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A lighthouse on a hill with a sunset and scattered clouds.

Pringle Bay

Vacations
Pringle Bay

Overstrand flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Charles Hope Boutique Hometel

Charles Hope Boutique Hometel

4.5 out of 5
Cape Town City Centre
Price was CA $2,723, price is now CA $2,454 per person
CA $2,454
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Cape Town (CPT)
Book a stay at this luxury aparthotel in Cape Town. Enjoy free WiFi, an outdoor pool, and breakfast (surcharge). Popular attractions Long Street and Cape Town Stadium are located nearby.
The Sir David Boutique Guest House

The Sir David Boutique Guest House

4 out of 5
Bloubergstrand
Price was CA $2,871, price is now CA $2,539 per person
CA $2,539
per person
Aug 13 - Aug 16
found 22 hours ago
Roundtrip flight included
Calgary (YYC) to Cape Town (CPT)
Book a stay at this beach guesthouse in Cape Town. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Big Bay Beach and Seaside Village Shopping Centre are located nearby.
Nova Constantia Boutique Residence

Nova Constantia Boutique Residence

5 out of 5
Constantia
Price was CA $3,311, price is now CA $2,954 per person
CA $2,954
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Cape Town (CPT)
Book a stay at this luxury guesthouse in Cape Town. Enjoy free WiFi, free parking, and a full-service spa. Popular attractions Table Mountain and Constantia Wine Route are located nearby.
Cape Cadogan Boutique Hotel

Cape Cadogan Boutique Hotel

5 out of 5
Cape Town City Centre
Price was CA $3,089, price is now CA $2,786 per person
CA $2,786
per person
Sep 5 - Sep 6
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Cape Town (CPT)
Book a stay at this luxury hotel in Cape Town. Enjoy free breakfast, free WiFi, and an outdoor pool. Popular attractions Long Street and Table Mountain are located nearby.
Urban Elephant 16 on Bree

Urban Elephant 16 on Bree

4 out of 5
Cape Town City Centre
Price was CA $2,837, price is now CA $2,571 per person
CA $2,571
per person
Sep 8 - Sep 13
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Cape Town (CPT)
Book a stay at this business-friendly aparthotel in Cape Town. Enjoy free WiFi, a fitness center, and parking (surcharge). Popular attractions Long Street and Cape Town Stadium are located nearby.

Top Overstrand hotels deals

Esplanade Hermanus

Esplanade Hermanus

63 Marine Dr Hermanus Western Cape
The price is CA $218 per night
CA $218
CA $218 total
Jul 11 - Jul 12
includes taxes & fees
Stay at this hotel in Hermanus. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Whale Museum and Old Harbour are located nearby.
Pool
Parking included
Whale Coast All Suite Hotel

Whale Coast All Suite Hotel

4 out of 5
c/o Lord Roberts & Royal Roads Hermanus Western Cape
Free cancellation
Reserve now, pay when you stay
The price is CA $253 per night
CA $253
CA $291 total
Aug 1 - Aug 2
includes taxes & fees
Stay at this aparthotel in Hermanus. Enjoy free WiFi, free parking, and free bicycles on site. Popular attractions Village Square and Shopping Centre are located nearby.
Kitchen
Parking included
The Marine Hermanus

The Marine Hermanus

5 out of 5
Marine Drive Hermanus Western Cape
The price is CA $473 per night
CA $473
CA $550 total
Jul 18 - Jul 19
includes taxes & fees
Book a stay at this luxury hotel in Hermanus. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Village Square and Old Harbour are located nearby.
Pool
Spa
Misty Waves Boutique Hotel

Misty Waves Boutique Hotel

4 out of 5
21 Marine Drive Hermanus Western Cape
The price is CA $153 per night
CA $153
CA $178 total
Jul 10 - Jul 11
includes taxes & fees
Stay at this hotel in Hermanus. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Shopping Centre and Whale Museum are located nearby.
Pool
Parking included
Harbour House Hotel

Harbour House Hotel

5 out of 5
22 Harbour Road (Harbour Square) Hermanus Western Cape
The price is CA $195 per night
CA $195
CA $224 total
Jul 15 - Jul 16
includes taxes & fees
Book a stay at this luxury hotel in Hermanus. Enjoy free WiFi, free parking, and a conference center. Popular attractions Whale Museum and Old Harbour are located nearby.
Pool
Parking included
Arabella Hotel Golf & Spa

Arabella Hotel Golf & Spa

5 out of 5
R44 Kleinmond Kleinmond Western Cape
Free cancellation
Reserve now, pay when you stay
The price is CA $249 per night
CA $249
CA $286 total
Jul 16 - Jul 17
includes taxes & fees
Book a stay at this luxury hotel in Kleinmond. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions SA Forest Adventures Kleinmond and Kogelberg Biosphere Reserve are located nearby.
Pool
Hot tub
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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.

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

Photos of local treasures

Browse Overstrand vacation photos for more inspiration

A coastal path with rocky outcrops, greenery, and a distant town.
A coastal landscape with rocky cliffs, a palm tree, and mountains in the background.
A coastal road with a lighthouse, lush greenery, and yellow flowers.
A coastal road with a lighthouse in the distance, surrounded by lush greenery and yellow flowers.
A penguin standing on rocky terrain.

Frequently asked questions

How much are vacation packages to Overstrand?
Enjoy a fulfilling travel experience in Overstrand with a vacation package starting at CA $2,454. Reserving your tours, hotels and flights with Travelocity is so simple. On top of that, our packages will leave you with extra cash for fun.
Where can I get the best vacation package deals for Overstrand?
It's difficult to beat Travelocity when it comes to crafting your Overstrand package deal. There are at least 400 airlines and 1,000,000 properties around the world to choose from. Reserve your trip now and get ready to tick another place off your to-do list.
Why should I book my Overstrand vacation bundle with Travelocity?
Because we believe in creating one-of-a-kind travel experiences. From hotels and flights to car rentals and activities, we put everything at your fingertips. Our customer support is available 24/7 to make sure your needs are taken care of. We also offer a Price Match Guarantee, so you can secure your getaway knowing you've landed the best deal around. If you find a lower price, we'll match it!
Will I save money on my Overstrand car rental if I bundle it with hotels and flights?
Bundling your bookings into an Overstrand vacation package will leave you with some serious savings. Bundle a flight and car; a hotel, car and flight; or a hotel and car. There's no better way to discover the greater Overstrand region than with your own ride. You can also add experiences and tours to your Travelocity package.