Oakville Packages (Flight + Hotel)

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Where to stay in Oakville

Find the best Oakville areas and neighborhoods for the activities you enjoy most. Learn more about Oakville

Top hotels in Oakville

Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is ฿5,014 per night from 4 Aug to 5 Aug
฿5,014
฿6,148 total
4 Aug - 5 Aug
includes taxes & fees
8.2/10 Very Good! (11,649 reviews)
"A perfect location downtown Toronto. And the rooftop pool and deck area was awesome too."

Reviewed on 15 Jul 2025

Chelsea Hotel, Toronto
Fairmont Royal York

Fairmont Royal York

4 out of 5
100 Front St West, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is ฿8,721 per night from 4 Aug to 5 Aug
฿8,721
฿10,692 total
4 Aug - 5 Aug
includes taxes & fees
8.8/10 Excellent! (6,853 reviews)
"The staff were very helpful and friendly. Special thank you to customer relations staff, Alejendro and Mallory for doing their best with our special requests for our stay."

Reviewed on 14 Jul 2025

Fairmont Royal York
Holiday Inn Toronto Downtown Centre by IHG

Holiday Inn Toronto Downtown Centre by IHG

3.5 out of 5
30 Carlton Street, Toronto, ON
Fully refundable
The price is ฿5,667 per night from 20 Jul to 21 Jul
฿5,667
฿6,948 total
20 Jul - 21 Jul
includes taxes & fees
8.4/10 Very Good! (4,288 reviews)
"For going through some recent renovations the rooms are still aged."

Reviewed on 15 Jul 2025

Holiday Inn Toronto Downtown Centre by IHG
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.

Popular places to visit

What to do in Oakville

Frequently asked questions

How much does an Oakville holiday package cost?
You can pick up a holiday package to this popular destination on Expedia. However, how much your holiday to Oakville costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Oakville?
You can generally find lower prices and greater availability in January, February and March. Take a look at our cheap Oakville holiday packages and you could get some excellent off-season deals.
How many days is enough for Oakville?
To get the most out of your Oakville holiday, we suggest staying for 2 days. Divide your time between discovering Canadian Golf Hall Of Fame, Cameron's Brewing Company and other well-known attractions, on top of exploring neighbourhoods like Sheridan and Clearview. If you've got some time to spare, include a day trip or tour in your Oakville holiday itinerary.
Is it worth booking a holiday package to Oakville?
Oakville has everything you need for a wonderful getaway. Get your Oakville holiday off to a flying start by checking out top attractions like Glen Abbey Golf Course.
How to find the best Oakville package deals?
Bagging a cheap Oakville package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Oakville package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Oakville holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalised Oakville holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Oakville?
If you have your Oakville holiday dates finalized, book early to score some fantastic deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spontaneous trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Oakville?

  1. Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to visit Oakville.
  2. Set your budget: Consider costs like transportation, flights and meals when calculating how much to put aside for your trip to Oakville. Then, select a hotel that fits your budget, whether that's an affordable option or a lavish retreat.
  3. Determine how many days away: Start by listing all the attractions and activities you want to get to in Oakville. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Oakville holiday package.

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