Vacation rentals in Helderberg Mountain

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Top-rated vacation rentals in Helderberg Mountain

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Guest favorite

Farm stay in Stellenbosch

Annandale Wines Farm Cottage, Stellenbosch

Escape to a quaint farm house just outside Stellenbosch.This charming retreat offers rustic character, beautiful vineyards and mountain views. Book a wine tasting at Annandale, enjoy delicious meals at our restaurant &fill your pantry with fresh produce from the on-site farm stall Familiér. Wander the vineyards, picnic at the farm dam in or enjoy a South African braai on the patio. Perfectly located for exploring the area, this is the ideal spot to unwind and experience true countryside living.

4.9 out of 5 average rating, 31 reviews

Top guest favorite

Farm stay in Stellenbosch

Farmstay for nature lovers Jonkershoek

A tranquil farm stay set against Jonkershoek’s breathtaking mountains, ideal for a couple seeking peace and nature. Relax in a spacious, comfortable furnished home with a wood‑burning stove and outdoor space tucked between old oaks. Explore trails, swim in the farm dam, or unwind with wine on the deck. Minutes drive from Stellenbosch’s vibrant food and wine scene and University campus, yet feels worlds apart. Perfect for a peaceful escape or longer stay for a creative and mindful work retreat.

4.99 out of 5 average rating, 120 reviews

Top guest favorite

A spacious deck features a wood-fired hot tub surrounded by wooden planters, complemented by comfortable outdoor chairs. Lush greenery fills the background, enhancing the tranquil setting. Sunlight illuminates the area, creating a warm atmosphere for relaxation.

Farm stay in Stellenbosch

Hidden gem in the heart of the winelands..

A little forest in the heart of the Winelands cuddles this secret gem #jangroentjiecottage close to a dam fed by the fynbos covered Helderberg. a Selfcatering hideaway that sleeps two with a fireplace, braai and a woodfired hottub. Within walking distance from Taaibosch, Pink Valley and Avontuur Wine and stud farm. Just across the R44 Ken Forrester Wines is luring. For the outdoor enthusiasts Helderberg provide trails for hiking and mtbiking and our dam covers swimming, rowing and sundowners.

5.0 out of 5 average rating, 270 reviews

Guest favorite

An outdoor area features a rectangular pool surrounded by a wooden deck. Comfortable loungers are arranged nearby, complemented by decorative cushions. Sliding glass doors lead to the indoor living space, with greenery visible in the background.

Home in Somerset West

Beautiful, kid-friendly home with views and pool

Modern, spacious, very comfortable family home. INVERTER BACK UP POWER. Perfect outdoor area including BBQ facilities, pizza oven, a glorious pool and comfortable loungers to a spacious but cozy indoor lounge area with fireplace and open plan kitchen. Plenty of room and entertainment for kids with an outdoor play area including jungle gym as well as kids bedroom with single bed, an extra sleeper sofa and also a travel cot with mattress (bring own linen for travel cot) A/C in 2 bedrooms only.

4.87 out of 5 average rating, 112 reviews

Top guest favorite

A charming cottage is nestled within a lush garden, showcasing a patio adorned with plants. The surrounding greenery includes a manicured lawn and a pathway leading to the entrance. Mature trees provide shade, enhancing the tranquil atmosphere of the outdoor space.

Cottage in Somerset West

Cranberry Cottage - A place for the soul

Relax, unwind, and enjoy the peaceful surroundings of Cranberry Cottage tucked away in the beautiful Helderberg Basin. Have the convenience of your own separate entrance, secure undercover parking and the comfort of a fully equipped home and private entertainment/barbecue area. You are in a quiet, private treed haven close to restaurants, nature parks, wine estates, golf course, Strand beach and hiking trails amongst many other amenities that Somerset West and its surrounds has to offer.

5.0 out of 5 average rating, 101 reviews

Superhost

A spacious living area features curved seating, inviting relaxation. Floor-to-ceiling windows provide panoramic views of the city and mountains. A sleek television is mounted on the wall, with minimalist decor enhancing the open layout. Natural light illuminates the room, creating a calm environment.

