Winchester Hills Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Your Winchester Hills Vacation

Lock in a Winchester Hills vacation package that has everything you need without any unnecessary extras. Good for bars and pubs, markets and nightlife, think about basing yourself in the neighborhood of Rosebank. A trip to Winchester Hills is a terrific opportunity to sightsee. Be sure to visit popular attractions like Gold Reef City Casino, Apartheid Museum and First National Bank Stadium. Whoever you're escaping with and whatever you plan to spend, your ultimate Winchester Hills vacation is just a few clicks away with Expedia.

Top Holiday Package Deals in Winchester Hills

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

Lido Hotel

3.5 out of 5
Johannesburg South
Price was CA $875, price is now CA $802 per person
CA $802
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Mumbai (BOM) to Johannesburg (JNB)
7.2/10 Good! (41 reviews)
This location is outside of the city, not much to do in the area, during my 1 night stay there was no wi-fi and the staff did nothing to solve the problem.

Reviewed on Jun 9, 2025

Apollo Hotel

Apollo Hotel

3 out of 5
Randburg
Price was CA $940, price is now CA $846 per person
CA $846
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Mumbai (BOM) to Johannesburg (JNB)
8.2/10 Very Good! (90 reviews)
Waterkloof Apartments

Waterkloof Apartments

3 out of 5
Waterkloof
Price was CA $954, price is now CA $885 per person
CA $885
per person
Apr 19 - Apr 25
found 1 day ago
Roundtrip non-stop flight included
Mumbai (BOM) to Johannesburg (JNB)
9.8/10 Exceptional! (11 reviews)
Beautifully appointed apartment with very comfortable beds and clean facilities. Easy and flexible check-in and great communication with staff.

Reviewed on Apr 7, 2024

The Houghton Hotel, Spa, Wellness & Golf

The Houghton Hotel, Spa, Wellness & Golf

5 out of 5
Houghton Estate
Price was CA $3,163, price is now CA $2,592 per person
CA $2,592
per person
May 21 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Johannesburg (JNB)
9.4/10 Exceptional! (222 reviews)
Great room, courteous and efficient staff, first rate.

Reviewed on Dec 17, 2025

Sandton Sun & Towers

Sandton Sun & Towers

5 out of 5
Sandton
Price was CA $2,234, price is now CA $2,024 per person
CA $2,024
per person
May 21 - May 26
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Johannesburg (JNB)
9.2/10 Wonderful! (577 reviews)
Lovel hotel. Beustaff great - the desk manager helped us select and book day trip outside of the JoBurg

Reviewed on Feb 5, 2026

Where to stay in Winchester Hills

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

Sandton

4 out of top 10 points of interest in this area

A noteworthy feature of Sandton is its popular shops. While you're in town, be sure to stop and check out Nelson Mandela Square and Sandton City Mall.

Find hotels in Sandton

Winchester Hills 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 CA $205 per night from Apr 5 to Apr 6
CA $205
CA $237 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (1,876 reviews)
I just went to my room, ate in the Resturant and flew out the next morning… very confident and clean…

Reviewed on Mar 5, 2026

City Lodge Hotel at OR Tambo International Airport
Southern Sun O.R Tambo

Southern Sun O.R Tambo

4 out of 5
Airport Grounds, Jones Road, / Kempton Park Gauteng
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Apr 4 to Apr 5
CA $153
CA $176 total
Apr 4 - Apr 5
includes taxes & fees
8.6/10 Excellent! (1,642 reviews)
Property was pleasant but does need some refurbishing since it was starting to look a little outdated. Buffet breakfast was excellent.

Reviewed on Mar 5, 2026

Southern Sun O.R Tambo
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 CA $121 per night from Mar 15 to Mar 16
CA $121
CA $141 total
Mar 15 - Mar 16
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Everything was excellant

Reviewed on Feb 26, 2026

Premier Hotel OR Tambo
See all 2,400 properties in Winchester Hills
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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Winchester Hills vacation package cost?
From as low as CA $802, you can create your own Winchester Hills vacation package. Simply bundle flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Winchester Hills?
Combining your hotel and flight with Expedia won't just save you time — it'll save you a nice amount too. A Winchester Hills vacation package makes it easy to create the perfect trip. With more than 550 airlines worldwide to choose from, finding flights that suit your schedule won't be a challenge. Not only that, we have over 1,000,000 hotels globally to choose from. Now that's choice! Whatever your budget, Expedia brings the world within your reach.
Where should I stay in Winchester Hills?
Most people who travel to Winchester Hills put both Gold Reef City and Apartheid Museum on their sightseeing itineraries. Why not choose a hotel that's close to these iconic attractions?
What are the top hotels in Winchester Hills?
Winchester Lodge is one of Winchester Hills's most sought-after properties. Secure a room here and you'll be able to sleep soundly knowing you're in excellent hands.
How far in advance should I book my Winchester Hills vacation?
It's tricky picking the ideal time for airfares, but we generally suggest the earlier, the better. Plenty of international flights on Expedia become available up to 12 months in advance. If you're booking at the last minute, don't fret. Bargain prices appear from time to time just weeks before departure dates.
What does an Expedia Winchester Hills travel package include?
Expedia has everything you need to book your Winchester Hills getaway, but how your package is structured is your call. Choose from any combination of hotels, flights and rental cars. In search of some activities to keep you on the go? Once you've made your booking, you can add them on too. Whatever your budget or style, there's a package deal to suit your needs.
What should I know before booking a Winchester Hills travel package?
You'll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and score fabulous discounts. You're not restricted to hotels, though. Book with us and choose from beachside condos, rural cottages and just about everything in between!
Can I choose my airline with a Winchester Hills Expedia vacation package?
Yes, and with more than 550 airlines to pick from all over the world, you're not short on choice. Look through the available options and see which airline best suits your budget and needs.
If I'm not able to travel, can I cancel my Winchester Hills vacation package?
Don't stress if you're rethinking your Winchester Hills vacation package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We know life can sometimes throw you a curveball, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we're ready to help.

Discover the most popular places to visit in Winchester Hills

Gold Reef City which includes a city, 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
Great food, drinks and vibe.

Sandton City Mall

During your visit to Johannesburg, you can enjoy retail therapy at Sandton City Mall. You can attend a sporting event while in the area.

Sandton City Mall
Apartheid Museum featuring 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

Things to do

Soweto: Guided Bicycle Tour with Lunch

Soweto: Guided Bicycle Tour with Lunch

CA $73
per adult
Soweto: Guided Bicycle Tour with Lunch
Hartbeespoort Dam: The Luxury Alba Boat Cruise with Food

Hartbeespoort Dam: The Luxury Alba Boat Cruise with Food

CA $72
per adult
Hartbeespoort Dam: The Luxury Alba Boat Cruise with Food
From Johannesburg: Rhino & Lion Safari and Wonder Cave Tour

From Johannesburg: Rhino & Lion Safari and Wonder Cave Tour

CA $167
per adult
From Johannesburg: Rhino & Lion Safari and Wonder Cave Tour
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.