Oakville Holidays

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Top Flight + Hotel Deals in Oakville

Price found within the past 48 hours. Click for updated prices.
Novotel Toronto Centre
Park Hyatt Toronto
1 Hotel Toronto
Hotel Victoria
GLOBALSTAY. Maple Leaf Square

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 €129 per night from 17 Feb to 18 Feb
€129
includes taxes & fees
17 Feb - 18 Feb
8/10 Very Good! (10,475 reviews)
"I was amazed at the children's check in with stairs to go counter so the child feels important. Hotel is very clean. Amazing and very helpful staff. It was a little confusing with the blue, green and red elevators. But after we overcame the confusion, it was easy after thdt.. Just need room number ..."

Reviewed on 14 Feb 2025

Chelsea Hotel, Toronto
One King West Hotel & Residence
One King West Hotel & Residence
4 out of 5
1 King Street West, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is €118 per night from 9 Mar to 10 Mar
€118
includes taxes & fees
9 Mar - 10 Mar
9/10 Wonderful! (9,427 reviews)
"The room smelled like BO"

Reviewed on 13 Feb 2025

One King West Hotel & Residence
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 €217 per night from 10 Mar to 11 Mar
€217
includes taxes & fees
10 Mar - 11 Mar
8.8/10 Excellent! (6,220 reviews)
"Always a great stay. Never disappointed."

Reviewed on 15 Feb 2025

Fairmont Royal York
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 an Oakville holiday package cost?
You can pick up a holiday package to this popular destination from €885 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.

Popular places to visit

What to do in Oakville

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