Holiday rentals in Penrose

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Penrose

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
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, 118 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
Cabin in Exeter
5 out of 5 average rating, 133 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

Guest favourite
A cozy seating area features large windows that provide a view of the surrounding bushland. A comfortable black bench seat is adorned with soft pillows and a textured blanket. Natural light fills the space, highlighting the wooden accents and creating a serene atmosphere.
Tiny home in Tallong
4.93 out of 5 average rating, 333 reviews

Wildernest "T1" - Off-Grid Wilderness Experience

Looking for an adventure, an escape, or just an opportunity to reconnect with nature? ‘Wildernest’ offers a unique off-grid experience, staying in a tiny house (nicknamed "T1") nestled amongst the bushland on the edge of the Wingello Forest. A perfect sanctuary to relax and rejuvenate. Or as a base for an adventure - bush walking, mountain biking, wildlife spotting - or perhaps exploring the Southern Highlands foodie hot spots is more your thing. Come with friends and book Wildernest "T2" too!

Guest favourite
A gravel driveway leads to a charming cottage nestled among trees. The building is partially obscured by morning mist, showcasing its muted colors and distinctive X-framed doors. Lush greenery lines the pathway, providing a serene entry to the home.
Cottage in Bundanoon
4.95 out of 5 average rating, 361 reviews

Pear Tree Cottage

Enjoy a peaceful country retreat in the heart of the Highlands surrounded by nature at its best. This spacious, newly renovated, two-bedroom cottage is a separate dwelling situated on 5 acres of parkland that can sleep up to 5 people. It has a kitchenette (please note: no oven, but have a small stove), comfy lounge with a cosy warm fireplace for cold nights and is just a 5 minute drive to Bundanoon village. Pear Tree Cottage gets its name from the ornamental pear trees that line the driveway.

Top guest favourite
Farm stay in Moss Vale
5 out of 5 average rating, 213 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
Cabin in Sutton Forest
4.95 out of 5 average rating, 143 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 verdant landscape is visible, featuring lush green fields and scattered trees under a clear blue sky. A small shed is positioned on the property, surrounded by flowering bushes and a wooden fence that encircles the paddocks.
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 wooden hot tub is nestled among tall trees, surrounded by lush ferns and greenery. The calming water reflects the natural setting, inviting relaxation in a serene outdoor environment.
Guest suite in Penrose
4.98 out of 5 average rating, 658 reviews

The Studio @ The Vale Penrose

The Vale is a masterpiece of rural design, encompassing expansive manicured grounds, an eclectic mix of farm animals and wildlife and a range of luxurious accommodations to suit the most discerning taste. The Studio @ The Vale is the perfect location for that special weekend away or that midweek escape from the hustle and bustle of the daily grind. A private Spa nestled among the rainforest perfectly complements the already decadent offering.

Top guest favourite
Cottage in Exeter
4.98 out of 5 average rating, 176 reviews

The Shack at Bimbimbi in semi rural Exeter.

The Shack at Bimbimbi is well appointed, private, and is situated on 5 acres, 40 meters from the main house separated by gardens. There is a box fire and heating for chilly nights. A great getaway, close to walks in Morton National Park, Bundanoon, Exeter Village and a short drive to Moss Vale and Bowral. A complimentary breakfast hamper is supplied for a minimum 2 night stay, free WiFi. We hope you will come and see for yourself.

Guest favourite
The exterior of a timber yurt is displayed, featuring an octagonal structure with a gently sloped roof. The entrance is framed by a wooden door, with large windows showcasing the lush greenery surrounding the property. A peaceful garden complements the inviting atmosphere.
Yurt in Bundanoon
4.81 out of 5 average rating, 340 reviews

Eureka Yurts! A unique Highlands experience

Looking for something different? Escape to our self-contained yurt (octagonal timber cottage). Featuring super-comfy double bed with electric blanket, large en-suite bathroom, separate kitchen and spacious private deck. Sparkling wine and chocolates make your arrival extra special, delicious continental breakfast provided , plus air-conditioning, TV and WIFI. A perfect base from which to explore the beautiful Southern Highlands.

Guest favourite
A modern cottage is viewed from a gravel driveway, featuring wooden siding and large windows. An outdoor seating area is visible beside the entrance, with the landscape unfolding into distant hills under a clear blue sky.
Tiny home in Bundanoon
4.9 out of 5 average rating, 139 reviews

The Lazy Duck, Bundanoon

The Lazy Duck is just 300m walk from the center of town yet has a feeling of being on top of the world. Stunning views over the Morton National Park from one of the highest points in town. Looking into Kangaroo Valley. It is right next door to Osborn House, on its own private fenced block. The cottage is nestled in the trees with a huge picture window. You won’t forget your time in this romantic and memorable place.

Guest favourite
An open cabin interior features a cozy sleeping loft above, with a spacious bed clad in warm tones. Below, a sunken lounge area includes a comfortable sofa adorned with textured throws. Large windows frame views of the surrounding bushland, allowing natural light to fill the space.
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.

Popular amenities for Penrose holiday rentals