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Holiday houses in Penrose

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Top-rated holiday rentals in Penrose

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Top Guest favourite
An aerial view showcases a modern retreat featuring a striking combination of dark and warm exterior tones. The outdoor area includes a seating space near a firepit, with landscaping enhancing the natural surroundings. A deck extends from the side, integrating outdoor living with the serene setting.
Tiny home in Penrose
4.99 out of 5 average rating, 121 reviews

The Hideaway at Sylvan Glen Estate

Unique and stylish, The Hideaway is located within Sylvan Glen Estate, privately situated between The Homestead and The Cottage. It's a couple's only retreat, with luxurious finishes including full kitchen, 72sq/m living area, deck, firepit and even a wood fired outdoor bathtub. Airconditioning, king bed with Egyptian linens, 16 sq/m ensuite with double shower, sun deck overlooking the Estate's 7th fairway. It's a special place for special memories - quiet countryside with city inclusions -enjoy

Top Guest favourite
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, 136 reviews

Tiny Cabin Exeter Outdoor Bath and Horse Property

@littleburrow_cabinandcottage A relaxing couples retreat at this stylish tiny house on 6 peaceful acres of our boutique equestrian property 2km from the charming rural village of Exeter with its popular cafe. Surrounded by small farms and the peace of the countryside while still being only a drive-(Bundanoon 10mins Mossvale 15min drive) to the charming towns of the Southern Highlands. Its especially quiet at night-enjoy the firepit & outdoor bath while gazing at the stars. Small dogs on request

Top Guest favourite
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, 606 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 favourite
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, 214 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.

Guest favourite
Two individuals sit in chairs around an outdoor fire pit, with flickering flames providing warmth and light. A small table holds flowers, surrounded by a backdrop of dense trees and foliage, creating an intimate atmosphere in the evening setting.
Cabin in Sutton Forest
4.95 out of 5 average rating, 145 reviews

Unique'Danglestone' Couples Hideaway in the Forest

Awe inspiring views surrounded by nature. Nestled in the lush greenery of a private forest this modern architecturally designed cabin is luxury at its best. With the warmth of the heated floor & indoor gas fire you will be toasty warm all year round. Sutton Forest is very near several vineyards and villages. An ideal location to escape the city. PETS allowed but please disclose when booking- Max 2 people only (not suitable for infants) 1 Queen bed only MASSAGE available nearby (plse ask)

Top Guest favourite
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
4.99 out of 5 average rating, 138 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.

Top Guest favourite
The cottage features a modern design with a welcoming entrance. A stone chimney complements the black exterior, while a covered porch invites relaxation. Lush greenery surrounds the property, which overlooks open fields with grazing animals in the distance, framed by tall trees.
Cottage in Bundanoon
4.97 out of 5 average rating, 302 reviews

Contemporary Country Experience

Contemporary country experience Enjoy the simplicity and restoration that rural peace offers without getting your hands dirty (*unless you want to!). This design inspired cottage provides a place for up to 6 people to take in the sunset sitting by the open fire, then wake to collect fresh eggs and watch the horses, cows and kangaroos graze, or wander down to the creek for a picnic. The cottage is fully enclosed in a fenced area 800m2. We have changed the fencing so none is electric.

Top Guest favourite
A horse wearing a gray blanket stands near a wooden fence, surrounded by lush greenery and paddocks. Tall trees provide shade, and a clear blue sky with scattered clouds enhances the rural landscape. The paddocks extend into the background, dotted with additional trees.
Barn in Penrose
4.96 out of 5 average rating, 141 reviews

The Shed at Penrose

Cosy self Contained Apartment on a small 5 acre working horse training property based in Penrose, Southern Highlands NSW Our apartment can accomodate a couple or a family of 4 making it an easy choice for somewhere to stay whilst visiting the beautiful Southern Highlands. Be greeted in the morning by our small family of horses or bring your own horses for a riding holiday, where an accredited coach is also available for lessons and the Penrose forest is on our doorstep.

Top Guest favourite
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, 314 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!

Guest favourite
The cabin is positioned on a grassy area, surrounded by tall trees. Large bi-fold doors open to a private deck, with steps leading to an inviting entrance. The exterior features a mix of natural and metal textures, creating a blend of rustic and modern elements.
Tiny home in Exeter
4.86 out of 5 average rating, 195 reviews

Southern Highlands Vineyard Cabin by Outpost

Welcome to our premium country cabin nestled within the picturesque wineries of the Southern Highlands! Set amongst the vines of Exeter Vineyard & Cellar Door, our cosy, private retreat offers a unique experience where you can unwind, sip local wines, and bask in the breath-taking beauty of the Australian countryside. Please Note: We offer a discounted nightly rate for mid-week bookings (Sun-Thurs).

Guest favourite
A custom-built cabin is partially visible among tall Australian Scribbly Gums. A wooden deck features a chair, inviting relaxation in a serene outdoor setting. A fire pit surrounded by logs is located nearby, adding to the rustic ambiance.
Farm stay in Penrose
4.88 out of 5 average rating, 126 reviews

ARUNA Estate off-grid cabins

ARUNA Cabins provide the ultimate off-grid experience. Nestled amongst the Australian Scribbly Gums, it offers a bush view, down to the River. If you want to get as far as possible from the bustling world, the ARUNA cabin is for you. Custom built for their bush location, our cabins provide a stylish and snug escape. They are completely off grid so you can ensure your total freedom from the everyday.

Guest favourite
A spacious interior features high cathedral ceilings with wooden beams and warm lighting. Comfortable seating areas are arranged, accompanied by a colorful area rug. Large windows invite natural light and provide views of the surrounding bushland, while artwork and decorative touches enhance the unique atmosphere.
Earthen home in Bundanoon
4.96 out of 5 average rating, 312 reviews

The Artist's House, Bundanoon NSW

Discretely situated amongst bushland yet just a short stroll from the village of Bundanoon, is The Artist's House. Handcrafted by a well known local artist, this enchanting property offers you a very special and unique getaway for one or two couples. See guest access information for pricing information if you require more than one bedroom.

Popular amenities for Penrose holiday rentals