Winchester Hills Vacations from $524

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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.

The Latest Winchester Hills Vacation Packages

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

Europrime Hotels Airport

$524

per person

Nov 28 - Dec 2

found 1 day ago

Roundtrip flight included

Bulawayo (BUQ) to Johannesburg (JNB)

8.2/10 Very Good! (242 reviews)

Great place

Reviewed on Sep 28, 2026

Fairlawns Boutique Hotel and Spa

Sandton

$1,097

per person

Dec 4 - Dec 7

found 19 hours ago

Roundtrip flight included

Bulawayo (BUQ) to Johannesburg (JNB)

9.6/10 Exceptional! (113 reviews)

The Residence Boutique Hotel

Houghton Estate

$1,067

per person

Nov 28 - Dec 2

found 1 day ago

Roundtrip flight included

Bulawayo (BUQ) to Johannesburg (JNB)

9.8/10 Exceptional! (308 reviews)

African Rock Hotel & Spa, a "Boutique Lifestyle Resort"

$1,244

per person

Nov 28 - Dec 2

found 1 day ago

Roundtrip flight included

Bulawayo (BUQ) to Johannesburg (JNB)

10/10 Exceptional! (39 reviews)

The Leonardo

Sandton

$935

per person

Dec 4 - Dec 7

found 19 hours ago

Roundtrip flight included

Bulawayo (BUQ) to Johannesburg (JNB)

9.4/10 Exceptional! (72 reviews)

Excelente as always, restaurant needs to look at its menu.

Reviewed on Sep 28, 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

A modern glass building with a reflective facade, surrounded by a cityscape and distant hills.

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.

A cityscape with a prominent cylindrical skyscraper, a stadium, and surrounding residential and commercial buildings.

Rosebank

1 out of top 10 points of interest in this area

Rosebank is known for its ample dining options, and you can make a stop by Rosebank Mall and The Zone @ Rosebank Shopping Center while in the area.

A tree-lined street with purple flowers.

O.R. Tambo

1 out of top 10 points of interest in this area

While visiting O.R. Tambo, you might make a stop by sights like International Terminal Duty Free Mall and Emperors Palace Casino.

An aerial view of a residential area with houses, winding roads, and a river.

Midrand

1 out of top 10 points of interest in this area

You'll enjoy the gardens and spas in Midrand. You might want to make time for a stop at Mall of Africa or Kyalami Racetrack.

Two large cooling towers with colorful murals, surrounded by trees and power lines.

Soweto

You'll enjoy the museums and churches in Soweto. You might want to make time for a stop at Maponya Mall or Mandela's House.

Winchester Hills Hotel Deals

City Lodge Hotel at OR Tambo International Airport

Above Multi-Storey Parkade 2, Level 5 Kempton Park Gauteng

$143 nightly

$165 total

Nov 11 - Nov 12

Total with taxes and fees

Sandton Sun & Towers

Cnr. Fith And Alice Streets Johannesburg Gauteng

Fully refundableReserve now, pay when you stay

$137 nightly

$159 total

Oct 18 - Oct 19

Total with taxes and fees

Southern Sun O.R Tambo

Airport Grounds, Jones Road, / Kempton Park Gauteng

Fully refundableReserve now, pay when you stay

$104 nightly

$120 total

Nov 10 - Nov 11

Total with taxes and fees

8.6/10 Excellent! (1,644 reviews)

"With the renovations going on it was a little difficult to find the smoking area around the pool"

Reviewed on Oct 15, 2026

See all 3,003 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.