Windsor Holidays from AU$2,146

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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.
CT Hotel

CT Hotel

5 out of 5
Arcadia
per person
18 Oct - 24 Oct
just found
Return direct flight included
Sydney (SYD) to Johannesburg (JNB)
8.4/10 Very Good! (415 reviews)
Formerly the Sheraton. Staff were great. The property was dated. Someone jumped into the elevator who was not a hotel guest and propositioned me. Luckily he got off before I reached my room floor, but it was unsettling.

Reviewed on 10 May 2025

The Peech Hotel

The Peech Hotel

4 out of 5
per person
18 Oct - 24 Oct
just found
Return direct flight included
Sydney (SYD) to Johannesburg (JNB)
9.8/10 Exceptional! (118 reviews)
Highly recommend the Peech Hotel in Johannesburg. Absolutely beautiful grounds and accommodations at this boutique hotel. The staff was outstanding and the 2 onsite restaurants were great.

Reviewed on 17 May 2025

The Leonardo

The Leonardo

5 out of 5
Sandton
per person
18 Oct - 24 Oct
just found
Return direct flight included
Sydney (SYD) to Johannesburg (JNB)
9.2/10 Wonderful! (48 reviews)
Exceptional unit and beautiful building, lobby and amenities. Great location close to Mandela Square, Sandton City. Buffet breakfast was quite average compared to the otherwise exceptional unit, building and service.

Reviewed on 6 Jan. 2025

Hyde Johannesburg Rosebank

Hyde Johannesburg Rosebank

4 out of 5
Rosebank
per person
18 Oct - 24 Oct
just found
Return direct flight included
Sydney (SYD) to Johannesburg (JNB)
9.6/10 Exceptional! (129 reviews)
Beautiful design, spacious rooms, excellent breakfast and very friendly staff!

Reviewed on 19 Jul. 2025

The Houghton Hotel, Spa, Wellness & Golf

The Houghton Hotel, Spa, Wellness & Golf

5 out of 5
Houghton Estate
per person
18 Oct - 24 Oct
just found
Return direct flight included
Sydney (SYD) to Johannesburg (JNB)
9.4/10 Exceptional! (196 reviews)
Good, large property with plenty parking and in a quiet neighborhood. Dining options are few and there’s no shopping onsite, but you can drive to different areas easily. Rooms are modern and well built.

Reviewed on 5 Aug. 2025

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
Default Image

Sandton

4 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, OR Tambo International Airport, Kempton Park, Gauteng
The price is AU$205 per night from 7 Sept to 8 Sept
AU$205
7 Sept - 8 Sept
includes taxes & fees
8.8/10 Excellent! (1,709 reviews)
"The room was nice and beds good but unfortunately the dinner was discusting. I took the special South African dish and the beef was not fresh, the sausage not fully cooked, the chicken a little smelly. I should have returned the whole meal but the vegetables and fries were okay and we were ..."

Reviewed on 7 Aug. 2025

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

Premier Hotel OR Tambo

4 out of 5
73 Gladiator Street, Rhodesfield, Kempton Park, Gauteng
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 7 Sept to 8 Sept
AU$185
7 Sept - 8 Sept
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Layover in Joburg en route to Zambia. I would love to return for a visit to South Africa and stay in this hotel!"

Reviewed on 7 Aug. 2025

Premier Hotel OR Tambo
@Sandton Hotel

@Sandton Hotel

3 out of 5
5 Benmore Rd, Sandton, Gauteng
Fully refundableReserve now, pay when you stay
The price is AU$161 per night from 25 Aug to 26 Aug
AU$161
25 Aug - 26 Aug
includes taxes & fees
9.2/10 Wonderful! (241 reviews)
"Great Staff, great food. Love the safe location"

Reviewed on 8 Aug. 2025

@Sandton Hotel
See all 2,396 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

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$2,146. 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

Johannesburg city

Half-Day Johannesburg City Tour with Pickup

AU$153
per adult
Half-Day Johannesburg City Tour with Pickup
Johannesburg Full-Day Tou

Johannesburg Full-Day Tour(Soweto/Jo-Burg & Apartheid Museum)

AU$210
per adult
100% of travellers recommend
Johannesburg Full-Day Tour(Soweto/Jo-Burg & Apartheid Museum)
Johannesburg, Apartheid Museum & Soweto

Johannesburg, Apartheid Museum & Soweto

AU$291
per adult
Johannesburg, Apartheid Museum & Soweto
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.