Apartment in Strand

3 Bed Beachfront Paradise!

If you're looking to unwind with family or friends, our sea side apartment offers the perfect spot to do so. Book now! and let us share our little piece of paradise with you. Features: 2.4 KVA battery backup to run TV, lights etc Fast 5G WiFI Smart TV, Netflix, Disney, Showmax etc Large open living spaces Full Kitchen - 5 Burner Gas Hob Swimming Pool Please reach out if you have any special requirements! 25min CT Int Airport 20min Stellenbosch 40min Cape Town CBD 60min Hermanus

4.91 out of 5 average rating, 122 reviews

Top guest favorite

A dining area features a large wooden table surrounded by woven chairs, with modern pendant lighting overhead. Floor-to-ceiling glass walls offer expansive views of the landscape, allowing natural light to fill the space and create a bright atmosphere.

Villa in Somerset West

Glorious views, amazing sunsets!

Come and relax in the lap of luxury and unsurpassed beauty! This stunning 4 bedroom contemporary house was designed and decorated by a renowned German designer. European chic is combined with subtle ethnic and earthy interior to create a truly unique ambiance! UPS power backup for Wifi, lights and essential plugs during loadshedding. The stove and air conditioners will not be operational during loadshedding. Airconditioners available in all living areas and in 3 of the 4 bedrooms.

4.91 out of 5 average rating, 76 reviews

Guest favorite

Condo in Johannesdal

Villa Verde, farm stay with views for days.

Enjoy a peaceful farm stay at Villa Verde, gallery and guesthouse in the Cape Winelands. Stay in your own private studio apartment right in the heart of the winelands between Stellenbosch and Franschhoek. Views are spectacular and the infinity pool is welcoming you on the warm summer days. Pick your own seasonal fruits in our garden and explore the variety of restaurants, wineries and hundreds of hikes and mountain bike paths close by. Perfect for families and couple get aways.

5.0 out of 5 average rating, 24 reviews

Guest favorite

Home in Stellenbosch

Bellevlei Estate | The Rock House

Welcome to our spacious, independent and stylish 1-bedroom retreat, located on the Blauwklippen road just minutes from Stellenbosch. The Rock House is perfect for taking in the sights of the historical town of Stellenbosch, mountain biking trails or a quick round of golf. Although shops and restaurants are only a five-minute drive away, the area feels peaceful and secluded. Whether you're here for a weekend getaway or a longer stay, the Rock House has all that you need.

4.89 out of 5 average rating, 111 reviews

Guest favorite

A tree-lined pathway is flanked by lush greenery and vibrant autumn foliage. Solar lamps on either side illuminate the walkway leading towards rolling hills in the background, showcasing solid greenery and a clear blue sky.

Guest suite in Cape Winelands District Municipality

Helderbosch The View Self-Catering Accommodation

This cosy 2-bedroom unit features a queen-size bed in the main bedroom and two three-quarter beds in the second bedroom. The bathroom boasts both a shower and a bath, with an additional guest toilet conveniently located off the lounge area. The open-plan living and dining area leads to a fully equipped kitchen, offering plenty of space for your stay. Both bedrooms and the living area open onto a private patio, complete with braai facilities and stunning views.

4.98 out of 5 average rating, 122 reviews

Top guest favorite

A warm living area is highlighted by an exposed brick wall and wooden beams. A comfortable brown leather sofa is paired with a green chair, while a coffee table sits over the polished concrete floor. A small television is positioned across from the seating area, with a view of an adjacent bedroom.

Home in Stellenbosch

Farm house on Windon vineyard,Stellenbosch

This beautiful farm house has amazing views of the Stellenbosch mountain ranges .It has a very special indigenous garden and is beautifully decorated and equipped! It includes a full kitchen ,2 beautiful rooms and en suite bathrooms .There is a beautiful patio and braai area .It is a peaceful setting ,with access to walk and enjoy the farm including the zebra and springbuck ! You won’t be sorry you booked this magnificent spot ,you won’t ever want to leave !

5.0 out of 5 average rating, 104 reviews

Guest favorite

A contemporary residence presents a blend of modern architecture and natural surroundings. Walls are adorned in neutral tones, framed by lush gardens and mature trees. The backdrop features the gently sloping Stellenbosch mountains, creating a serene atmosphere in the outdoor space.

Home in Stellenbosch

Farm Keerweer Manor House

Nestled at the foot of the Stellenbosch mountains, rich in its history and perfectly located along a crystal-clear river, within the tranquil surrounds of old oak trees, many over 100 years and along lush gardens, is a beautiful contemporary 2 bedroom 2 bathroom residence. The entire farm runs on solar power so guests can enjoy their stay without worrying about the current "load shedding" time to unwind and ensure your stay is one of relaxation and pleasure.

5.0 out of 5 average rating, 34 reviews