Winchester Hills Vacations from $406

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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.

Midrand Conference Centre

Midrand

$406

per person

Oct 15 - Oct 19

found 2 days ago

Roundtrip flight included

Harare (HRE) to Johannesburg (JNB)

7.6/10 Good! (45 reviews)

Good safe hotel with excellent staff. Extremely close to the Gallagher conference center and perfect for exhibitors/visitors to the show.

Reviewed on Sep 11, 2026

Hyde Johannesburg Rosebank

Rosebank

$707

per person

Oct 15 - Oct 19

found 1 day ago

Roundtrip flight included

Harare (HRE) to Johannesburg (JNB)

9.6/10 Exceptional! (241 reviews)

The Residence Boutique Hotel

Houghton Estate

$3,149

per person

Oct 31 - Nov 6

found 7 hours ago

Roundtrip non-stop flight included

Atlanta (ATL) to Johannesburg (JNB)

9.8/10 Exceptional! (308 reviews)

Never have been disappointed staying here. Great staff, excellent food, great piano player, comfortable rooms

Reviewed on Apr 28, 2026

Golden Impalas Bush Resort

$1,697

per person

Nov 23 - Nov 28

found 1 hour ago

Roundtrip flight included

New York (NYC) to Johannesburg (JNB)

10/10 Exceptional! (4 reviews)

Really beautiful experience. We stayed in the suites. Your own pool braai and fire pit. Spacious rooms, beautiful bathrooms. Lovely kitchen. You can do self catering , or there is a lovely restaurant.

Reviewed on May 17, 2026

Fairlawns Boutique Hotel and Spa

Sandton

$1,690

per person

Nov 15 - Nov 17

found 21 hours ago

Roundtrip flight included

New York (NYC) to Johannesburg (JNB)

9.6/10 Exceptional! (110 reviews)

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.

A paved path in a park surrounded by dense green foliage.

Randburg

Unique features of Randburg include the golf courses and gardens. Make a stop by Emmarentia Dam or Cresta Shopping Centre while you're exploring the area.

Winchester Hills Hotel Deals

City Lodge Hotel at OR Tambo International Airport

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

$139 nightly

$161 total

Oct 7 - Oct 8

Total with taxes and fees

Southern Sun O.R Tambo

Airport Grounds, Jones Road, / Kempton Park Gauteng

Fully refundableReserve now, pay when you stay

$131 nightly

$155 total

Sep 26 - Sep 27

Total with taxes and fees

8.6/10 Excellent! (1,638 reviews)

"The hotel is ok. Shuttle worked well, gym was great, food ok and staff in the restaurant were gruff, rushed and spilt food on us due to their lack of care when clearing the table. While house keeping cleaned the clothes super fast, the whole situation could have been avoided if slow and steady (and ..."

Reviewed on Sep 13, 2026

Sandton Sun & Towers

Cnr. Fith And Alice Streets Johannesburg Gauteng

Fully refundableReserve now, pay when you stay

$196 nightly

$228 total

Oct 5 - Oct 6

Total with taxes and fees

See all 2,965 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.