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Holiday rentals in Wollondilly River

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Top-rated holiday rentals in Wollondilly River

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite
Tiny home in Razorback
4.99 out of 5 average rating, 291 reviews

Razor Ridge Retreat-Tiny House- Pet Friendly-Views

PET FRIENDLY!!! "RAZOR RIDGE RETREAT" / "A LITTLE SLICE OF AUSTRIA" is the first of its kind in the Razorback area. It's a cosy, luxury "Tiny House" located in an idyllic bush setting on a 5 acre property in the Razorback ranges, about an hour's drive from Sydney. The tiny house is nestled safely on the edge of a ridge where day & night, spectacular uninterrupted views to the Sydney skyline can be enjoyed by you with magical sunrises and sunsets seen from your bed and also the wild birdlife.

Top guest favourite
A modern gray structure is set against green pastures and distant hills. Large windows reflect natural light and provide views of the surrounding landscape. A wooden deck leads to a lawn area, featuring a firepit and seating, ideal for outdoor relaxation.
Cottage in Gerringong
4.93 out of 5 average rating, 544 reviews

Infinity on Willowvale

Gorgeous boutique stay in Gerringong. Custom-built for a couple, Infinity on Willowvale has a king-size bed, bath for two, private firepit, and a huge deck to take in the views and sunsets. Everything is designed for relaxation. Infinity is set among the rolling green hills on the idyllic Willowvale Road, which boasts dairy farms and the stunning Crooked River Winery. Ten minutes to Kiama and Berry on the NSW South Coast. Just 5 minutes from the beach, you'll feel a million miles from anywhere.

Guest favourite
A tiny house positioned on a grassy area, featuring a large undercover deck with several outdoor chairs. Dense trees provide a natural backdrop, creating a sense of privacy amid the bushland. The structure is designed with a modern aesthetic, blending into the tranquil surroundings.
Tiny home in Tallong
4.93 out of 5 average rating, 346 reviews

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!

Top guest favourite
A scenic view captures a sunset over rolling mountains, with a foreground of lush greenery. Lavender and other plants are visible, providing texture to the landscape. The sky is filled with soft clouds reflecting warm hues, creating a serene backdrop to the natural setting.
Guest house in High Range
4.98 out of 5 average rating, 101 reviews

Farm stay at Melaleuca cottage

Escape to our cozy cottage on a 100-acre farm, where mountain views greet you at every turn. Cool off in the plunge pool or soak in the wood-fired hot tub under open skies. As the sun sets, gather around the fire pit and enjoy the tranquility of the starlit night. Surrounded by Nattai National Park, you’ll be immersed in nature – with birdsong, fresh air, and stunning scenery. Whether you're after adventure or a peaceful retreat, this setting offers the perfect blend of comfort and relaxation.

Top guest favourite
A tiny house with a wooden deck is nestled among towering gum trees. The exterior features a combination of dark wood and modern metal panels. Large windows provide natural light, creating an inviting connection to the surrounding nature.
Tiny home in Collector
4.98 out of 5 average rating, 196 reviews

Enough | Good

Enjoy a unique Tiny House that was designed and built on this very farm. "Dovolj | Dobro" is annexed off our 3acre Selah Gardens, which you will have access to. Nestled amongst gum trees overlooking a large dam, it is surrounded by native wildlife and grazing stock. A unique feature of this location is a walking track through our working farm to The Olive View Restaurant, with great food and amazing coffee. In keeping with minimum impact on the environment, it contains a composting toilet.

Top guest favourite
Two individuals sit in chairs around an outdoor fire pit, with flickering flames providing warmth and light. A small table holds flowers, surrounded by a backdrop of dense trees and foliage, creating an intimate atmosphere in the evening setting.
Cabin in Sutton Forest
4.95 out of 5 average rating, 156 reviews

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)

Top guest favourite
A light-filled nook features a spacious bed with multiple pillows and a soft throw, designed for comfort. Large windows frame the stunning views of rolling hills, allowing natural light to illuminate the cozy space. Wood accents complement the inviting atmosphere.
Tiny home in Blakney Creek
4.98 out of 5 average rating, 194 reviews

The Barlow Tiny House

Nestled in the middle of a working cattle and horse farm in the Yass Valley, The Barlow Tiny House is the ideal place to relax, unwind and reconnect with nature. Enjoy this Tiny House in the countryside that makes a big statement. Enjoy breakfast inside or out, with surrounding views of the rolling hills.Take a wander and explore, and discover our kangaroo and wombat neighbours.If you are interested, we can provide recommendations on the best walks in the area, suitable for all abilities.

Superhost
A serene indoor scene features two guests engaged in a game of chess on a bed adorned with neutral-toned linens. Large windows frame views of the lush rainforest outside, allowing natural light to brighten the wooden interior.
Tiny home in Foxground
4.85 out of 5 average rating, 454 reviews

Creek side Tiny House in a sub-tropical rainforest

Located creekside in a rainforest our Escape Pod (tiny house) is in one of the most beautiful locations the region has to offer. You will feel your worries ebb away while you listen to the natural surrounds, or your fave tunes. What you get up to during the day is totally up to you, go hiking, explore the local beaches, shops, cafés and eateries or simply sit by the fire with a good book and be alone with your thoughts! Your off-grid venture awaits – This is not your normal hotel stay!!

Top guest favourite
A rustic cottage is framed by lush greenery, showcasing weathered wooden siding and a metal roof. Large windows invite natural light, while a small seating area and barbeque are positioned on the front deck. Surrounding gardens feature a variety of ornamental plants.
Cottage in Jamberoo
4.98 out of 5 average rating, 380 reviews

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 .

Top guest favourite
A luxury outdoor spa is shown against a vibrant sunset backdrop. The round spa features an inviting whirlpool, with serene green fields and scattered trees visible in the distance.
Villa in Penrose
4.99 out of 5 average rating, 328 reviews

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.

Superhost
The cabin is positioned on a grassy area, surrounded by tall trees. Large bi-fold doors open to a private deck, with steps leading to an inviting entrance. The exterior features a mix of natural and metal textures, creating a blend of rustic and modern elements.
Tiny home in Exeter
4.85 out of 5 average rating, 215 reviews

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).

Top guest favourite
An aerial view showcases a modern retreat featuring a striking combination of dark and warm exterior tones. The outdoor area includes a seating space near a firepit, with landscaping enhancing the natural surroundings. A deck extends from the side, integrating outdoor living with the serene setting.
Tiny home in Penrose
4.99 out of 5 average rating, 136 reviews

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.

Popular amenities for Wollondilly River holiday rentals