Cape Winelands Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

Top Beach vacation packages in Cape Winelands

Price found within the past 48 hours. Click for updated prices.
Khashamongo B&B

Khashamongo B&B

Somerset West
$887
per person
Oct 25 - Oct 30
found 1 day ago
Roundtrip flight included
Harare (HRE) to Cape Town (CPT)
8.4/10 Very Good! (7 reviews)
They are not accommodating at all I booked for myself and my 11 year old and 15 year old. Conning from the USA about 5 hours away I got they don’t allow kids under 16 and I have to pay extra for them to stay there. No where does that say it on the booking form or info page. Then got told I should be luck to get a refund. Would not recommend this place at all

Reviewed on Oct 15, 2024

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Find your perfect Cape Winelands beach vacation

How do I book the best Cape Winelands beach vacation packages?

Life’s a beach when you dive into our brilliant Cape Winelands beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Cape Winelands?

A rental steps from the shore creates an amazingly affordable Cape Winelands beach vacation. Seaside sojourns during low season start from $887. Prices and availability are subject to change. Additional terms may apply.

How can I book the best family beach vacations in Cape Winelands?

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Cape Winelands beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Cape Winelands vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Cape Winelands beach vacation deals?

Sort your search results by deals to delight in amazing Cape Winelands beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Cape Winelands beach trip with free cancellation and/or flexible dates?

Just like the Cape Winelands tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Cape Winelands beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Cape Winelands. (OK, maybe not that last part.)

Top Beach Cape Winelands Hotels

Oude Werf Hotel

Oude Werf Hotel

30 Church Street Stellenbosch Western Cape
  • 25 min drive from Boschendal Estate
Book a stay at this family-friendly hotel in Stellenbosch. Enjoy free WiFi, free parking, and room service. Our guests praise the helpful staff in our reviews. ...
9.2/10 Wonderful! (365 reviews)
"Lovely hotel, lovely staff would recommend"

Reviewed on Aug 3, 2026

Oude Werf Hotel
Krystal Beach Hotel

Krystal Beach Hotel

Breakwater Lane, Harbour Island Cape Town Western Cape
  • 52 min drive from Boschendal Estate
Come and relax at this spa hotel and get ready to enjoy the sunsets on the beach in Cape Town, as you'll be near the beach. 3 restaurants, 2 bars, and a full-service ...
9/10 Wonderful! (308 reviews)

Travelers like: close to beach, outdoor pool

Travelers say...
"wonderful stay with friendly staff and great food and service. great value for money"

Reviewed on Sep 16, 2026

Krystal Beach Hotel
One Marine Drive Boutique Hotel

One Marine Drive Boutique Hotel

1 Marine Drive Hermanus Western Cape
  • 2 hours drive from Boschendal Estate
Book a stay at this luxury hotel in Hermanus. Enjoy free WiFi, breakfast (surcharge), and an airport shuttle (surcharge). Popular attractions Whale Museum and ...
9.6/10 Exceptional! (178 reviews)
"This really is a classy boutique hotel. Well positioned. Beautifully appointed. Friendly and attentive staff. Can't fault it!"

Reviewed on Sep 6, 2026

One Marine Drive Boutique Hotel
See all 2,323 properties in Cape Winelands
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Things to do

From Stellenbosch: Hop-On Hop-Off Wine Tour Southern Route

From Stellenbosch: Hop-On Hop-Off Wine Tour Southern Route

$30
per adult
100% of travellers recommend
From Stellenbosch: Hop-On Hop-Off Wine Tour Southern Route
Walking Tour of Stellenbosch

Walking Tour of Stellenbosch

$19
per adult
Walking Tour of Stellenbosch
Full Day Afrivista Wine Tours from Stellenbosch

Full Day Afrivista Wine Tours from Stellenbosch

$119
per adult
Full Day Afrivista Wine Tours from Stellenbosch
See all activities in Cape Winelands

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.