Windsor Holidays

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Your Windsor Holiday

Your next great escape is calling with a holiday package to Windsor. Fun, food and nonstop great times — you're sure to find it in this neighbourhood. When it's time to see the sights, you'll find a lot of big-name attractions nearby including Civic Theatre, Bill Richardson Transport World and Stadium Southland. Tick off one, two or all during your trip to Windsor. Stop dreaming and start doing. When it's time to lock in your next holiday to Windsor, Expedia will help you get there.

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

A historic clock tower with a statue on top, surrounded by a landscaped garden and a road intersection.

Invercargill City Centre

5 out of top 10 points of interest in this area

Unique features of Invercargill City Centre include the theatres and bars. Make a stop by Civic Theatre or Toetoes Bay while you're exploring the area.

Richmond

Richmond is well liked for its parks. If you'd like to do some sightseeing in the greater Invercargill area, you might plan a trip to Rugby Park Stadium or Civic Theatre.

Georgetown

1 out of top 10 points of interest in this area

Travellers like the parks in Georgetown, and Rugby Park Stadium is a top attraction you might want to visit.

A historic tower with a dome, surrounded by lush greenery and a clear sky.

Turnbull Thompson Park

Turnbull Thompson Park is well liked for its parks. If you'd like to do some sightseeing in the greater Invercargill area, you might plan a trip to Rugby Park Stadium or Bill Richardson Transport World.

Appleby

Appleby is noteworthy for its spas, and you can plan an outing to Rugby Park Stadium and Civic Theatre while you're in town.

Our pick of the best Windsor Hotel Deals

Windsor Haven - A cosy Home away from Home

Invercargill Southland Region

AU$242

26 Oct - 27 Oct

includes taxes & fees

9.6/10 Exceptional! (5 reviews)

"Ideal for 2 adults & 2 children. Heat pump keeps the whole unit cosy. Parking was suitable for a large SUV or 2 small cars. Everything was spotlessly clean without you getting the feeling you don't want to touch anything. Well appointed with all the kitchen equipment. The only possible drawback is ..."

Reviewed on 16 July 2026

Cosy and Warm. Centrally located to all Invercargill has to offer.

Invercargill Southland

9/10 Wonderful! (12 reviews)

"Lovely warm clean cosy house with everything you need for a great stay in Southland.Proximity to good shops and eateries a plus .Excellent hosts who care."

Reviewed on 19 Mar 2026

Get rates

Heart of Windsor

Invercargill Southland

AU$335

27 Sept - 28 Sept

includes taxes & fees

8.8/10 Excellent! (3 reviews)

"The houses location was good and access to the key was easy. The kitchen was modern. Had a comfortable living area. The hot water pressure was lacking."

Reviewed on 2 Jan 2026

See all 105 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.

Frequently asked questions

How much does a Windsor holiday package cost?

From as little as . Yes, you read that right. Our Windsor holiday packages are an awesome way to make your budget stretch further. Bundle your preferred flights, hotels and rental car and get out and see this destination your way.

How do I get a cheap travel package to Windsor?

You'll save a ton of money if you bundle your flights, car rentals and hotels into a Windsor holiday package. Sometimes cheap means fewer options. But not with Expedia. We offer more than 550 airlines and 1 000 000 properties all over the world, which means you'll always have plenty of options to choose from. Eager to save even more? Add some interesting activities to your package deal and unlock even bigger discounts! After all, travel is about more than simply getting to your destination.

Where should I stay in Windsor?

We recommend staying near the action. Many visitors favor hotels around popular attractions, such as Southland Hospital, Bill Richardson Transport World and Stadium Southland.

How far in advance should I book my Windsor holiday?

It can be hard to know when is the ideal time to book your Windsor trip. But generally the earlier you book, the cheaper the prices. In some cases, you can lock in your flights and hotels nearly a year prior to departure. If you're hoping for a last-minute getaway, no need to fret! There are great bargains featured on Expedia every single day.

What does an Expedia Windsor travel package include?

From airfares and hotels to rental cars, Expedia can help you put together a Windsor package that's perfect for you. Heading away for a week or two? Give some thought to a flight, hotel and rental car bundle. If you're taking a short break, a hotel and flight deal may suit you better. 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?

When you book your hotels, flights and car rentals together, you'll pick up amazing discounts. Whether you're organising a beach break in a villa or would rather stay in a cosy apartment in the city, Expedia can help make it happen.

Can I choose my airline with a Windsor Expedia holiday package?

Yes, and with more than 550 airlines to choose from across the globe, you have plenty of choice. Look through the available options and find out which airline best suits your budget and needs.

If I'm not able to travel, can I cancel my Windsor holiday package?

Yes, you can. We understand that life happens, so we're happy to help if you need to make changes to your Windsor holiday package. You may be able to cancel or amend your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may impose a fee if you booked more than 24 hours ago. Head to our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.