Vacation rentals in Wingecarribee Shire

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Top-rated vacation rentals in Wingecarribee Shire

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Top guest favorite

An outdoor deck features a round table surrounded by four iron chairs. Lush greenery creates a backdrop, with a garden of blooming flowers and mature trees visible in the distance. Natural light brightens the scene, enhancing the peaceful ambiance.

Guest suite in Bowral

5 out of 5 average rating, 244 reviews

Bradman Studio -tranquil garden, easy walk to town

Located in the charming Old Bowral precinct, Bradman Studio is a level, easy 10 min walk (900m) to Bowral's main street and only 100m from picturesque Bradman Cricket Oval. Spacious open layout, abundant natural light and wide views over our mature, very private rear garden. Adjoining deck for outdoor dining, A/C & double glazed windows assure comfort year round. KS bed, heated bathroom floor, beautiful quality bedlinen & well equipped kitchenette.Complimentary snacks/drinks. On-site EV charger.

Top guest favorite

A modern barn stands amid a green landscape, with two donkeys grazing nearby. Large windows reflect the natural light, providing views of the surrounding trees and the tranquil setting. This peaceful scene is framed by the foliage of nearby plants.

Barn in Exeter

5 out of 5 average rating, 103 reviews

Basil's Folly

Hi I'm Basil. I live with my donkey family on a beautiful property in Exeter. Come and stay in a lovely private barn beside my paddock. It has 2 queen beds, a spacious & warm living area, with a kitchenette and a stylish bathroom. Escape the stresses of the modern world & enjoy the view over the pond. Curl up on the couch in front of the wood fire. Explore the delights of the Southern Highlands-cafes, restaurants, lovely drives and walks. We are only 10mins from beautiful Morton National Park.

Top guest favorite

A couple stands closely together in a lush garden, surrounded by vibrant greenery and decorative stone features. In the background, a charming glass structure with a gabled roof is nestled among the trees, contributing to the serene atmosphere of the setting.

Place to stay in Fitzroy Falls

4.99 out of 5 average rating, 575 reviews

Japanese Studio Fitzroy Falls

Relax in our private beautiful Japanese Studio , open plan bedroom and living room with seperate small bathroom. NOT suitable for children or pets. The Studio has a bar fridge , microwave, toaster, coffee pod machine and kettle. No kitchen. .Enjoy stunning 9 acres of gardens . Perfect location for photo shoots, wedding ceremonies or getaway. We also have 'The Dairy' which is a 1 bedroom cottage with a kitchen and fireplace. Strictly Non smoking. All guests to be COVID vaccinated. STRA 6648

Top guest favorite

A Hampton’s style cottage is showcased, surrounded by lush green landscaping. The white exterior features a dark roof and a stone fireplace. A spacious veranda runs along the front, providing shaded areas for relaxation amid the scenic countryside.

Farm stay in Moss Vale

5 out of 5 average rating, 200 reviews

Luxury Country Escape at Colyersdale Cottage

Set on a 350 acre cattle property 10 minutes from Moss Vale you will find this purpose built, luxurious Hampton’s style cottage. With a 2 car connected garage and indoor/outdoor sandstone fireplace, it comprises 2 large king bedrooms each with a walk-in robe and ensuite. There is ducted air conditioning, fully appointed kitchen, open plan living dining, concealed laundry, outdoor dining terrace, swinging seat and BBQ. Perfect for 2 couples or a family of 4 or 5. Message me for longer stays.

Top guest favorite

A guest is seated on a stylish deck, engaging with a book, flanked by two comfortable rattan chairs. Large glass doors provide a view into the modern cabin, surrounded by greenery. A refreshing drink rests on a side table, complementing the serene outdoor setting.

