Oakville Holidays

Book a Hotel + Flight or Car together to unlock savings

Where to stay in Oakville

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

1 out of top 10 points of interest in this area

If you're spending some time in Bronte, Lake Ontario and Bronte Harbour are top sights worth seeing.

Find hotels in Bronte

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 3.708.237 ₫ per night from 1 Sept to 2 Sept
3.708.237 ₫
4.546.483 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (12,099 reviews)
"Fancy"

Reviewed on 19 Aug 2025

Chelsea Hotel, Toronto
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 3.867.311 ₫ per night from 1 Sept to 2 Sept
3.867.311 ₫
4.741.552 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (4,455 reviews)
"Didn’t like the rooms beside us opening and slamming their doors all night with the security latch pulled across so their doors didn’t actually close. They were coming and going all night. And could hear a lot of street noise."

Reviewed on 18 Aug 2025

Holiday Inn Toronto Downtown Centre by IHG
DoubleTree by Hilton Hotel Toronto Downtown

DoubleTree by Hilton Hotel Toronto Downtown

4 out of 5
108 Chestnut St, Toronto, ON
The price is 4.478.955 ₫ per night from 28 Aug to 29 Aug
4.478.955 ₫
5.491.425 ₫ total
28 Aug - 29 Aug
includes taxes & fees
8.8/10 Excellent! (5,066 reviews)
"Great location . Clean hotel and helpful staff. Updated rooms"

Reviewed on 18 Aug 2025

DoubleTree by Hilton Hotel Toronto Downtown
See all 4,366 properties in Oakville
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

Rogers Centre

Rogers Centre

Catch an event at Rogers Centre during your trip to Toronto. Experience the acclaimed art galleries and entertainment choices in this vibrant area.

Rogers Centre
CN Tower featuring modern architecture, a city and a high-rise building

CN Tower

Find out about the history of CN Tower, a well-known monument in Toronto. Discover the entertainment choices and shops in this vibrant area.

CN Tower
Canada's Wonderland

Canada's Wonderland

Have a fun-filled day at Canada's Wonderland and see why this is a favourite theme park in Vaughan. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

Canada's Wonderland

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.