Holiday rentals in Winterton

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Top-rated holiday rentals in Winterton

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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
4.97 out of 5 average rating, 135 reviews

Grassroots Guesthouse - DRAKENSBERG ECO ESTATE

PRIVATE ECO ESTATE: CENTRAL DRAKENSBERG Recently purchased and fully renovated - Grassroots is ready to welcome you! We have designed the house with our guests' happiness at heart. The house is in the exclusive private eco estate - Cathkin Estate, 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 spacious living area is framed by large sliding glass doors, offering a clear view of the surrounding mountains and valleys. A dining table set for guests is positioned near the window, inviting natural light into the room. Cozy seating adds to the inviting atmosphere.
Guest house in Cathkin Park
4.93 out of 5 average rating, 28 reviews

Highbourne Cottages - Aloe

An eco-friendly, off grid self-catering family style cottages part of the Monks Cowl Drakensberg World Heritage Site in KZN, South Africa. This is the perfect home away from home for anyone looking to relax. Whether it is hiking in the mountains, surrounded by beautiful nature, wildlife and birds, relaxing next to our natural stream that runs through the property with a book or wondering around the shops and restaurants down the road - there is something for everyone here at Highbourne Cottages.

Top guest favourite
The cottage is shown from an elevated angle, with a covered patio extending from the structure. Lush green fields and rolling hills are visible in the background, alongside a peaceful stretch of the Mooi River. Clear skies add to the serene landscape.
Cottage in Nottingham Road
4.99 out of 5 average rating, 117 reviews

Coldstream Cottage

Set on a 20hectare property on the banks of the Mooi River, Coldstream Cottage is the perfect place to unwind. Enjoy the beautiful views on the verandah, stroll down to the river or have an early morning run. The cottage is an architect designed, open plan, one bedroom unit with partly open plan bathroom. Morning sun pours through expansive glass panes, a free standing fireplace and solid wood floors help keep it warm in winter. A 20 minute drive gets you to Nottingham Road shops and restaurant

Guest favourite
A thatched cottage is set amid lush green lawns, showcasing large windows that allow natural light to fill the space. A patio area features light-colored seating, and the cottage is surrounded by trees, adding to the peaceful atmosphere.
Farm stay in Bergville
4.82 out of 5 average rating, 125 reviews

Saligna Dam View Guest House

Beautiful thatched cottage with an extra Rondavel set on our farm in the Northern Drakensberg area. It has its own private garden with lawns down to the edge of the dam. In the corner is a gorgeous private swimming pool to enjoy sundownders in on hot lazy summer evenings or keep the kiddies busy. The pool is safely fenced off. Ideal for a couple or a larger group. Lovely farm holiday for all. Although it can sleep 10 comfortably it is perfect for a cosy get away for just two. You will love it.

Guest favourite
A unique, owner-built unit with a rock-inspired design is set against a backdrop of majestic mountains. Lush green lawns and diverse plants frame the property, creating a natural ambiance. The serene landscape features rolling hills, inviting a peaceful retreat in a private environment.
Place to stay in Winterton
4.93 out of 5 average rating, 176 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.

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
4.92 out of 5 average rating, 116 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.

Guest favourite
The farmhouse is viewed from the garden, surrounded by lush greenery and large trees. A tranquil outdoor pool reflects the sky, with a wooden deck providing access. Cozy seating areas are visible, enhancing the spacious, serene atmosphere of the property.
Villa in Winterton
4.85 out of 5 average rating, 54 reviews

Glenside, an historic Drakensberg farmhouse

This gracious farmhouse situated on a working farm is over 100 years old. It is an ideal getaway for large families and friends. Explore the farmlands , veld and river on foot, cycle the tracks, discover the wildlife or simply enjoy the sweeping views of the Central Drakensberg from the wraparound verandah . The fireplaces in the lounge and dining room are ideal for cosy winter evenings indoors and the large fenced garden has both sunny and shady spots for daytime relaxing.

Guest favourite
The cottage is surrounded by lush greenery, with a modern exterior featuring a corrugated metal roof. A private patio is visible, furnished with wooden chairs and a table, ideal for outdoor relaxation. Large windows allow natural light to fill the space.
Guest suite in Cathkin Park
4.75 out of 5 average rating, 106 reviews

Cathkin Peak Cottage

A blissful, comfortable cottage nestled in the heart of the Central Drakensberg. This cozy accommodation boasts breathtaking views of Cathkin Peak and Champagne, as well as the surrounding mountain range. It's located near all the major hiking routes, making exploration an easy step out the door. The cottage itself is equipped with a fully functioning kitchenette, bathroom, lounge, private patio, bedroom, and entertainment room. Perfect for a single, couple, or small family.

Top guest favourite
A modern vehicle is parked on a green lawn in front of a white building with a distinctive roofline. Surrounding hills are visible in the background, while a large tree provides shade. The entrance features wooden accents and windows, offering a glimpse of the scenic landscape.
Barn in Van Reenen
4.9 out of 5 average rating, 382 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 can be booked in advance. Safe and convenient for single female travelers with manager living next door. No charge for children/elderly parent sleeping on lounge bed if accompanied by both parents.

Guest favourite
The cottage exterior is framed by lush greenery and vibrant flowers. A sloped roof accentuates the structure, while large windows invite natural light. The surrounding lawn is well-maintained, offering a serene environment with tall trees in the backdrop, contributing to a peaceful retreat.
Cottage in Winterton
4.95 out of 5 average rating, 101 reviews

The Goodland Milk Cottage - Farm Style Cottage

Milk Cottage is completely private and secluded.You’ll love the tranquility, large open spaces and fresh air. The beds are made up with fresh white linen, fluffy white towels are provided. The cottage is good for couples, friends or families as it has two en-suite bedrooms with a queen size bed in each. TV with Netflix, selected Dstv and free WiFi. Full kitchen and braai and a cozy fireplace in the lounge. Gas stove and inverter-battery back-up during loadshedding.

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, 90 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, 175 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 10 holiday rentals in Winterton

  • Nightly prices starting at

    Winterton holiday rentals start at € 34 per night before taxes and fees

  • Verified guest reviews

    Over 40 verified reviews to help you choose

  • Wifi availability

    10 of Winterton holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Winterton rentals