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, 154 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!

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, 127 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

Superhost
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
4.83 out of 5 average rating, 138 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.

Top 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
4.94 out of 5 average rating, 32 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
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, 183 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 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, 108 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
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
4.83 out of 5 average rating, 178 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, 110 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 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, 67 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 hot tub is positioned on a private patio, offering views of expansive green gardens and the Central Drakensberg Mountains in the background. The calming scene is complemented by touches of native foliage and a clear sky, enhancing the sense of tranquility.
Cottage in Cathkin Park
4.97 out of 5 average rating, 30 reviews

Ama Casa - Hoopoe - Jacuzzi with Mountain Views

The cottage is nestled within beautiful indigenous gardens. For that special occasion, honeymoon or escape from the stress of everyday life in the city, Hoopoe 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!

Guest favourite
A modern structure features large glass doors, allowing natural light to fill the space. Curtains softly drape at the windows, and the overhanging roof provides shade. The exterior walls display a muted color, complemented by landscaped greenery in the foreground.
Guest suite in Nottingham Road
4.77 out of 5 average rating, 106 reviews

Our Place @ Notties: Self-contained 1-Bed Unit

Take it easy at this unique and tranquil getaway. In close proximity to most Nottingham Road tourist sites. Walking distance to Clifton Preparatory School 2 km from Gowrie Golf course. 10 km from Michaelhouse. Ideal stay for those attending Weddings and/or visiting Spas in KZN Midlands 6 km from Fordoun 6 km from Netherwood Farm & Blueberry Cafe 8 km from Brahmanhills 10 km from The Gallery NO LOADSHEDDING: Solar and backup Generator on site.

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, 109 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..

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 £22 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