Cabin in Exeter

5 out of 5 average rating, 114 reviews

Tiny Cabin Exeter Outdoor Bath and Horse Property

@littleburrow_cabinandcottage Enjoy a relaxing couples retreat at this stylish tiny house. Set on 6 peaceful acres of a boutique equestrian property near the charming village of Exeter. Surrounded by small farms experience the peace of the countryside while still being only a short drive to the popular towns and destinations of the Southern Highlands. This tranquil area is especially quiet at night when guests can enjoy the deck, firepit and outdoor bath while gazing at the stars above

Top guest favorite

A charming cottage is framed by lush greenery, featuring a distinctive round window and a warm wooden exterior. A welcoming outdoor seating area is set around a firepit, where smoke gently rises. Soft light reflects off the exterior, enhancing the tranquil atmosphere.

Cottage in Sutton Forest

4.98 out of 5 average rating, 111 reviews

Fantoosh

Welcome to your blissful getaway! This beautifully designed picture-perfect cottage is nestled in the heart of Sutton Forest, the ideal fit for anyone looking to relax and unwind. Enjoy the heated floors and an Internal fire at the press of a button. Firepit outside awaits, sizzle a steak or toast marshmallows under the stars. Snuggle up on the couch, stream a movie you never got to see or work on the super fast internet. Take a walk along the country lanes and enjoy the fresh air.

Guest favorite

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

4.92 out of 5 average rating, 364 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 favorite

The exterior of a charming residence is visible, framed by manicured gardens. A symmetrical layout showcases two vibrant trees with red foliage, while the building features light-colored walls, a metal roof, and inviting entry doors. Surrounding greenery adds to the serene atmosphere.

Guest suite in Bowral

4.94 out of 5 average rating, 144 reviews

Arcadia at Hopewood House

Situated near to the original Hopewood Residence, lies ‘Arcadia’. Self-contained with private entry from the garden - ‘Arcadia’ - perfect for a couples escape. Set on the beautiful, private estate of one of Australia's most renowned landscape artists, this is truly a unique opportunity to explore the grounds of curated sculptures, artwork and rare botanicals. If you would like to visit the private Hopewood Gallery of Tim Storrier while you are staying please contact Janet .

Top guest favorite

A charming cottage is nestled among mature trees and lush greenery. A welcoming porch is visible, framed by garden beds and wooden fencing. The sloped roof and white exterior contribute to a peaceful, inviting ambiance in this tranquil garden setting.

Cottage in Berrima

4.98 out of 5 average rating, 399 reviews

Ardleigh Cottage in Berrima Village

Situated in the heart of historic Berrima, Ardleigh Cottage offers the discerning traveller all of the comforts of home in a tranquil and relaxing garden setting. Quiet yet very close to the many attractions of Berrima, this private abode is the perfect place for your Highlands stay. A historic pub, a cellar door, galleries, speciality shops, cafes, restaurants, historical places of interest and beautiful bush walks are all within walking distance from the cottage.

Top guest favorite

A weathered wooden dock extends over still water, bordered by lush greenery and distant trees. Reflections on the water create a serene atmosphere, while a steel railing leads towards the edge, inviting moments of contemplation surrounded by nature.

Cottage in Mittagong

5 out of 5 average rating, 275 reviews

Sedalia Farm Cottage - stunning rural retreat

Enjoy the serenity and truly picturesque backdrop of captivating rural vistas at this unique charming, private stand alone cottage that sits separately from the main farm house. It is only a short ten minute drive to Bowral or Mittagong. Wake up to the sounds of nature and enjoy the lush gardens that provides a quiet sanctuary in an incredibly tranquil location. Sedalia Farm has 3 Alpacas, 1 horse, 1 miniature donkey and 2 Huskies who all live on the property!

Top guest favorite

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, 167 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.

Guest favorite

A tranquil landscape featuring a mix of native Australian trees and shrubs. The scene captures a clear sky and soft morning light, highlighting the varied greens of the vegetation. In the background, gentle hills are visible, creating a sense of serene wilderness.

Apartment in Berrima

4.96 out of 5 average rating, 533 reviews

Magpie Haven Berrima

Magpie Haven is a north facing independent studio with king size bed, in a separate pod of our architect designed, contemporary home. We are on 1.5 acres overlooking the Wingecarribee River, the village of Berrima and beyond. It is 1 km into Berrima where you will find cafes, restaurants and specialty shops and close to Bendooley Estate and other wedding venues.