Overstrand Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Top vacation destinations in Overstrand

View towards Hermanus and the Kleinrivier Mountains from Klipgat Cave. De Kelders (or Die Kelders). Whale Coast. Western Cape. South Africa
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Gansbaai

Gansbaai

Top Overstrand Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Beulah Lodge

Beulah Lodge

3 out of 5
Pinelands
Price was CA $2,580, price is now CA $2,478 per person
CA $2,478
per person
May 19 - May 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Cape Town (CPT)
10/10 Exceptional! (2 reviews)
This property is so beautiful, clean, and great place to stay. I will certainly stay here again and Highly recomend it

Reviewed on Dec 10, 2025

VILLA PUCCINI

VILLA PUCCINI

4 out of 5
Claremont
Price was CA $3,184, price is now CA $2,850 per person
CA $2,850
per person
May 19 - May 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Cape Town (CPT)
10/10 Exceptional! (2 reviews)
The accommodation at Villa Puccini is brilliant with its ability to capture a cozy yet exquisite experience, settled comfortably within Cape Town suburbs. The rooms each offer their own unique fashion and have the amenities for a proper stay away from home.

Reviewed on Oct 18, 2022

Taj Cape Town

Taj Cape Town

5 out of 5
Cape Town City Centre
Price was CA $3,146, price is now CA $2,820 per person
CA $2,820
per person
Jun 4 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Cape Town (CPT)
9.4/10 Exceptional! (1,009 reviews)
Great hotel in a central location. Close to major attractions. Staff were all fantastic

Reviewed on Apr 12, 2026

Paperbark Manor

Paperbark Manor

4 out of 5
Plattekloof
Price was CA $2,743, price is now CA $2,625 per person
CA $2,625
per person
May 19 - May 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Cape Town (CPT)
10/10 Exceptional! (18 reviews)
Lovely view of table top mountain with wonderful large room

Reviewed on Mar 4, 2026

Wild Olive Guest House

Wild Olive Guest House

4 out of 5
Claremont
Price was CA $3,011, price is now CA $2,886 per person
CA $2,886
per person
May 19 - May 29
found 20 hours ago
Roundtrip flight included
Toronto (YTO) to Cape Town (CPT)
9.6/10 Exceptional! (92 reviews)
We thoroughly enjoyed every minute and every aspect of our stay at the Wild Olive. The food was amazing and the staff genuinely friendly and kind. You'll not regret the decision to spend your holiday here!

Reviewed on Nov 14, 2025

Overstrand Hotel Deals

Whale Coast All Suite Hotel

Whale Coast All Suite Hotel

4 out of 5
c/o Lord Roberts & Royal Roads Hermanus Western Cape
The price is CA $101 per night from Apr 23 to Apr 24
CA $101
CA $116 total
Apr 23 - Apr 24
includes taxes & fees
9.2/10 Wonderful! (251 reviews)
The 3 bedroom apartment is large and has a balcony with a braai. The main bedroom has it own bathroom (bath and shower) while the other bedrooms share a bathroom (shower only) via the passage upstairs. There is a WC downstairs in the living space and large kitchen. There is a great view of the mountains. ...

Reviewed on Apr 8, 2026

Whale Coast All Suite Hotel
Esplanade Hermanus

Esplanade Hermanus

63 Marine Dr Hermanus Western Cape
The price is CA $264 per night from Apr 27 to Apr 28
CA $264
CA $264 total
Apr 27 - Apr 28
includes taxes & fees
9.6/10 Exceptional! (102 reviews)
View from the room was amazing , walking distance to all restaurants and shops

Reviewed on Apr 8, 2026

Esplanade Hermanus
Misty Waves Boutique Hotel

Misty Waves Boutique Hotel

4 out of 5
21 Marine Drive Hermanus Western Cape
The price is CA $141 per night from Apr 23 to Apr 24
CA $141
CA $165 total
Apr 23 - Apr 24
includes taxes & fees
9/10 Wonderful! (262 reviews)
The staff at this hotel are very professional and helpful; this was our third time staying there. The room was very clean and the hotel is really lovely. It is situated directly across from the sea. There is a restaurant onsite, but we did not eat there.

Reviewed on Apr 10, 2026

Misty Waves Boutique Hotel
See all 429 properties in Overstrand
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.
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Frequently asked questions

How much does an Overstrand vacation package cost?
Our Overstrand packages, which start from just CA $2,478, are an ideal way to save big bucks. Choose your favorite flights, hotels and rental cars to create your perfect trip.
How do I get a cheap travel package to Overstrand?
One of the simplest ways to save cash (and time) is to combine your bookings with Expedia. Flights, rental cars, hotels and activities — we've got them all. Pick and choose a combination that best fits you and see your savings pile up. We know a package deal is never one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 properties globally, which lets you customize your Overstrand adventure.
How far in advance should I book my Overstrand vacation?
It can be difficult to know exactly when the best time is to book your Overstrand trip. But generally the earlier you book, the cheaper the prices. In some cases, you can book your flights and hotels nearly 12 months before departure. If you're thinking of a last-minute getaway, no need to stress! There are incredible deals posted on Expedia every single day.
What does an Expedia Overstrand travel package include?
From airfares and hotels to rental cars, Expedia can help you put together an Overstrand package that's perfect for you. Heading off for a few weeks? Give some thought to a hotel, flight and rental car bundle. If your break is short, a hotel and airfare deal could be more your style. Tours and activities can be added once you've made your booking. Our vacation packages make it easy to save and plan.
What should I know before booking an Overstrand travel package?
A travel package can be customized for your circumstances and is a simple way to make your hard-earned dollars stretch further. How much you include is up to you. Rental cars, hotels and flights — choose any combination that suits your plans.
Can I choose my airline with an Overstrand Expedia vacation package?
Expedia has access to more than 550 airline partners worldwide, so you certainly can. Just select your favorite carrier and put together the perfect Overstrand trip.
If I'm not able to travel, can I cancel my Overstrand vacation package?
Don't stress if you're rethinking your Overstrand vacation package — you can cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur fees from your hotel, airline or car rental company. We realize life can sometimes throw you a curveball, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.