Cape Winelands Holiday Rentals from AU$145: Search Short-Term Rentals

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Our top choices for Cape Winelands holiday rentals

A wooden deck with a table set for dining, a grill, and a brick wall with sliding glass doors.

1. Lands Edge Eco Friendly Cottages

Struisbaai

Denis

includes taxes & fees

14 Oct - 15 Oct

A swimming pool with lounge chairs and umbrellas, surrounded by a wooden deck and a bonsai tree.

2. A Riverbed Guesthouse

Swellendam

Neil

includes taxes & fees

23 Oct - 24 Oct

A person holding a tray with two drinks by a pool with a view of a lake and hills.

3. De Hoop Collection

Overberg

Matthias

includes taxes & fees

16 Oct - 17 Oct

An outdoor patio with a wooden table and chairs, a hanging light fixture, and a view of a mountainous landscape.

4. Kingfisher Cottages

Montagu

includes taxes & fees

20 Oct - 21 Oct

An aerial view of a coastal town with a large parking lot, a prominent building with a flat roof, and a road leading to the sea.

5. Whale Coast All Suite Hotel

Hermanus City-Centre

Glenn

includes taxes & fees

4 Nov - 5 Nov

A white building with a grey roof, surrounded by a white fence, set against a backdrop of yellow fields and green hills under a clear blue sky.

6. Landmeterskop

Stanford

includes taxes & fees

14 Oct - 15 Oct

A modern house with a pool, surrounded by greenery and mountains.

7. The Barn on 62

Montagu

includes taxes & fees

14 Oct - 15 Oct

A modern dining area with tables and chairs, large windows with a view of the sea, and hanging wicker lamps.

8. The Shark Bay Private Villas

Langebaan

Rhoma

includes taxes & fees

15 Oct - 16 Oct

A modern kitchen with white cabinetry, a large island, and bar stools.

9. Middedorp Villa and Apartments

Stellenbosch Central

Sayna

includes taxes & fees

24 Oct - 25 Oct

A cozy living room with a wooden ceiling, a dining area with a table and chairs, a sofa, and a window with blinds.

10. Dassenheuwel Farm Cottages

Malmesbury

includes taxes & fees

15 Oct - 16 Oct

A spacious bedroom with a large bed, wooden beams, a desk, and a fireplace.

11. Sunset Farm Stellenbosch

Stellenbosch

Stefan

includes taxes & fees

15 Oct - 16 Oct

A modern house with a stone facade, large windows, and a patio with a table and chairs.

12. Wildebraam Berry Estate

Swellendam

Herb

includes taxes & fees

27 Oct - 28 Oct

A vineyard with rows of grapevines leading to a white building with a dark roof.

13. Monkscowl Estate

Stellenbosch

includes taxes & fees

28 Oct - 29 Oct

A rocky shoreline with waves crashing against the rocks.

14. First Group Hermanus Beach Club

Westcliff

includes taxes & fees

20 Oct - 21 Oct

A vineyard estate with multiple white buildings, including a large house and several smaller structures, surrounded by lush greenery and a mountainous backdrop.

15. Endless Vineyards at Wildekrans Wine Estate

Bot River

JULIAN

includes taxes & fees

14 Oct - 15 Oct

A coastal town with white buildings, a sandy beach, and a clear blue sky.

16. Speelhuis Studios

Langebaan

Liezel

A room with a wooden door, two black chairs, a desk with a computer, and a window with blinds.

17. Zeederberg Corner

Paarl

Ryan

includes taxes & fees

14 Oct - 15 Oct

An open wooden window with a view of a forested hillside.

18. African Hut

Tulbaghweg

includes taxes & fees

14 Oct - 15 Oct

A balcony with a view of the beach and ocean, featuring a table with a striped tablecloth and a glass bowl.

19. Ashley on the Beach

Strand

Robert

includes taxes & fees

19 Oct - 20 Oct

A covered porch with two white chairs, a small table, and a birdcage.

20. Spacious 2-bedroom apartment in Riviersonderend

Riviersonderend

includes taxes & fees

14 Oct - 15 Oct

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Top Cape Winelands Hotel Reviews

The Stellenbosch Hotel

10/10 Excellent

"Comfortable, clean, friendly staff"

Misty Waves Boutique Hotel

10/10 Excellent

"Beautiful hotel with stunning sea views, wish we had stayed longer. Misty Waves was one of the standout hotels of our South African trip. Although we only stayed for one night, we left wishing we had booked longer to enjoy both the hotel and spend more time exploring Hermanus itself. The whole property is beautiful, with a relaxed boutique feel and stunning views. Our room was exceptionally spacious, beautifully decorated and overlooked the sea, making it a real highlight of our stay. The reception staff were friendly, welcoming and very helpful throughout. Combined with the quality of the accommodation and location, it made for a memorable stay that we would happily recommend to anyone visiting Hermanus."

The Marine Hermanus

10/10 Excellent

"This was my second excellent stay at the Marine Hotel. The first time could've been a fluke, but this second stay and the outstanding service and warmth of the staff proved that five star service is the absolute norm at this oustanding property and the management is clearly strong. I had a girls trip and two ocean facing rooms. Two of my friends this was a first visit to Africa and one of them had a lot of serious medical challenges (organ transplants and cancer survivor). For her, we needed a lot of bottles of distilled water for medical care and the Marine stepped up without any questions!! The tears of relief in my friends eyes, who is so used to searching for this critical medical need anytime she travels, was worth the booking alone. But the staff went out of their way to make the trip special. Patrick gave us a wonderful overview of the hotel and rooms and tips on whale watching that exceeded our expectations. The rooms were lovely, comfortable and beautifully appointed with every amenity (love the Africology products). Food in the restaurants was outstanding as well as the friendly service. The location is superb - WE HEARD WHALES breathing from our room when the window was open!! The location on the Cliff Walk is stunning. When visiting Hermanus this is the only place I will stay. If you have a chance to book an ocean view room, or just stay at this hotel, do not miss it!!! It was a universal favorite amongst my girlfriends - hands down and two thumbs up!!! Love love!"

Find out more about Cape Winelands

Everything you need to know about Cape Winelands holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cape Winelands holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cape Winelands holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search.

Cape Winelands holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cape Winelands. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cape Winelands holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cape Winelands holiday rentals we have selected for you start as low as AU$145 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Cape Winelands rentals

At Expedia, we put the best Cape Winelands holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cape Winelands rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cape Winelands holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cape Winelands. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Cape Winelands Holiday Rentals

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Check prices for these dates

Our top choices for Cape Winelands holiday rentals

1. Lands Edge Eco Friendly Cottages

2. A Riverbed Guesthouse

3. De Hoop Collection

4. Kingfisher Cottages

5. Whale Coast All Suite Hotel

6. Landmeterskop

7. The Barn on 62

8. The Shark Bay Private Villas

9. Middedorp Villa and Apartments

10. Dassenheuwel Farm Cottages

11. Sunset Farm Stellenbosch

12. Wildebraam Berry Estate

13. Monkscowl Estate

14. First Group Hermanus Beach Club

15. Endless Vineyards at Wildekrans Wine Estate

16. Speelhuis Studios

17. Zeederberg Corner

18. African Hut

19. Ashley on the Beach

20. Spacious 2-bedroom apartment in Riviersonderend

Find holiday rentals that suit your style

Top Cape Winelands Hotel Reviews

The Stellenbosch Hotel

Find out more about Cape Winelands

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