escape. Whether you're passing through for a night or you’re taking a few days to recharge, you will feel the cares of the world fade away as you drive through the gates and make your way up the winding road to the residence.

Family · Indoor spaces · Decor

Ranelagh Cottage Robertson

Robertson part of the Southern Highlands community is very relaxing and you will not regret recharging your batteries here. Its so peaceful but there are a lot of attractions within a short drive if this is what you are looking for, the township is within easy walking distance and everything within the home has been catered for to ensure you stay is as comfortable as possible.

Kitchen · Indoor spaces · Value

MaddOx Farm Cottage | Farm Stay

Situated in the beautiful countryside of Burrawang in the Southern Highlands. Kick back and relax in this calm, stylish farm stay. This bespoke cottage has been purpose built for your visit. Enjoy the peace and fresh air of the country whilst you overlook the paddocks and dam. Meet the friendly residents - Cows, Alpacas, Goats & Sheep and enjoy a cuddle or feed with them.

Family · Kitchen · Cleanliness