Windsor Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Where to stay in Windsor
Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Invercargill City Centre
3 out of top 10 points of interest in this area
Unique features of Invercargill City Centre include the theaters and bars. Make a stop by Civic Theatre or Classic Motorcycle Mecca while you're exploring the area.
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 Bill Richardson Transport World or Surrey Park.
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 Civic Theatre or Classic Motorcycle Mecca.
Glengarry
2 out of top 10 points of interest in this area
Travelers like the parks in Glengarry, and Surrey Park is a top attraction you might want to visit.
Georgetown
2 out of top 10 points of interest in this area
Travelers like the parks in Georgetown, and Rugby Park Stadium is a top attraction you might want to visit.
Windsor Hotel Deals
Windsor Haven - A cosy Home away from Home
Invercargill Southland Region
CA $169
CA $248 total
Aug 26 - Aug 27
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 Jul 16, 2026
Heart of Windsor
Invercargill Southland
CA $221
CA $333 total
Aug 20 - Aug 21
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 Jan 2, 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 Mar 19, 2026
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 vacation package cost?
From as little as . Yes, you read that right. Our Windsor vacation 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 vacation 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 vacation?
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 vacation 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 organizing a beach break in a villa or would rather stay in a cozy apartment in the city, Expedia can help make it happen.
Can I choose my airline with a Windsor Expedia vacation 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 vacation package?
Yes, you can. We understand that life happens, so we're happy to help if you need to make changes to your Windsor vacation 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.
Things to do
Bill Richardson Transport World Museum Ticket
CA $37
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.