House holiday rentals in Southern Highlands

The exterior of the retreat showcases a brick facade with large windows framed by dark shutters. Lush green hedges line the walkway, leading to a set of stairs that ascend to the entrance. A vibrant garden complements the home's charming appearance.

4.99 out of 5 average rating, 106 reviews

The Cricket House - Family & Pet-Friendly Home

This charming dog-friendly 4-bedroom retreat is in the heart of Bowral, NSW in the picturesque Southern Highlands. Our lovely light-filled home offers a perfect blend of modern comfort and elegance featuring four lovely, spacious bedrooms, three living areas and a fully equipped kitchen perfect for preparing delicious meals to be enjoyed in the stylish dining areas. With its central location, our home is a stone's throw away from Bowral's lovely cafes, boutique shops, and cultural attractions.

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4.99 out of 5 average rating, 153 reviews

The Cottage: luxury & Heritage in Bowral's heart

Immerse yourself in the quintessential Bowral lifestyle. 'THE COTTAGE' combines historic elegance & charm with custom curated equine themed luxury decor brands, positioned perfectly for those attending weddings, exploring 'Tulip Time' or seeking a sophisticated village haven. This spacious & cosy 3 bedroom home accommodates 6 guests in the exclusive high-end 'old Bowral', featuring a ready-to-light fireplace, a large entertaining deck & a quiet, tranquil tree-lined central location to the CBD

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4.98 out of 5 average rating, 104 reviews

A cozy lounge area features a clear glass coffee table positioned in front of a cream-colored sofa. Two large windows offer views of greenery, allowing natural light to brighten the space. A collection of flowers and candles adorns the table, while a soft throw blanket rests on an armchair.

Home in Berrima

Clanoc Cottage a cosy, rustic, Highlands Retreat

Welcome to Clanoc Cottage a 5-minute stroll from the heart of Berrima Village. An ideal base for couples, friends, or families wanting to relax, explore, and enjoy the charm of historic Berrima and the Southern Highlands. The cottage features two Queen beds and a King Single with trundle—each made up with lovely linen and electric blankets for cosy comfort. Enjoy a brand-new bathroom, a well-equipped kitchen perfect for cooking and entertaining, & a spacious yard ideal for relaxing outdoors.

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4.91 out of 5 average rating, 128 reviews

The cottage exterior features a dark blue facade with white French doors opening onto a wooden deck. Two Adirondack chairs are positioned outside, surrounded by neatly arranged shrubs and gravel landscaping with decorative stones.

Home in Moss Vale

Cottage on Kings

Cottage on Kings is situated on Moss Vale's premiere street. A short stroll to cafes, bars, homewares and fashion boutiques and 2kms to The Briars, the highlands most popular country pub. A one bedroom cottage with seperate living area, kitchenette and large deck overlooking a beautiful oak tree. Luxe Queen bed and large linen sofa, cushions, blankets will ensure you relax in comfort. TV in bed or on the lounge. Bluetooth and wifi for streaming music, or your favourite program in peace.

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5.0 out of 5 average rating, 113 reviews

Home in Mittagong

Views, 4/5 queen bedrooms and a boutique vibe

Welcome to BBH - with multiple living spaces, fully equipped kitchen with coffee machine, pool table, ducted heating & fans, north facing and made for relaxing. Lush gardens and private setting, hot tub & firepit. **Please note: For 4 bedrooms/ main house, select up to 8 guests. To book the separate Shack/5th bed, select 9 guests, price will automatically update. Rates includes cleaning and linen. If not booked, Shack remains empty - property is all yours. Licence number PID-STRA-8519

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4.98 out of 5 average rating, 367 reviews

A cozy fire pit area surrounded by lush greenery provides a private outdoor space. Rustic seating made from wood and simple structures frame the scene, inviting relaxation. The backdrop features a stylish bungalow elevated among trees, emphasizing the serene natural environment.

Home in Mount Kembla

'The Bower' Stylish garden bungalow Mount Kembla

'The Bower' is located in lush gardens in the historic village of Mt Kembla. This stylish bungalow is the perfect relaxing retreat or home base to explore the Illawarra and South Coast. Walk to the Historic Mount Kembla Hotel for dinner and a drink or explore the many bush walks located in and around the area. Wake up amongst the trees and end your evenings relaxing on the large deck or around the fire pit. Only fifteen minutes away from Wollongong CBD or beautiful beaches of the area.

