Winterstrand Vacations from $2,197

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Your Winterstrand Vacation

Book a custom vacation package to Winterstrand and start looking forward to your next epic adventure. Base yourself in the neighborhood of Nahoon, which is good for surfing and coastal beaches, for a real taste of this captivating city. There's lots to see and do during your trip to Winterstrand, including Cove Rock and Alexander Country Club. Whoever you're heading away with and whatever your bank balance, your ultimate Winterstrand vacation is only clicks away with Expedia.

The Latest Winterstrand vacation packages

Price found within the past 48 hours. Click for updated prices.
Beachwalk Bed and Breakfast

Beachwalk Bed and Breakfast

4 out of 5
Summerstrand
Price was $2,218, price is now $2,197 per person
$2,197
per person
Dec 10 - Dec 12
found 1 day ago
Roundtrip flight included
Omaha (OMA) to Port Elizabeth (PLZ)
9.4/10 Exceptional! (114 reviews)
Clean and comfortable, very safe and two block walking distance to restaurants and mall overlooking the ocean. Nice pool and owners are very welcoming and live on site! Enjoy!

Reviewed on Dec 28, 2024

No5 Boutique Art Hotel by Mantis

No5 Boutique Art Hotel by Mantis

4.5 out of 5
Summerstrand
Price was $3,334, price is now $3,276 per person
$3,276
per person
Dec 17 - Dec 19
found 1 day ago
Roundtrip flight included
Omaha (OMA) to Port Elizabeth (PLZ)
9.6/10 Exceptional! (81 reviews)
This is a real gem! Fantastic boutique hotel with beautiful rooms that roomy and quiet. All the amenities you could ever need. The breakfast was delicious with lots of options. You really need to stay more than one night to get to see what it has to offer.

Reviewed on Mar 19, 2023

The Kelway Hotel

The Kelway Hotel

3 out of 5
Summerstrand
Price was $2,232, price is now $2,197 per person
$2,197
per person
Dec 10 - Dec 12
found 1 day ago
Roundtrip flight included
Omaha (OMA) to Port Elizabeth (PLZ)
8.4/10 Very Good! (181 reviews)
Great place to stay, breakfast was nice. Could do with some more vegan options for breakfast and something in the resturant for the eveningh

Reviewed on Feb 17, 2025

Brighton Lodge

Brighton Lodge

4 out of 5
Summerstrand
Price was $3,212, price is now $3,177 per person
$3,177
per person
Dec 17 - Dec 19
found 1 day ago
Roundtrip flight included
Omaha (OMA) to Port Elizabeth (PLZ)
9.4/10 Exceptional! (20 reviews)
Only stayed one night but Brighton Lodge is a comfortable and pleasantly quirky place to stay. All the staff were lovely and helpful but Claudette in particular was a cheerful joy.

Reviewed on Jan 4, 2025

Amery House

Amery House

4 out of 5
Summerstrand
Price was $3,209, price is now $3,181 per person
$3,181
per person
Dec 17 - Dec 19
found 1 day ago
Roundtrip flight included
Omaha (OMA) to Port Elizabeth (PLZ)
9.6/10 Exceptional! (23 reviews)
This is a lovely guest house with wonderful hosts. We cannot say enough about the great hospitality, spacious room, beautiful gardens, and delicious breakfast. The guest house is in a quiet neighborhood, but it was so easy and inexpensive to get Ubers to take us anywhere we wanted to go in town. Our stay exceeded every single one of our expectations. We would highly recommend this is a place to stay if you want to enjoy the peaceful tranquility of the area, yet be a very short drive to dining and the beach.

Reviewed on Mar 7, 2025

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Winterstrand Hotel Deals

Beachfront Inn

Beachfront Inn

Winterstrand
Get rates
Beachfront Inn
Premier Hotel East London ICC

Premier Hotel East London ICC

4 out of 5
22 Esplanade, Beachfront, East London, Eastern Cape
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $80 total per night from Oct 17 to Oct 18
$80 total
Oct 17 - Oct 18
Total with taxes and fees
8.2/10 Very Good! (335 reviews)
"The staff really makes this property! I would highly recommend for that alone but love my stays at ICC. Easy, well located and impeccable service. The food and beverage deserves a special recommendation as a team!"

Reviewed on Oct 5, 2025

Premier Hotel East London ICC
Premier Hotel Regent

Premier Hotel Regent

3 out of 5
22 Esplanade, Beach Front, East London, Eastern Cape
Fully refundableReserve now, pay when you stay
$57 nightly
The price is $65 total per night from Nov 1 to Nov 2
$65 total
Nov 1 - Nov 2
Total with taxes and fees
7.2/10 Good! (96 reviews)
"I really enjoyed a room that overlooked the Indian Ocean. The staff was very helpful and responsive when a need arose."

Reviewed on Sep 28, 2024

Premier Hotel Regent
See all 118 properties in Winterstrand
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.

Winterstrand Essential Information

Language
Afrikaans
Currency
South African rands
Closest Airport
East London Airport (ELS)
Max Temp Winter
70ºF
Max Temp Summer
75ºF
Top Sights
Eastern Beach, Nahoon Beach and Kidds Beach

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Frequently asked questions

How much does a Winterstrand vacation package cost?
Offering excellent value package deals from $2,197 on Expedia, you'll be thrilled with how little a vacation to Winterstrand costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winterstrand?
You can usually find lower rates and better availability in February, May and December. Explore our cheap Winterstrand vacation packages and you could score some great off-season deals.
How many days is enough for Winterstrand?
Usually, a handful of days is enough to see the top sights during your Winterstrand vacation. But if you prefer to have time to relax or take day tours, think about extending your trip.
How to find the best Winterstrand package deals?
Bagging a cheap Winterstrand package deal is a breeze with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most affordable Winterstrand package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book a Winterstrand vacation as a package?
An Expedia vacation package could score you significant savings when compared to booking flights and hotels individually. Better still, you can tailor your Winterstrand getaway to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Explore our bundles to see how much you can save.
When to book a vacation package to Winterstrand?
Land incredible discounts by booking your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Winterstrand adventure.
Does Expedia offer Book Now, Pay Later Winterstrand vacation packages?
Your Winterstrand getaway is meant to be an escape from your busy life, not a reason for money worries. So to give you a bit more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and split up the cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.