Windsor Holidays from AU$2,177

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Your Windsor Holiday

Booking a tailor-made Windsor holiday package is an excellent way to get to know this neighbourhood. From its must-visit places to its little-known gems, you'll be sure to uncover something new. Begin your trip to Windsor with a visit to nearby attractions such as Cresta Shopping Centre, Randpark Golf Club and Northcliff Ridge Ecopark. Don't just imagine it — make it a reality! Book your perfect Windsor holiday with Expedia and enjoy travelling your way.

Top Holiday Package Deals in Windsor

Price found within the past 48 hours. Click for updated prices.
Hyde Johannesburg Rosebank

Hyde Johannesburg Rosebank

4 out of 5
Rosebank
Price was AU$2,383, price is now AU$2,177 per person
AU$2,177
per person
17 Mar - 22 Mar
found 5 hours ago
Return direct flight included
Sydney (SYD) to Johannesburg (JNB)
9.6/10 Exceptional! (151 reviews)
Just awesome all around

Reviewed on 31 Dec 2025

Peermont Mondior At Emperors Palace

Peermont Mondior At Emperors Palace

4 out of 5
O.R. Tambo
Price was AU$2,720, price is now AU$2,301 per person
AU$2,301
per person
17 Mar - 22 Mar
found 5 hours ago
Return direct flight included
Sydney (SYD) to Johannesburg (JNB)
7.8/10 Good! (312 reviews)
Everything is walking distance and under the roof, didn’t have to go outside. Loved that about the hotel. The Spa was excellent from the moment you walk in. I give all the ladies there 10/10.

Reviewed on 3 Jan 2026

The Houghton Hotel, Spa, Wellness & Golf

The Houghton Hotel, Spa, Wellness & Golf

5 out of 5
Houghton Estate
Price was AU$2,664, price is now AU$2,364 per person
AU$2,364
per person
17 Mar - 22 Mar
found 5 hours ago
Return direct flight included
Sydney (SYD) to Johannesburg (JNB)
9.2/10 Wonderful! (212 reviews)
Great room, courteous and efficient staff, first rate.

Reviewed on 17 Dec 2025

54 On Bath

54 On Bath

5 out of 5
Rosebank
Price was AU$2,784, price is now AU$2,538 per person
AU$2,538
per person
17 Mar - 22 Mar
found 5 hours ago
Return direct flight included
Sydney (SYD) to Johannesburg (JNB)
9.6/10 Exceptional! (232 reviews)
My husband and I like the convenience of not having to go outside to shop in the mall just taking the elevator to the 2nd floor. Also free breakfast was an added bonus. The front office workers, kitchen & dinner room staff were outstanding. Shout out to Penny-thank you

Reviewed on 13 May 2025

Davinci Hotel And Suites On Nelson Mandela Square

Davinci Hotel And Suites On Nelson Mandela Square

5 out of 5
Sandton
Price was AU$2,783, price is now AU$2,558 per person
AU$2,558
per person
17 Mar - 22 Mar
found 5 hours ago
Return direct flight included
Sydney (SYD) to Johannesburg (JNB)
9.2/10 Wonderful! (734 reviews)
Breakfast was excellent

Reviewed on 5 Jan 2026

Our guide on where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
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Sandton

3 out of top 10 points of interest in this area

Travellers to Sandton praise its popular shops. If you've got some more time to explore, be sure to stop by Nelson Mandela Square and Sandton City Mall.

Find hotels in Sandton

Our pick of the best Windsor Hotel Deals

City Lodge Hotel at OR Tambo International Airport

City Lodge Hotel at OR Tambo International Airport

3 out of 5
Above Multi-Storey Parkade 2, Level 5 Kempton Park Gauteng
The price is AU$227 per night from 7 Feb to 8 Feb
AU$227
7 Feb - 8 Feb
includes taxes & fees
8.8/10 Excellent! (1,844 reviews)
The room and the hotel was spotless.

Reviewed on 6 Jan 2026

City Lodge Hotel at OR Tambo International Airport
Premier Hotel OR Tambo

Premier Hotel OR Tambo

4 out of 5
73 Gladiator Street Kempton Park Gauteng
Fully refundableReserve now, pay when you stay
The price is AU$160 per night from 16 Jan to 17 Jan
AU$160
16 Jan - 17 Jan
includes taxes & fees
8.6/10 Excellent! (1,010 reviews)
Very spacious room, comfy bed, free shuttle service, smooth-ish check-in. Please upgrade the shower head and modernise your rooms... the carpets look dated. Also buffet breakfast was overpriced.

