Holiday rentals in Winterton

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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 $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 50 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

  • 4.5 Average rating

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

Top-rated holiday rentals in Winterton

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

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Guest favourite
The exterior of the cottage features a sloped roof and a welcoming entry door. A wooden deck is visible, equipped with a table and chairs, ideal for outdoor dining. The vibrant garden blooms with flowers, enhancing the serene environment.
Home in Cathkin Park
4.89 out of 5 average rating, 37 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.

Guest favourite
A newly built modern cottage is showcased, featuring a large glass front and gabled roof. The surroundings include expansive fields and mountains in the distance under a clear blue sky. Nearby, a tree offers shade on the lush grass.
Cabin in uThukela District Municipality
4.91 out of 5 average rating, 47 reviews

Northington, Mountain escape

Explore the freedom of 900 hectares of untouched wilderness on a private nature conservancy in the heart of the Kamberg. Start your day with coffee on the mountain as black wildebeest roam below, or spend a quiet morning fly-fishing at your own private trout dam. Explore scenic hiking trails, spot rare bird species. After your adventures, relax in the comfort of a newly built modern cottage — fully equipped with all the amenities you need for a luxurious countryside escape. 4x4 cars needed!

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, 189 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 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
4.94 out of 5 average rating, 120 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, 162 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
The cottage exterior showcases a spacious covered verandah, surrounded by lush greenery. Comfortable outdoor seating is arranged with a family-style dining table, providing ample space for gatherings. Large sliding doors offer visibility into the interior, where natural light enhances the welcoming atmosphere.
Home in uMgungundlovu District Municipality
4.96 out of 5 average rating, 109 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.

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, 74 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.

Top guest favourite
A private patio is shown, featuring a wooden jacuzzi with lush gardens visible in the background. A round table is set with tea and refreshments, while stunning mountain views encompass the scene, enhanced by a shaded area above.
Home in Cathkin Park
5 out of 5 average rating, 39 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
4.93 out of 5 average rating, 120 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
Barn in Van Reenen
4.9 out of 5 average rating, 429 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.

Guest favourite
Guest suite in Winterton
4.83 out of 5 average rating, 63 reviews

Nyati Valley Berg House, Champagne Castle

Mountain views, Amazing views of Cathkin Peak and Champagne Castle, Solitude, Peace, Open Spaces, Countryside Atmosphere, Free parking, great for pets, relaxing, many nearby amenities. Berg House 29° 2'13.87"S 29°26'0.74"E Sleeps 6 Adults and child cot or bed can fit comfortably. There are 3 Ensuite Bedrooms There is also a 2-sleeper cottage available on the property as a separate booking.

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
4.88 out of 5 average rating, 182 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