Holiday houses in Winterton

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Top-rated holiday rentals in Winterton

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Guest favourite
A spacious wooden deck extends from the cottage, featuring outdoor seating and a patio umbrella. The two-story structure boasts a modern roof and large windows, showcasing a serene view of the surrounding landscape and mountains.
Home in Cathkin Park
4.89 out of 5 average rating, 36 reviews

Highbourne Cottages - Protea | Mountain Retreat

Tucked away on the side of a mountain overlooking the surrounding mountains. Protea cottage is open plan family cottage with the heart of the cottage opening onto a wooden deck – the perfect spot to watch the setting sun. The cottage sleeps up to four people with one large open planned studio-style bedroom on the ground floor and an open loft upstairs with two single beds, just perfect for a family of 4. The studio design allows flow from the well-equipped kitchen to the lounge area and bedroom.

Top Guest favourite
A covered porch features two reclining chairs arranged on polished wooden flooring, offering a serene view of rolling hills and a tranquil dam. Lush greenery and trees frame the landscape, creating a sense of peaceful seclusion.
Cottage in Dargle
4.95 out of 5 average rating, 327 reviews

Beautiful Breeze Cottage

Beautiful Breeze Cottage sits among the stunning hills of the Dargle Valley. It overlooks 3 tranquil dams, rolling pastures and an indigenous forest. There are cattle and horses in the fields, abundant bird life to enjoy and peacefulness to breath in. It's the perfect place to recharge while escaping the pressures of city life and with the Midlands Meander on our doorstep you can be as busy or as quiet as you choose. The farm is now fully off Eskom power so load shedding is a distant memory.

Guest favourite
Place to stay in Winterton
4.94 out of 5 average rating, 186 reviews

Inkunzi Cave - A Unique African experience.

Situated in one of the safest, crime-free areas of SA, with tar roads all the way, is INKUNZI CAVE. A totally unique, owner built unit with a Bushman theme. 1 bedroom only with double bed. Single bed in lounge . An amazing "rock" bath and separate shower. Overlooks a beautiful rock pool. Very private. 2 other cheaper units on the property are listed separately: THE ZULU HUT, and DIDDLY SQUAT. All have stunning mountain views, are comfortable and fully equipped for self catering.

Top Guest favourite
A cascading waterfall flows over a rocky ledge, surrounded by lush greenery and rolling hills. The frothy water creates a serene atmosphere, while a small group of individuals can be seen enjoying the view from a safe distance on the rocky outcrop.
Farm stay in Van Reenen
4.93 out of 5 average rating, 132 reviews

Waterfall River Lodge

This is a unique, comfortable, fully kitted, self-catering house sleeping 8/10 people. Hidden in a quiet corner of our working farm it overlooks a pristine section of the Wilge River, with the famous waterfall and Nelson's Kop mountain providing spectacular scenery. Guests will be able to enjoy absolute peace, uninterrupted views and walks in almost every direction. Please note that the property is remote and the last 200m of the access road will require a high clearance vehicle.

Top Guest favourite
A tranquil view of a farmhouse nestled among trees, set beside a large pond with ducks swimming. The scene captures the serene natural landscape, framed by autumn foliage and the gentle reflection of the house on the water's surface.
Farm stay in Balgowan
4.97 out of 5 average rating, 112 reviews

Peaceful Farm Retreat - Summerfield Farmhouse.

Enjoy peaceful but sophisticated living on a tranquil working farm with cattle, sheep, chickens and ducks. Walk in the indigenous forests, run, ride bikes, paddle our kayaks on the dam or just sit next to your fireplace and relax. Entire four en-suite bedroom home with ample living and entertaining spaces for exclusive use. A lovely family stay venue. Price is for 4 people. Additional guests charged extra. Maximum 8 guests allowed. NB Large duck pond 20 M from the Farmhouse.

Guest favourite
A modern cottage is set amidst lush greenery, featuring large glass doors that allow natural light to fill the interior. An outdoor seating area is shaded by a large umbrella, while a chimney adds to the cozy exterior. Scenic views are visible beyond the cottage.
Cottage in Cathkin Park
4.95 out of 5 average rating, 116 reviews

The Goodland - Cottage One

Perfect for a relaxing couple’s mountain getaway or work remotely. The garden boasts 200 year old trees and abundant bird life. Enjoy panoramic mountain views from the veranda. The cottage boasts an uber comfy king size bed, fluffy towels included. En-suite bathroom with walk-in shower. Well equipped kitchen with Nespresso machine. Fast WIFI. Netflix. Cozy fireplace for cold days. Fire pit. All self-catering. Explore nearby shops and restaurants or hike in the berg.