Reviewed on 5 Jan 2026

Premier Hotel OR Tambo
Southern Sun O.R Tambo

Southern Sun O.R Tambo

4 out of 5
Airport Grounds, Jones Road, / Kempton Park GP
The price is AU$188 per night from 1 Feb to 2 Feb
AU$188
1 Feb - 2 Feb
includes taxes & fees
8.6/10 Excellent! (1,659 reviews)
Nice staff

Reviewed on 4 Jan 2026

Southern Sun O.R Tambo
See all 2,531 properties in Windsor
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 Windsor holiday package cost?
Browse and book everything in one place with our Windsor holiday packages, which start from just AU$2,177. Select the hotels and flights that match your travel plans. Then, add on a few tours or experiences for an incredible getaway.
How do I get a cheap travel package to Windsor?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you dollars too. A Windsor holiday package makes it a cinch to arrange the ideal trip. With more than 550 airlines around the world to select from, finding flights that suit your schedule will be no sweat. Not only that, we have over 1 000 000 hotels globally to pick from. Now that's what we call choice. Whatever your budget, Expedia can show you the world.
Where should I stay in Windsor?
Stay where the action happens. Many travellers book hotels within easy reach of top attractions, such as Cresta Shopping Centre, Randpark Golf Club and Johannesburg Eye Hospital.
What are the top hotels in Windsor?
Get your trip off to a fantastic start by reserving a room at Isabel's Guesthouse. It's one of most sought-after hotels in Windsor. Another welcoming option is Khamanzi Lodge And Tours.
How far in advance should I book my Windsor holiday?
Search Expedia to compare international flights as soon as you've got your travel dates. In many cases, you can purchase a seat up to 12 months before departure. If you can't find your preferred carrier, or you've left things to the last minute, don't stress. The lowest prices to Windsor sometimes occur just weeks before departure.
What does an Expedia Windsor travel package include?
From airfares and hotels to car rentals, Expedia can help you create a Windsor package that's right for you. Heading away for a while? Look into a rental car, flight and hotel bundle. If your break is short, a hotel and airfare deal could be what you're after. Tours and activities can be added once you've made your booking. Our holiday packages make it a cinch to save and plan.
What should I know before booking a Windsor travel package?
You can save a tidy sum by combining your hotels, airfares and rental cars. Once you've created your package, you can add on things like activities or sightseeing tours. Your next unforgettable holiday is only a couple of clicks away.
Can I choose my airline with a Windsor Expedia holiday package?
Expedia has access to more than 550 partner airlines globally, so you certainly can. Simply choose your preferred air carrier and put together your ideal Windsor escape.
If I'm not able to travel, can I cancel my Windsor holiday package?
We totally get that life doesn't always go according to plan. If you've locked in a Windsor holiday package and have to amend or cancel it, we can help. We recommend taking a look at our Customer Service Portal first for information. But generally speaking, if you've taken out your package within 24 hours, you may be able to cancel and rebook for free. If it's more than 24 hours, your hotel, airline or car rental company may impose a charge.

Discover the most popular places to visit in Windsor

Montecasino

Montecasino

With shops, theaters and a bird park among the attractions, there’s fun for all the family during the day and night at this Tuscan-themed entertainment center.

Montecasino
Gold Reef City showing outdoor art, a statue or sculpture and art

Gold Reef City Casino

Thrilling roller coasters, a 19th-century gold mine, cultural shows and a petting zoo provide entertainment for all ages at this popular theme park.

Gold Reef City Casino
Apartheid Museum which includes art and a city

Apartheid Museum

Reflect on the impact and legacy of apartheid and learn about the contribution of Nelson Mandela and others to South Africa's new constitution.

Apartheid Museum

Activities

Soweto: Guided Bicycle Tour with Lunch

Soweto: Guided Bicycle Tour with Lunch

AU$81
per adult
Soweto: Guided Bicycle Tour with Lunch
From Johannesburg: Lion & Safari Park Half-Day Tour

From Johannesburg: Lion & Safari Park Half-Day Tour

AU$210
per adult
From Johannesburg: Lion & Safari Park Half-Day Tour
Soweto Walking Tour with Lunch

Soweto Cultural Walking Tour with Lunch

AU$70
per adult
Soweto Cultural Walking Tour with Lunch
See all activities in Johannesburg
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.