Guesthouse holiday rentals in Southern Highlands

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Top-rated Guesthouses in Southern Highlands

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Top Guest favourite
An open living area features large windows that invite natural light. A comfortable pink sofa is complemented by a chic coffee table and cozy decor. A modern entertainment unit is mounted on the wall, while a dining table for two enhances the inviting atmosphere.
Guesthouse in Minnamurra
5 out of 5 average rating, 210 reviews

Harvest Moon Guesthouse-Minnamurra

Welcome to HarvestMoon, our stylish guesthouse and couples retreat built with heart and soul. We completed Harvest in January 2022, so this is a new beginning for ourselves and guests-we look forward to welcoming you! The space is sheltered by our majestic lemon-scented ghost gum, which hosts a variety of birdlife, that you can watch from your own private deck. Do so why your bbq is cooking, or unwind in a bubblebath while watching the stars. HarvestMoon was a finalist for 2023 Host of the Year

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.
Guesthouse in Burradoo
4.93 out of 5 average rating, 378 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.

Top Guest favourite
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.
Guesthouse in Bowral
4.97 out of 5 average rating, 113 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.

Top Guest favourite
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.
Guesthouse in Bowral
5 out of 5 average rating, 429 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.

Top 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.
Guesthouse in Burradoo
4.96 out of 5 average rating, 253 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.

Top Guest favourite
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
4.93 out of 5 average rating, 875 reviews

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.

Superhost
The exterior of Welby Park Manor is framed by lush greenery and blooming flowers. Stone pillars support the covered porch, featuring comfortable seating. The charming roofline and wooden accents highlight the historical character, creating a welcoming first impression for guests.
Guesthouse in Welby
4.84 out of 5 average rating, 769 reviews

The Chapel at Welby Park Manor

Built in the 1870's/80’s, Welby Park Manor is one of the oldest homes in the Highlands. The Chapel is a freestanding sandstone guest cottage with private entry and outdoor area. The property is a two-minute drive from the Mittagong shops, a seven-minute drive to both Bowral and Berrima, and close to local wineries etc. Our guests come here to enjoy the country life in the Chapel of an historical home.

Top Guest favourite
A modern retreat is presented with a sleek corrugated exterior, surrounded by lush greenery. A spacious deck extends from the structure, offering outdoor seating and a cozy gathering area, inviting a connection with nature.
Guesthouse in Jamberoo
4.96 out of 5 average rating, 195 reviews

JACARANDA AT JAMBEROO

Treat yourself to an unforgettable escape. Set in the emerald green countryside just moments from historic Jamberoo, this romantic converted dairy is perfect for couples. Slide open the spacious living areas glass doors and bring the outside in. This relaxed contemporary self contained retreat is tucked into dairy country with a view across a waterlily filled pond, up to the Saddleback escarpment.

Top Guest favourite
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.
Guesthouse in Sutton Forest
4.95 out of 5 average rating, 177 reviews

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.

Top Guest favourite
An ornate black metal gate stands open, framed by stone pillars. Beyond the gate, a gravel driveway leads toward a charming building surrounded by well-kept gardens. A friendly Newfoundland dog is visible at the gate, providing a welcoming presence.
Guesthouse in Bowral
4.92 out of 5 average rating, 154 reviews

The Annexe at Beatrice Park, Bowral

Welcome to The Annexe at Beatrice Park Perfect for Couples or Solo Travelers Nestled within the heritage-listed gardens of Beatrice Park, The Annexe offers a private retreat ideal for a weekend escape or an extended stay. Whether you're here for leisure or business, you’ll find The Annexe a tranquil and comfortable home away from home.

Top Guest favourite
The exterior of the studio displays a modern, dark-toned facade complemented by large windows. A welcoming pathway lined with greenery leads to the front door, framed by well-maintained gardens and tall trees in the background, inviting guests into the serene setting.
Guesthouse in Bowral
4.95 out of 5 average rating, 253 reviews

Sauna Haus with Scandinavian design

The Sauna Haus, completed in October 2021, is situated on a 1 acre property, shared with our residential home. It is perfect for couples and small families wanting to retreat from the world whilst being a short 5 min. drive/15 min. walk to Bowral and surrounding attractions including vineyards, boutiques, cafe's and golf clubs.

Top Guest favourite
The studio is nestled among tall trees, featuring a wooden deck with two chairs and a small table. The light wood finish of the deck contrasts with the natural surroundings. A soft, pink sunset paints the sky in the background, enhancing the tranquil atmosphere.
Guesthouse in Mittagong
4.99 out of 5 average rating, 175 reviews

The Treehouse Studio

Enjoy a peaceful stay at the beautiful Treehouse Studio on Mount Gibraltar, Mittagong. This stand alone guesthouse is located on a tranquil property while still being within walking distance to Mittagong's cafes and restaurants. Located a short drive from Bowral, Berrima and Moss Vale. A perfect weekend getaway for couples.

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