Overstrand Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top vacation destinations in Overstrand

A coastal landscape with rocky formations, clear turquoise waters, and distant mountains.
FlightsFlightsHotelsHotels

Gansbaai

Gansbaai

Top Overstrand Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Caline VIP Mews

Caline VIP Mews

3 out of 5
Price was CA $2,468, price is now CA $2,258 per person
CA $2,258
per person
Oct 1 - Oct 10
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Cape Town (CPT)
2/10 (2 reviews)
The accommodation was nothing like the pictures. The neighbourhood felt unsafe. There was not 5 pools as per the description. We ended up leaving within the hour and staying somewhere else.

Reviewed on Jan 7, 2026

Kilima Franschhoek

Kilima Franschhoek

5 out of 5
Price was CA $3,863, price is now CA $2,996 per person
CA $2,996
per person
Aug 16 - Aug 21
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Cape Town (CPT)
10/10 Exceptional! (2 reviews)

The Spier Hotel

The Spier Hotel

4 out of 5
Price was CA $3,842, price is now CA $3,227 per person
CA $3,227
per person
Aug 16 - Aug 21
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Cape Town (CPT)
9.2/10 Wonderful! (580 reviews)
I loved this wine farm ! I found it online and booked and the only thing I regretted was our stay was only two nights ! I will definitely stay here again if I return to stellenbosch !

Reviewed on Apr 13, 2026

Zevenwacht Wine Estate

Zevenwacht Wine Estate

4 out of 5
Kuils River
Price was CA $2,980, price is now CA $2,652 per person
CA $2,652
per person
Oct 1 - Oct 10
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Cape Town (CPT)
8.6/10 Excellent! (23 reviews)

Cresta Grande Cape Town

Cresta Grande Cape Town

4 out of 5
Cape Town City Centre
Price was CA $3,181, price is now CA $2,909 per person
CA $2,909
per person
Oct 1 - Oct 10
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Cape Town (CPT)
8.8/10 Excellent! (104 reviews)
Quiet and good location. Breakfast good and friendly staff. Beds comfortable but terrible pillows. Way too large/thick for any woman and no thinner ones available

Reviewed on May 27, 2026

Overstrand Hotel Deals

Esplanade Hermanus

Esplanade Hermanus

63 Marine Dr Hermanus Western Cape
The price is CA $209 per night from Jul 28 to Jul 29
CA $209
CA $209 total
Jul 28 - Jul 29
includes taxes & fees
9.6/10 Exceptional! (106 reviews)
"Stayed in a 1BR 1BA recently remodeled room with kitchen, stove, oven, refrigerator, and dishwasher, and washer/dryer. Sea view room with balcony was great place to enjoy morning coffee while watching the bay. Did see whales. Secure parking garage with CCTV, motion activated lights, and security ..."

Reviewed on Jun 26, 2026

Esplanade Hermanus
Whale Coast All Suite Hotel

Whale Coast All Suite Hotel

4 out of 5
c/o Lord Roberts & Royal Roads Hermanus Western Cape
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Jul 28 to Jul 29
CA $191
CA $220 total
Jul 28 - Jul 29
includes taxes & fees
9.2/10 Wonderful! (259 reviews)
"The photos are deceptive, the hotel is on the second story of a shopping mall. We struggled to find it as the directions said to go in the mall car park, signage and directions for the ‘hotel’ were hopeless. The room and bed itself were comfortable but the view was over a mall car park. The security ..."

Reviewed on Jun 2, 2026

Whale Coast All Suite Hotel
The Marine Hermanus

The Marine Hermanus

5 out of 5
Marine Drive Hermanus Western Cape
The price is CA $454 per night from Jul 28 to Jul 29
CA $454
CA $529 total
Jul 28 - Jul 29
includes taxes & fees
The Marine Hermanus
See all 451 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Overstrand vacation package cost?
Our Overstrand packages, which start from just CA $2,258, 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.

Stay near popular Overstrand attractions

Harold Porter National Botanical Gardens

9.6/10 (7 reviews)
Explore the great outdoors at Harold Porter National Botanical Gardens, a lovely green space in Betty's Bay. Discover the spas in this relaxing area, or seek out its golf courses.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.