Herolds Bay Vacations from $1,348

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Your Herolds Bay Vacation

From its highlights to its hidden gems, this city is best experienced with a Herolds Bay vacation package. Find somewhere to stay in Great Brak River, which is good for culture, views and history. Oubaai Golf Estate, Kingswood Golf Estate and The Links are just some of the attractions worth checking out during your trip to Herolds Bay. Stop daydreaming and start adventuring. Browse the wide range of options on Expedia today and finally put your Herolds Bay vacation plans into action!

The Latest Herolds Bay vacation packages

Price found within the past 48 hours. Click for updated prices.
@Franschhoek Hotel

@Franschhoek Hotel

3.5 out of 5
Price was $1,645, price is now $1,348 per person
$1,348
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Cape Town (CPT)
9.4/10 Exceptional! (45 reviews)
Everyone made us feel very welcome. We had one small issue at the start and it was quickly taken care of.

Reviewed on Apr 17, 2025

O' Two Hotel

O' Two Hotel

4 out of 5
Sea Point Promenade
Price was $2,219, price is now $1,685 per person
$1,685
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Cape Town (CPT)
9.6/10 Exceptional! (49 reviews)
Cute boutique. Lobby smelled great. Jug of ice cold water flavored with lemon or cucumbers or strawberries, nice touch. Great decor. Staff friendly and receptive and helpful. The room although small had great windows, view of golf course. Terrace view of ocean. Shower very hot which was outstanding. . Thin walls could hear shower next door. Terrace close together could smell smoke from room next door. Would prefer no smoking Period.

Reviewed on Jul 13, 2025

Labotessa Luxury Boutique Hotel

Labotessa Luxury Boutique Hotel

5 out of 5
Cape Town City Centre
Price was $3,184, price is now $2,554 per person
$2,554
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Cape Town (CPT)
9.8/10 Exceptional! (37 reviews)
The staff at this charming, boutique establishment were the most welcoming and helpful I have ever encountered, with a level of service and hospitality exceeding any reasonable expectations.

Reviewed on Jul 26, 2025

Lawhill Luxury Apartments

Lawhill Luxury Apartments

5 out of 5
Victoria and Alfred Waterfront
Price was $3,177, price is now $2,549 per person
$2,549
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Washington (WAS) to Cape Town (CPT)
9.2/10 Wonderful! (162 reviews)
Have stayed here before and it is very comfortable and good value for money

Reviewed on Jun 23, 2025

Atlantic Palms

Atlantic Palms

4.5 out of 5
Sunset Beach
Price was $2,475, price is now $2,033 per person
$2,033
per person
Oct 22 - Oct 27
found 4 hours ago
Roundtrip non-stop flight included
New York (NYC) to Cape Town (CPT)
9.2/10 Wonderful! (9 reviews)
Nice get away hotel with charme. Directly at the beach with pool. Not everything is perfect but I prefer real humans around me.

Reviewed on Aug 22, 2025

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Discover the most popular places to visit in Herolds Bay

Oubaai Golf Estate

Enjoy a round of golf in Herolds Bay at Oubaai Golf Estate. You can enjoy the restaurants while in the area.

Oubaai Golf Estate

Freesia Spa

You can take time to visit Freesia Spa during your travels to Herolds Bay. You can enjoy the restaurants while in the area.

Freesia Spa

Herolds Bay Hotel Deals

Oubaai Hotel Golf & Spa

Oubaai Hotel Golf & Spa

4 out of 5
406 Herolds Bay Road, Herolds Bay, Western Cape
$56 nightly
The price is $64 total per night from Sep 8 to Sep 9
$64 total
Sep 8 - Sep 9
Total with taxes and fees
Oubaai Hotel Golf & Spa
Dutton's Cove Guesthouse

Dutton's Cove Guesthouse

3 out of 5
21 Rooidraai Avenue, Herolds Bay, Western Cape
Get rates
Dutton's Cove Guesthouse
Makarios on Sea

Makarios on Sea

4 out of 5
4 Gericke's Corner, Garden Route, Herolds Bay, Western Cape
$123 nightly
The price is $142 total per night from Sep 8 to Sep 9
$142 total
Sep 8 - Sep 9
Total with taxes and fees
Makarios on Sea
See all 294 properties in Herolds Bay
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 Herolds Bay vacation package cost?
Offering great value package deals from $1,348 on Expedia, you'll be surprised at how little a vacation to Herolds Bay costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Herolds Bay?
You can generally find reduced prices and better availability in May, November and December. Browse our cheap Herolds Bay vacation packages and you could score some great off-season discounts.
How many days is enough for Herolds Bay?
Generally, a handful of days is enough to see the top sights during your Herolds Bay vacation. But if you want to have some time to unwind or take day trips, think about extending your itinerary.
How to find the best Herolds Bay package deals?
Finding a cheap Herolds Bay package deal is a breeze with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a few filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most pocket-friendly Herolds Bay package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Herolds Bay vacation as a package?
You can enjoy significant savings on your Herolds Bay escape by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to see some great airfares and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Herolds Bay?
Land incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, grab one of our last-minute deals for a spur-of-the-moment Herolds Bay break.
Does Expedia offer Book Now, Pay Later Herolds Bay vacation packages?
Set off on your perfect escape to Herolds Bay with help from Expedia's Book Now, Pay Later vacations. No need to save up or wait until the next payday — we've partnered with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans allow you to spread the cost over 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to budget for your trip and snap up bargains before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.