Guesthouse holiday rentals in Southern Highlands

A modern cabin features a wooden exterior set among tall, lush trees. A spacious deck with outdoor seating is visible, complemented by a barbecue grill nearby. A path of stepping stones leads through a grassy area to the entrance, enhancing a connection with nature.

4.98 out of 5 average rating, 248 reviews

Bespoke Highlands Cabin

Newly refurbished self-contained cabin combining the beauty of country with the comforts of town. Enjoy trees, abundant bird life, cosy fireplace, luxurious king bed, kitchenette, bath and tv. Exclusive use tennis court; Bowral's best walks at your doorstep; and 5 min drive to fine restaurants, pubs and great shopping. Easy access to Milton Park; Bong Bong Racecourse; Ngununggula Regional Art Gallery; Bradman Museum and Corbett Gardens. Private, cosy and beautiful, it's Bowral's hidden gem.

4.98 out of 5 average rating, 122 reviews

Kiamala Cottage

Nestled in the heart of picturesque Burradoo, Kiamala Cottage is located on the property of a cherished 19th-century Southern Highlands homestead. This charming property exudes timeless elegance, offering guests the opportunity to embrace its historic charm and refined living. The beautifully presented cottage is surrounded by meticulously landscaped gardens and a thoughtfully designed sitting area. A striking outdoor fireplace invites aperitivo by the fire, soaking in the serene outdoor space.

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.

Guesthouse in High Range

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.

4.96 out of 5 average rating, 111 reviews

Guest favourite

The exterior of the guesthouse is showcased, featuring light green siding, double barn-style doors, and two small windows. A wall-mounted light is positioned above the entrance. Neatly trimmed shrubs line the base, and a clear blue sky enhances the serene setting.

4.92 out of 5 average rating, 435 reviews

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.

A contemporary two-bedroom guest wing features a warm wooden exterior, complemented by large windows. A pathway leads through a landscaped garden, framed by lush greenery. Sunlight casts a soft glow on the façade, highlighting the modern design and tranquil surroundings.

4.98 out of 5 average rating, 182 reviews

Contemporary Rural Luxury in Lush Garden

Nestled on the edge of beautiful Bowral, this contemporary two-bedroom space is your idyllic escape. Enjoy modern amenities, including an EV charger, in our stylish and sunny self-contained Guest Wing. Your backyard? Step out onto stunning walking trails in Mansfield Reserve and immerse yourself in nature's serenity. And you're just a 10-minute drive from Bowral's vibrant cafes and shops. This property offers the perfect blend of rural tranquillity and urban convenience.

A lush garden path is flanked by vibrant pink flowering trees, leading through a well-maintained landscape. Green grass and neatly trimmed hedges create an inviting space surrounded by various plants and trees, providing a serene natural environment.

5.0 out of 5 average rating, 485 reviews

Buskers End

This cottage is nestled in a breathtaking 2.5 acre established garden. It is perfect for couples wanting to retreat from the world or it is close to Bowral and surrounding attractions including golf clubs and vineyards. The cottage is well appointed with all necessities, such as tea, coffee and toiletries. Large bathroom with spa bath and separate shower. Fully equipped kitchen Wifi Gas fire Air conditioning We would love you to wander and enjoy this beautiful property.

Guest favourite

The cottage exterior is framed by an array of seasonal foliage, with vibrant autumn leaves scattered across the gravel pathway. Potted plants line the entrance, adding a welcoming touch to the white brick facade and large windows that bring in natural light.

4.96 out of 5 average rating, 286 reviews

Coppins Cottage - Your Southern Highlands Stay

A cosy cottage perfect for a weekend away. The cottage sleeps four people but more comfortably two and is separate to the main house, perfectly set up for your privacy. We are walking distance from Bowral centre and a 10-15 minute drive to all the wineries the Southern Highlands has to offer. We are here to make your weekend one to remember, indulge in our cosy cottage, sit back and watch TV and have a glass of wine from your complimentary bottle of wine on arrival.

4.93 out of 5 average rating, 1004 reviews

The cottage features a welcoming facade with a gabled roof and a covered entryway. Lush greenery surrounds the entrance, providing a natural setting. A gravel driveway leads up to the front door, enhancing the inviting atmosphere of this tranquil retreat.

Guesthouse in Mittagong

Alpha Cottage - Mittagong Escape

This cosy cottage provides comfortable and private accommodation. Perfect for an escape to the Southern Highlands. Enjoy a fully self-contained private stay overlooking rural scenery. This cottage has full amenities including cooking facilities, television, heating and under cover parking. An ideal base from which to explore the Southern Highlands. About a 3 minute drive into town and only 7 minutes to Bowral.

A charming exterior is shown, characterized by a blend of brick and paneling. Flower beds with rose bushes are visible in the front yard, adding a touch of color. A spacious driveway leads up to a three-car garage, with trees and greenery surrounding the property.

4.89 out of 5 average rating, 102 reviews

Tudor-style Bowral studio

Welcome to our charming studio flat, nestled in a tranquil corner of Bowral. Enjoy the peaceful ambiance, fresh air and country living, all while being a five-minute drive or, if you’re feeling energetic, a thirty-minute walk from local cafes and shops. Set behind the free-standing garage, on the same property as our home. A new build completed in 2023, with modern amenities.

Guesthouse in Sutton Forest

A large, mature tree provides shade beside a rustic stone wall, which curves along the landscape. Lush green grass covers the ground, and soft sunlight illuminates the scene, highlighting the textures of the tree bark and the stone wall.

Kate’s Cottage with spectacular countryside views

Peaceful studio cottage adjacent to the homestead, with scenic country views on a tranquil 20-acre property featuring treelined walks and stunning drystone walls. Enjoy alfresco cooking under a covered outdoor BBQ area. Just minutes from Moss Vale (6.3 km) and Sutton Forest (5.6 km), this charming retreat on beautiful Oldbury Road is perfect for a relaxing country escape.

4.96 out of 5 average rating, 214 reviews

The studio is framed by vibrant flowering plants, with a path leading to a wooden deck. White patio chairs are positioned outside, inviting relaxation. Soft light filters through lush greenery, enhancing the serene garden setting.

4.97 out of 5 average rating, 432 reviews

The Shed @ Bowral

The Shed @ Bowral is a very comfortable and cosy industrial style studio with lovely garden views and a ‘cool’ private semi enclosed verandah area. Quiet and peaceful location close to the town centre and across the road from the Cherry Tree walking/bike path. The accomodation is an easy 15 minute walk to Bowral town centre and the train station.

A spacious studio layout features a plush bed with layered bedding, positioned near glass doors leading to a deck. A dining table with chairs is visible, along with a comfortable armchair. Natural wood flooring and beams enhance the inviting, modern décor.