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

Home in Sutton Forest

4.89 out of 5 average rating, 160 reviews

Cashel Vineyard - A Southern Highlands Escape

Nestled on the top of a hill, Cashel Vineyard overlooks the beautiful valleys of the Southern Highlands. This Sutton Forest home has 5 bedrooms with bullnose verandah where you can sit in the warmth of the sun and look over the vineyard. With 2 large living spaces and a modern country kitchen, this 5-acre property is perfect for hosting friends and family getaways. Only 90mins from Sydney, Cashel Vineyard is a short drive off the Hume Motorway and close to Moss Vale (10mins) and Bowral (15mins).

Guest favourite

Guest house in Collector

4.91 out of 5 average rating, 219 reviews

The Flower Shed

Welcome to The Flower Shed. A small magical space in Collector, NSW only 2 minutes off the Federal Highway. The Shed is adjacent to the main house, but is very private. Comfy Sofa bed/couch. We have thought of everything you need for an overnight stay or 2. There is a practical kitchenette for you including a fridge, toaster, electric cooktop, microwave and kettle. Relax and enjoy. Double insulation and reverse cycle air conditioner for cosy Winter nights or cool Summer days. No cats allowed.

Guest favourite

Cabin in Kangaroo Valley

4.82 out of 5 average rating, 594 reviews

Breathe again, Cabin cuteness, entire cottage

This is a little piece of heaven, a moment for some tranquillity nestled within the Kangaroo Valley Golf Retreat located on the Golf Course. A short stroll to the pool. Volleyball. court all walking distance. 2 new tennis courts Walking distance to volleyball court, Giant chess set Badminton court & Swimming pool. Dive in. Quality inclusions. We are 4km from town. Single nite stays please bring own linen, we will supply all towels doonas, blankets, bath mat flannels etc. Queen bed.

Guest favourite

Guest suite in Kangaroo Valley

4.97 out of 5 average rating, 223 reviews

The Captain’s Cabin

Nestled in our citrus and nut orchard is the 'Captain's Cabin'. A hideaway in your own private section of the garden, with an amazing outdoor bath, ample cooking facilities inside and out, and fire pit, not to mention a comfortable queen bed with natural linen and towels, it's your base for the perfect Kangaroo Valley escape. A 5 minute walk from the village centre and 50m from the cycle and walking path, it's the perfect location too. Coffee machine, record player and provisions included.

Top guest favourite

Home in Moss Vale

4.99 out of 5 average rating, 113 reviews

Completely Renovated, Cosy Home

A Beautifully styled, newly renovated home with the assurance of cleanliness and comfort. Your family will be close to everything when you stay at this centrally located home. All amenities and essentials are provided with 'Hampton' styled interior finishes and an eye for detail. Just a short walk to the town centre and a short drive to Nearby Wineries and Wedding Venues. All bed linen and bath towels provided, Smart TV's and complimentary WiFi make this property a very enjoyable stay.

Guest favourite

Home in Berrara

4.94 out of 5 average rating, 157 reviews

Berrara Luxury Retreat Stay 2 nights get 1 free

Free night ends 30th August 2025 Berrara Retreat is the ultimate private getaway- close to great beaches and National Parks. You’ll love my place because of the overall level of spaciousness, quality, comfort and superb indoor and outdoor entertaining options. Very private front to back. In ground pool, remote lock up garage. Top quality kitchen and appliances for the Master Chef or just special family occasions. Has three separate TV viewing areas and NBN for streaming or WFH.

Top guest favourite

Tiny home in Burradoo

4.91 out of 5 average rating, 164 reviews

Highlands getaway

A completely self contained cottage surrounded by beautiful gardens. There is a pool on the property which guests may use. The cottage is in a beautiful leafy suburb of Bowral containing interesting shops , walks, cycling tracks. There are numerous places of interest in the surrounding towns and villages . There is also a fully self contained 2 bedroom aprt(1 queen bed and 1 single bed) on the property . See listing Luxurious Hideaway in BOWRAL airbnb.com./rooms/17128739

Guest favourite

Home in Kangaroo Valley

4.93 out of 5 average rating, 274 reviews

SkyView Villa - WOW Views & Comfort

Set on 150 acres of manicured rolling green hills, SkyView enjoys arguably the best views in a country resort with sweeping views over lakes, glades and the lush green golf course. Ideal for families and couples alike, beautifully appointed and comfortable. Skyview Villa has the Aspire range of mattresses from Sealy Posturepedic, thus ensuring guests the best possible night's sleep. Skyview villa offers free WiFi, plus Netflix & Austar via two 65 inch smart TV's.

Guest favourite

Villa in Kangaroo Valley

5 out of 5 average rating, 43 reviews

Willow at Barranca - Luxury Villa

Willow is a luxury 4 bedroom + 2 bathroom villa that sleeps up to 8 guests. It has been carefully designed for your enjoyment, comfort and relaxation. barranca in Kangaroo Valley is an exclusive retreat offering luxury accommodation for the discerning traveller. Set on 1,000 acres in a rural paradise framed by an amazing amphitheatre of sandstone escarpments that enclose a lush river valley, rich and diverse with wildlife and glorious temperate rain forests.

Top guest favourite

Guest suite in Mittagong

4.93 out of 5 average rating, 893 reviews

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.

Superhost

Home in Welby

4.92 out of 5 average rating, 224 reviews

A Cheerful 3 Bedroom, Newly Renovated Cottage

A cheerful 3 bedroom, newly renovated, and self-contained cottage awaits! Nestled in the heart of the stunning Southern Highlands, within minutes of the regions best restaurants, wineries and cafes. Take a 10 minute walk to Artemis Wines or enjoy nature and the beautiful views along the Boxvale Bush Track just a short walk from your stay. The Town Centre is under 2km away with access to local shops, Woolworths and Boutiques.

Guest favourite

Home in Moss Vale

4.9 out of 5 average rating, 315 reviews

2 Bedroom Newly Renovated Cottage

Newly renovated 2-bedroom cottage situated in the heart of Moss Vale, Southern Highlands. Offering two bedrooms, including one queen & one double, cosy living area, separate designated work space/snug, newly renovated kitchen and laundry space. Outside you will find a large deck showcasing an outdoor entertainment area with a four person spa, fire pit and barbeque.