Simon's Town Vacation Packages

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Your Simons Town Vacation

Book a tailored Simons Town vacation package that has everything you need and no unnecessary extras. Good for watersports, nature and skiing, think about basing yourself in the neighborhood of Scarborough. Make your trip to Simons Town even more fulfilling by including some sightseeing. Boulders Beach, Fish Hoek Beach and Kalk Bay Beach are among the most popular attractions you'll want to explore. Don't put off visiting this destination any longer. Your dream Simons Town vacation is only a few clicks away with Expedia.

Top Holiday Package Deals in Simon's Town

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

Caline VIP Mews

3 out of 5
Price was CA $2,800, price is now CA $2,649 per person
CA $2,649
per person
Jun 24 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cape Town (CPT)
2/10 (2 reviews)
O' Two Hotel

O' Two Hotel

4 out of 5
Mouille Point
Price was CA $4,004, price is now CA $3,536 per person
CA $3,536
per person
Jun 24 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cape Town (CPT)
9.2/10 Wonderful! (68 reviews)
Really lovely stay, everyone was so helpful and friendly. A great location for morning walks and coffee, we could see the dolphins from our balcony.

Reviewed on Apr 15, 2026

Zevenwacht Wine Estate

Zevenwacht Wine Estate

4 out of 5
Kuils River
Price was CA $2,970, price is now CA $2,763 per person
CA $2,763
per person
Jun 24 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cape Town (CPT)
8.4/10 Very Good! (21 reviews)
Very roomy cottage, staff is nice. Breakfast is great. Cleaning crew did an excellent job of cleaning the cottage. Only issue was no air-conditioning.

Reviewed on Dec 27, 2025

Medindi Manor

Medindi Manor

3.5 out of 5
Mowbray
Price was CA $3,052, price is now CA $2,872 per person
CA $2,872
per person
Jun 24 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cape Town (CPT)
9.8/10 Exceptional! (33 reviews)
I cannot begin to express the level of hospitality the staff has spills upon me. They were thorough, kind, informative and I’ve already recommended them to friends and relatives who will be making their way to Cape Town within the next month or so.

Reviewed on Mar 23, 2026

Canopy By Hilton Cape Town Longkloof

Canopy By Hilton Cape Town Longkloof

4 out of 5
Cape Town City Centre
Price was CA $3,580, price is now CA $3,382 per person
CA $3,382
per person
Jun 25 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Cape Town (CPT)
9.8/10 Exceptional! (33 reviews)
Clean and new amenities, nice breakfast, friendly staff

Reviewed on Feb 12, 2026

Where to stay in Simon's Town

Find the best Simon's Town areas and neighborhoods for the activities you enjoy most. Learn more about Simon's Town
Victoria and Alfred Waterfront

Victoria and Alfred Waterfront

Explore the oldest working harbour in the Southern Hemisphere, offering shopping, dining, and attractions like Battery Park, the 1882 clock tower, and Zeitz MOCAA contemporary art museum.

Find hotels in Victoria and Alfred Waterfront

Simon's Town Hotel Deals

Penguins View Guesthouse

Penguins View Guesthouse

4 out of 5
1 Bellevue Road Cape Town Western Cape
10/10 Exceptional! (46 reviews)
The room itself is nice, but not fancy. The view, however, is spectacular and overlooks the golf course on one side, and a view of False Bay on the other. Right up from Penguin Beach, and about a mile from the main drag with all of the shops.

Reviewed on Apr 11, 2026

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Penguins View Guesthouse
Simon's Town Quayside Hotel

Simon's Town Quayside Hotel

3 out of 5
Jubilee Square St Georges Street Cape Town Western Cape
The price is CA $97 per night from Apr 28 to Apr 29
CA $97
CA $111 total
Apr 28 - Apr 29
includes taxes & fees
9/10 Wonderful! (328 reviews)
This is a must stay when going to Simmons Town

Reviewed on Mar 13, 2026

Simon's Town Quayside Hotel
Taj Cape Town

Taj Cape Town

5 out of 5
1 Wale Street Cape Town Western Cape
Fully refundableReserve now, pay when you stay
The price is CA $276 per night from Apr 20 to Apr 21
CA $276
CA $321 total
Apr 20 - Apr 21
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
This is my overall pick for Cape Town, South Africa. The staff goes above and beyond to make you feel at home and just spoiled rotten. The hotel was very clean from the dining areas and rooms to the gym facility. I can't rave enough about this place! The food was incredible! Definitely 5 star quailty ...

Reviewed on Apr 15, 2026

Taj Cape Town
See all 4,920 properties in Simon's Town
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 a Simons Town vacation package cost?
Be ready to book, because a getaway to Simons Town starts from only CA $2,649. When you bundle your hotels, flights and car rentals into a vacation package, you'll walk away with the biggest deals.
How do I get a cheap travel package to Simons Town?
Browse and lock in everything in the one place with our Simons Town vacation packages. You'll find deals on flights, hotels and more that'll keep your hip pocket happy and your adventurous spirit full. And, with more than 550 partner airlines and 1,000,000 properties globally to choose from, you'll have the flexibility to mix and match as you want.
Where should I stay in Simons Town?
With interesting attractions like Boulders Beach and Simons Town Museum in this neighborhood, look for a hotel situated near either one. Fishermans Beach is another sight that pulls the crowds.
What are the top hotels in Simons Town?
Get your escape off to a good start by booking a stay at Magellan's Passage. It's one of most sought-after properties in Simons Town. Another leading option is Penguins View Guesthouse.
How far in advance should I book my Simons Town vacation?
It can be tricky to know when the best time is to book your vacation to Simons Town. But generally the earlier you book, the cheaper the prices. In some cases, you can lock in your flights and hotels up to 12 months prior to departure. If you're thinking of a last-minute getaway, no need to stress! There are fabulous bargains posted on Expedia every single day.
What does an Expedia Simons Town travel package include?
You can choose from a combination of flights, rental cars and hotels. Once you've made your booking, you can add the fun stuff like tours and activities. Want to pick your fare class? That's easily done too. The choice is all yours when it comes to putting together your dream Simons Town escape.
What should I know before booking a Simons Town travel package?
So many places to travel to, so many things to do. With a travel package, you can check more of them off your list. Bundle your hotels, flights and rental cars and score big savings.
Can I choose my airline with a Simons Town Expedia vacation package?
You can, and with over 550 airlines to pick from across the globe, you're spoiled for choice. Look through the available options and see which airline best fits your budget and needs.
If I'm not able to travel, can I cancel my Simons Town vacation package?
You can cancel your Simons Town booking if your plans have changed. Whether you'll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to cancel or change your booking for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Simon's Town

Boulders Beach

Boulders Beach

Get a privileged close-up view of an African penguin colony among the spectacular rock formations at this beach that also offers excellent swimming conditions.

Boulders Beach

Things to do

Kayak to the penguins in Simons Town

Kayak to the penguins in Simons Town

CA $49
per adult
Kayak to the penguins in Simons Town
Cape Town Full Day Table Mountain, Cape Point & Winelands Tour

Cape Town Full Day Table Mountain, Cape Point & Winelands Tour

CA $193
per traveller
100% of travellers recommend
Cape Town Full Day Table Mountain, Cape Point & Winelands Tour
Cape Town: Great African Sea Forest Guided Snorkel

Cape Town: Great African Sea Forest Guided Snorkel

CA $99
per adult
Cape Town: Great African Sea Forest Guided Snorkel
See all activities in Cape Town

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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.