Vacation rentals in Winterton

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Top-rated vacation rentals in Winterton

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Top guest favorite

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, 130 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 favorite

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.

Guesthouse 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 favorite

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, 115 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 favorite

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, 172 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 favorite

A rustic cottage with a thatched roof is surrounded by a lush garden. Large windows provide views of the greenery. Sunlight casts gentle shadows on the lawn, where friendly animals can be seen roaming freely.

Farm stay in Winterton

4.94 out of 5 average rating, 68 reviews

Guinea Cottage - Schiet Drift Farm - Winterton

Guinea Cottage is a remote, self-catering unit situated on Schiet Drift, a working farm on the the banks of the mighty Tugela River. Fishing is available on the farm. We love animals, so you will definitely find a friendly, wet nose coming up close to you. Geese and chickens roam around the homesteads freely. Come for an off-the-beaten-track-NO WiFi-farm experience. This remote, rustic but very cozy one-bedroomed cottage is 18km from Winterton, 15km of which is via a dirt road.

Top guest favorite

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, 53 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.

Superhost

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, 102 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.

Guest favorite

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, 374 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 favorite

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

4.96 out of 5 average rating, 90 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.

Guest favorite

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, 84 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..

Superhost

A picturesque view of rolling green hills and the Drakensberg mountain range under a blue sky with scattered clouds. A gravel path leads through the landscape, bordered by lush vegetation and a few structures in the distance.

Home in Central Drakensberg

4.86 out of 5 average rating, 228 reviews

Dragon View Estate, Central Drakensberg

Set on a private eco-estate. Dragon View Estate is situated in the heart of the much loved, Champagne Valley. Centrally located close to family-friendly activities including 2 golf courses, hiking, the reptile centre, the extreme adventure centre, Drakensberg Boys Choir, Bakeries and Restaurants. A Saverite grocery store is also available a couple of Kms away. Great for families, and larger groups.

Guest favorite

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, 174 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.