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4.98 out of 5 average rating, 232 reviews

A spacious outdoor deck is showcased, featuring a small table with two chairs set for a meal. An expansive view of the Kangaroo Valley escarpment is visible in the background, with the warm hues of sunset casting a serene glow across the landscape.

Home in Kangaroo Valley

The Tailor's Terrace, Kangaroo Valley Village

A beautifully designed architect home with sweeping escarpment views — rated 4.98 stars by 200+ guests and an Airbnb Guest Favourite. Sleeps 6 across 3 bedrooms, each with a private ensuite. Enjoy the fire pit, BBQ deck, laundry and a private backyard, plus fast 81 Mbps WiFi for those who want to stay connected. Travelling with extra little ones? We're happy to accommodate additional children — Room 2 has a single bed, and a porta cot is available on request. Just reach out when booking.

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A charming guest accommodation is visible, featuring weatherboard walls and a pitched roof. Large glass doors provide access to the interior, framed by neatly trimmed hedges and a small garden area. Surrounding greenery contributes to a sense of tranquility.

4.9 out of 5 average rating, 431 reviews

The Potting Shed at Bunya House Bowral

The Potting Shed at Bunya House is a gorgeous purpose built guest accommodation with every amenity covered to make your stay in Bowral an enjoyable one. Positioned overlooking a beautiful vegetable garden designed by the renowned Australian garden designer Paul Bangay, The Potting Shed with it's polished concrete floors, weatherboard walls, king bed and kitchenette with breakfast making facilities is the perfect spot for a mini vacay. Parking on site, and an easy walk to town.

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An airy living space features two cozy armchairs facing a wooden table with a chess set. A large dining table is set to one side, surrounded by black chairs. A staircase leads to the upper level, complemented by rustic decor and large windows allowing natural light.

4.92 out of 5 average rating, 145 reviews

The Coach House at The Rift Estate

Set in rambling heritage-listed gardens at The Rift Estate, The Coach House is an elegant, charming country retreat. Gourmet kitchen, expansive living, dining and relaxed alfresco spaces; minutes to bushwalking trails, wineries and Bowral town. Built at the same time as the grand old late-nineteenth century Italianate mansion nearby, The Coach House once accommodated the coachman and horses and retains many original character features that reflect its rich history.

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4.94 out of 5 average rating, 104 reviews

A two-storey manor is set against a backdrop of tall green trees, with a well-kept garden adorned with a variety of plants. The driveway leads to a detached garage, showcasing a harmonious blend of natural and architectural elements within the outdoor space.

Home in Mittagong

Stunning Highlands Manor-Accommodates 2-12 people

A Quintessential Southern Highlands property on the sunny slopes of Mt Gibraltar. A magnificent two-storey manor, exquisitely furnished, surrounded by picturesque gardens featured in several house & garden magazines over the years. Just moments from the convenience of Bowral & Mittagong town centres, popular wedding venues, wineries and amazing restaurants. Ideal venue for group family/friends get-togethers, wedding stays, golf weekends & the likes

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4.9 out of 5 average rating, 271 reviews

A historic cottage is partially obscured by lush greenery, featuring a classic corrugated iron roof. A well-maintained garden surrounds the property, showcasing established trees and shrubs. The front yard includes a grassy area with a vibrant yellow flowering bush, creating a natural and inviting setting.

Home in Berrima

'Rosevilla' in Berrima.

Built in 1883, this gorgeous historic cottage is right in the heart of Berrima village, within easy walking distance of exceptional restaurants and cafes, quaint local shops, historic buildings, the beautiful river and Australia's oldest continually licensed inn. Bendooley Estate is only a 5-minute drive away, making the cottage an ideal choice for wedding guests. Numerous wineries and Berkelouw Book Barn are all close by.

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A modern kitchen area is showcased, featuring white cabinetry and a marble countertop. Stainless steel appliances, including a refrigerator and stove, are visible. Three wooden bar stools are positioned at the counter, complemented by colorful cushions on a nearby sofa.