Holiday houses in Winterton

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Top-rated holiday rentals in Winterton

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Top Guest favourite
The outdoor area of the guest cottage features a private garden with well-maintained grass and a wooden fence that ensures privacy. A small patio with seating is visible, while the backdrop includes rolling hills and a cloudy sky that highlight the natural beauty of the surroundings.
Cottage in KwaZulu-Natal
4.99 out of 5 average rating, 77 reviews

Drakensberg Bungalow

John and Debby welcome you to a peaceful, tastefully decorated, self contained guest cottage within Bergview Private Estate in the Central Drakensberg, a World heritage site. Queen bed, full dstv, ceiling fans, kitchen, lounge, en suite bathroom with shower await, as you step into this little piece of Heaven on earth. Beautiful views, hikes, outdoor activities right on your doorstep. Restaurants, supermarket, a canopy tour, reptile and raptor centres nearby. A nature reserve a short drive away.

Top Guest favourite
A charming farmhouse is framed by lush greenery and colorful flower beds. White flowers bloom prominently in the foreground, contrasting with the soft green of the surrounding plants. The building features a sloped roof and large windows, inviting natural light into the interior.
Farm stay in Nottingham Road
4.93 out of 5 average rating, 167 reviews

Yellowwoods Farm - WILLOUGHBYS COTTAGE

We like to think that we have the best of both worlds here at Yellowwoods! The benefits of farm life, yet easy access to cafes, restaurants, bicycles trails, farmers markets, golf courses and schools. Only 2kms off the N3, we are easily accessible and very easy to find. We are a little farm so expect a bit of ‘farm noise’ about and general day-to-day goings on. Willoughbys has both inside and outside table/chairs & braai facilities - Weber as well as outside braai+'firepit'. WiFi and DSTV.

Guest favourite
The exterior of a uniquely designed stone unit is framed by lush greenery and vibrant orange flowers. The backdrop features dramatic mountains with snow-capped peaks under a partly cloudy sky, highlighting a tranquil outdoor setting.
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
The outdoor area features a circular swimming pool framed by landscaped gardens and rolling green hills in the background. Lush foliage and colorful flowers adorn the space, providing a natural and serene atmosphere. Clear skies create a bright and inviting setting.
Home in Van Reenen
4.84 out of 5 average rating, 192 reviews

Llandaff Summer House

Llandaff House Van Reenen is 4 bedroom California style house built in 1950's. Perched on the edge of the escarpment with a fabulous view. Laze for days in front of the massive fireplace, or venture out and explore one of the 3 gorges. Start your holiday here on route to the coast or meet friends mid-way from JHB & Durban for a getaway or celebration, or a wedding at the little church just up the road. We also have 3 cottages, Woodlands and The Barn and The Old Barn.

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, 115 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
The exterior of the house is surrounded by lush greenery, with a stone-paved driveway leading to the entrance. Majestic mountains are visible in the background under a clear blue sky, creating a serene natural setting.
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 private patio area is framed by natural greenery, featuring seating for two and a charcoal grill. The entrance to the cottage showcases large glass doors that invite light indoors. The simple architecture complements the surrounding landscape of Central Drakensberg.
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.

Top Guest favourite
A panoramic view of Bell Park Dam is presented, surrounded by sweeping green hills and fields. The water reflects the sky, creating a serene landscape. The distant Drakensberg mountains rise majestically, contributing to the tranquil atmosphere.
Cottage in Cathkin Park
4.96 out of 5 average rating, 73 reviews

Shepherd Farm - mountain tranquility.

Situated in the Central Drakensberg, Shepherd Farm is perched on a ridge overlooking the Bell Park Dam, and the majestic Champagne and Cathkin peaks of the Drakensberg mountains. These mountains form part of the Maloti Drakensberg Transboundary World heritage Site, renowned for its spectacular natural landscapes and beautiful fauna and flora. Our cottage is light and modern, comfortable and welcoming, with a modern kitchen, 2 full bathrooms, Netlix and WiFi.

Guest favourite
Farm stay in Winterton
4.91 out of 5 average rating, 76 reviews

The Willow Cottage @ Tranquility Farm Stays

The Willow Cottage is located on the beautiful Tranquility farm in the Central Drakensberg. This newly renovated cottage is perfect for a small family or couple accommodating up to 3 guests (2 adults & 1 child). On your stay, enjoy views of the mountains, an onsite reservoir converted swimming pool with an expansive deck for sunbathing/ sundowners, jungle jim, farm walks, 2 dams (catch & release welcome) and the rest & relaxation the farm offers.

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..

Top Guest favourite
An inviting outdoor area includes a clear swimming pool edged by a stone patio. In the background, expansive fields stretch towards distant mountains under a soft sunset glow, with a serene water body visible nearby.
Farm stay in Winterton
4.89 out of 5 average rating, 181 reviews

Noodhulp Holiday House

Our house is close to the Central Drakensberg and 5km outside of Winterton. You’ll love panoramic view of the Drakensberg. A fireplace and an entertainment area with a pool and table tennis table. Patio with braai facilities. A pool and deck. There is walk to the dam or river on the property. 3 garages. Our house is good for couples, business travelers, families (with kids), and big groups.

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 $51 NZD 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