Top Guest favourite
A rock pool, surrounded by lush vegetation, offers a serene swimming spot with clear water reflecting the sky. Fencing ensures safety, while expansive views of rolling hills and distant mountains create a tranquil natural backdrop.
Villa in Cathkin Park
4.96 out of 5 average rating, 160 reviews

Grassroots Guesthouse - DRAKENSBERG ECO ESTATE

PRIVATE ECO ESTATE: CENTRAL DRAKENSBERG Grassroots is ready to welcome you! We have carefully designed the house with our guests' happiness at heart. The house is in the exclusive private eco estate - Cathkin Estates, bordering the uKhahlamba Drakensberg Park World Heritage Site. The estate exceeds 1,000 hectares, with an abundance of free roaming wildlife (zebra, eland, wildebeest, oribi etc) and a host of birds and flora. A dreamy location for any nature lover!

Guest favourite
A panoramic view of the cottage nestled among trees and greenery, framed by the expansive Central Drakensberg mountain range. Lush hills and valleys extend towards the horizon, under a clear blue sky with a few scattered clouds.
Guest suite in Cathkin Park
4.76 out of 5 average rating, 157 reviews

Cathkin Valley View Cottage

This scenic, homestyle cottage cradles the famous mountain range of Central Drakensberg. The private accommodation features a spacious patio overlooking the breathtaking mountains and sweeping valley. Guests can enjoy a braai, fire pit, and outdoor shower in the lush garden. The cottage includes a bathroom, fully functioning kitchen, an entertainment and lounge area equipped with Apple TV, and a cosy bedroom. This cottage is ideal for couples, and pets are welcome.

Guest favourite
An inviting living area features a comfortable seating arrangement with a light-colored couch and a wooden coffee table. A wood-burning fireplace is visible along with a TV mounted on a brick wall. Large sliding doors open to a patio, enhancing the connection with the outdoors.
Home in uMgungundlovu District Municipality
4.97 out of 5 average rating, 107 reviews

NGUNI RIDGE - Farm Cottage in the KZN Midlands

This charming farm cottage is perfectly located on Sakabula Country Estate. Just a short drive from Howick, you’ll have easy access to quaint cafés, farm stalls, and the famous Midlands Meander, offering everything from artisanal goods to outdoor adventures. Wake up to beautiful farm views and enjoy the Nguni cows grazing. Whether you're looking for a romantic retreat, a family getaway, or a weekend with friends, this cottage is a warm, welcoming and relaxing.

Guest favourite
Home in Cathkin Park
5 out of 5 average rating, 37 reviews

Ama Casa - Kingfisher - Jacuzzi with Mountain View

The cottage is nestled within beautiful indigenous gardens. For that special occasion, honeymoon or escape from the stress of everyday life in the city, Kingfisher is the ideal romantic getaway for a couple. Whether you relax in your own jacuzzi on the private patio & garden space with magnificent views of the Central Drakensberg Mountains or participate in the many activities in the valley, the cottage offers a secluded haven for you to relax and unwind!

Top Guest favourite
A welcoming entrance features a spacious porch covered by a wooden overhang. Potted plants and barrels are placed along the path, complementing the natural setting. A sturdy wooden door is centered at the front, with large windows allowing for natural light.
Cabin in Winterton
4.92 out of 5 average rating, 118 reviews

Garden Cottage

Nestled in the town of Winterton just below the Central Drakensberg is this lovely solar powered self catering cottage. King size bed (can be split into two 3/4 beds), WIFI, kitchen and undercover parking. Bathroom has a shower. A short drive away from a variety of sites, hikes and activities in the Berg. Coffee shops and restaurants within a few minutes drive. Please note: there is a private pool, for hosts only, that isn't fenced off..

Guest favourite
A serene landscape is depicted, showcasing lush green fields dotted with white flowers. Two trees stand prominently, providing shade and a sense of tranquility. The distant hills create a gentle backdrop, highlighting the natural beauty of the surrounding environment.
Barn in Van Reenen
4.9 out of 5 average rating, 424 reviews

A barn with great views of the valley into KZN

A hop, skip and a jump off the N3, situated in in the Van Reenen Eco Village Precinct. Down the road from the little church tea garden. A great one night stop off. Breakfast at the Tea Garden (not included) or take a early morning walk before continuing with your journey. Dinner pre-ordered for delivery. Good parking for Caravans and trailers. No charge for children/elderly parent sleeping on lounge bed if accompanied by both parents.

Popular amenities for Winterton holiday rentals

Quick stats about holiday rentals in Winterton

  • Total holiday rentals

    Explore 20 holiday rentals in Winterton

  • Nightly prices starting at

    Winterton holiday rentals start at $43 AUD per night before taxes and fees

  • Verified guest reviews

    Over 50 verified reviews to help you choose

  • Wi-Fi availability

    10 of Winterton holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winterton rentals

  • 4.5 Average rating

    Winterton stays receive an average rating of 4.5 out of 5 from guests