Vacation rentals in Wollondilly River

"Whispering Pines" rural escape

Enjoy a relaxing country escape in our self-contained, 3 bedroom house set amongst mature pine trees. Just 2 hours drive from Sydney, a little over 1 hour from Canberra and 15 minutes north of Goulburn, the split 3-level house is situated on our 65 acre hillside property. A great place to spend time with family and friends, enjoy the fresh air exploring the natural surroundings or stay indoors for a game of pool by the fireplace.Perfect for a short stopover whilst travelling or a longer getaway!

Wildernest "T1" - Off-Grid Wilderness Experience

Looking for an adventure, an escape, or just an opportunity to reconnect with nature? ‘Wildernest’ offers a unique off-grid experience, staying in a tiny house (nicknamed "T1") nestled amongst the bushland on the edge of the Wingello Forest. A perfect sanctuary to relax and rejuvenate. Or as a base for an adventure - bush walking, mountain biking, wildlife spotting - or perhaps exploring the Southern Highlands foodie hot spots is more your thing. Come with friends and book Wildernest "T2" too!

Basil's Folly

Hi I'm Basil. I live with my donkey family on a beautiful property in Exeter. Come and stay in a lovely private barn beside my paddock. It has 2 queen beds, a spacious & warm living area, with a kitchenette and a stylish bathroom. Escape the stresses of the modern world & enjoy the view over the pond. Curl up on the couch in front of the wood fire. Explore the delights of the Southern Highlands-cafes, restaurants, lovely drives and walks. We are only 10mins from beautiful Morton National Park.

Unique'Danglestone' Couples Hideaway in the Forest

Awe inspiring views surrounded by nature. Nestled in the lush greenery of a private forest this modern architecturally designed cabin is luxury at its best. With the warmth of the heated floor & indoor gas fire you will be toasty warm all year round. Sutton Forest is very near several vineyards and villages. An ideal location to escape the city. PETS allowed but please disclose when booking- Max 2 people only (not suitable for infants) 1 Queen bed only MASSAGE available nearby (plse ask)

"The Burrow", Mittagong, Southern Highlands, NSW

“The Burrow” is a self-contained cottage on a 100 acre wildlife sanctuary just 5km from the centre of Mittagong. Once you arrive, it's just you and a few hundred kangaroos and a wombat or two. We invite you to take in nature at your own pace in this peaceful & private setting. “The Burrow” is a hand-built, mud-brick cottage set on the Southern Highlands of NSW. It's quirky yet very comfortable. With nature & wildlife all around we want you to feel like you're 1000 miles from anywhere.

Contemporary Country Experience

Contemporary country experience Enjoy the simplicity and restoration that rural peace offers without getting your hands dirty (*unless you want to!). This design inspired cottage provides a place for up to 6 people to take in the sunset sitting by the open fire, then wake to collect fresh eggs and watch the horses, cows and kangaroos graze, or wander down to the creek for a picnic. The cottage is fully enclosed in a fenced area 800m2. We have changed the fencing so none is electric.

The Stables at Long Paddock

The Stables is a self contained guesthouse situated on our family property in beautiful Burradoo. Suited to either a family of up to four or two couples, the guesthouse is fully equipped for a weekend away in the countryside. Located midway between Bowral and Moss Vale, the Stables is set on 10 picturesque acres and surrounded by unspoilt farmland, with views to Oxley Hill and surrounds - yet Bowral’s boutiques, homewares stores, restaurants and cafes are just 5 minutes away.

Millynn House - Unit 1

Step into a piece of history with this fully renovated apartment nestled within an early 1900s heritage building. Located in the heart of Goulburn, this charming space combines historic charm with modern comforts for an unforgettable stay. Just steps away from local cafes, restaurants, and shops, this apartment provides the perfect base for exploring the town's rich history and vibrant culture. Immerse yourself in the timeless elegance of this beautifully renovated apartment!

The Shack at Bimbimbi in semi rural Exeter.

The Shack at Bimbimbi is well appointed, private, and is situated on 5 acres, 40 meters from the main house separated by gardens. There is a box fire and heating for chilly nights. A great getaway, close to walks in Morton National Park, Bundanoon, Exeter Village and a short drive to Moss Vale and Bowral. A complimentary breakfast hamper is supplied for a minimum 2 night stay, free WiFi. We hope you will come and see for yourself.

Converted Dairy Fitzroy Falls

The Dairy sits within approximately 9 acres of beautiful ,private gardens on a 29 acre property . The one bedroom cottage is light and bright with a small kitchen, a wood burning fire, reverse cycle airconditioning, ceiling fans and gas heating. There is additional accommodation in the Japanese Studio . NOT suitable for children or pets..20 mins to Bowral and Moss Vale Linen provided. Strictly non smoking property. STRA PID -6648

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.

Southern Highlands Vineyard Cabin by Outpost

Welcome to our premium country cabin nestled within the picturesque wineries of the Southern Highlands! Set amongst the vines of Exeter Vineyard & Cellar Door, our cosy, private retreat offers a unique experience where you can unwind, sip local wines, and bask in the breath-taking beauty of the Australian countryside. Please Note: We offer a discounted nightly rate for mid-week bookings (Sun-Thurs).