Oakville Vacations from $650

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Your Oakville Vacation

With everything organized before you set off, our Oakville vacation packages let you simply focus on vacationing! One place to base yourself in this captivating city is Port Credit, which is great for watersports and walking. Fill up your itinerary with tours of University of Toronto Mississauga, Sheridan College and Bronte Creek Provincial Park, some of the things you shouldn't miss during a trip to Oakville. Don't delay visiting this destination any longer. The ultimate Oakville vacation is only a few clicks away with Expedia.

The Latest Oakville vacation packages

Price found within the past 48 hours. Click for updated prices.
Sterling Inn & Spa - an Ontario's Finest Inn

Sterling Inn & Spa - an Ontario's Finest Inn

4 out of 5
Clifton Hill
Save 100% on your flight
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
New York (JFK) to Toronto (YYZ)
9.6/10 Exceptional! (1,896 reviews)
One of the best hotels in the Niagara area. Everything about this property was spot on. Very clean, spacious rooms and convenient parking at a reasonable price. The only hotel I will stay at from now on. Excellent!

Reviewed on Jul 14, 2025

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
per person
Sep 18 - Sep 21
found 1 day ago
Roundtrip flight included
New York (JFK) to Toronto (YYZ)
9.4/10 Exceptional! (541 reviews)
Wonderful hotel. Great people. Clean modern rooms. Amazing restaurant. We will return.

Reviewed on Jul 12, 2025

GLOBALSTAY. Elegant Downtown Apartments

GLOBALSTAY. Elegant Downtown Apartments

4 out of 5
Downtown Toronto
Save 100% on your flight
per person
Sep 16 - Sep 23
found 1 day ago
Roundtrip flight included
New York (NYC) to Toronto (YYZ)
7.2/10 Good! (340 reviews)
We very much enjoyed our stay, it worked perfectly for us!

Reviewed on Jul 8, 2025

Newmarket Hotel & Suites

Newmarket Hotel & Suites

2.5 out of 5
Save 100% on your flight
per person
Aug 26 - Sep 2
found 20 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
8/10 Very Good! (1,000 reviews)
Met all my expectations

Reviewed on Jul 8, 2025

Woodbourne Inn

Woodbourne Inn

4 out of 5
St. Davids
Save 100% on your flight
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Toronto (YYZ)
9.8/10 Exceptional! (483 reviews)
I enjoyed the personal touches, ambience the friendliness of staff and the opportunity to select pre breakfast items each morning. The location was quiet and close to shops and short drive to the lake. I would love to visit again soon! Thank you to staff and our wonderful chefs for an excellent weekend.

Reviewed on Jun 16, 2025

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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
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Bronte

1 out of top 10 points of interest in this area
4/5(14 area reviews)

While visiting Bronte, you might make a stop by sights like Lake Ontario and Bronte Harbour.

Find hotels in Bronte

Discover the most popular places to visit in Oakville

Rogers Centre which includes signage and a city

Rogers Centre

4.5/5(661 reviews)

Come to this multipurpose stadium to watch baseball matches and football games, listen to concerts of famous bands, see family shows or simply tour this central entertainment complex.

Rogers Centre
CN Tower showing skyline, a city and modern architecture

CN Tower

4.5/5(1,736 reviews)

Take the glass elevator to the lookout points on Toronto’s iconic landmark to enjoy views as far as Niagara Falls or have dinner in high style.

CN Tower
CN Tower which includes rides

Canada's Wonderland

4/5(280 reviews)

The highlight at this amusement park is the super-fast Leviathan ride, but there are 15 other roller coasters and more than 200 attractions to explore.

Canada's Wonderland

What to do in Oakville

Horseshoe Falls

Niagara Falls Day Tour from Toronto

$69
per adult
96% of travellers recommend
Niagara Falls Day Tour from Toronto
Niagara Falls Evening Tour with Boat, Dinner & Illumination Tower

Niagara Falls Evening Tour with Boat, Dinner & Illumination Tower

$87
per adult
90% of travellers recommend
Niagara Falls Evening Tour with Boat, Dinner & Illumination Tower
Niagara Falls Day Tour from Toronto with Buffet Lunch

Niagara Falls all inclusive tour with skip-the-line boat and lunch

$124
per adult
84% of travellers recommend
Niagara Falls all inclusive tour with skip-the-line boat and lunch
See all activities in Oakville

Oakville Hotel Deals

Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W, Toronto, ON
Fully refundableReserve now, pay when you stay
$154 nightly
The price is $189 total per night from Aug 4 to Aug 5
$189 total
Aug 4 - Aug 5
Total includes taxes and fees
8.2/10 Very Good! (11,632 reviews)
"Nice stayed"

Reviewed on Jul 14, 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
$269 nightly
The price is $329 total per night from Aug 4 to Aug 5
$329 total
Aug 4 - Aug 5
Total includes taxes and fees
8.8/10 Excellent! (6,842 reviews)
"Stayed here while attending a concert nearby, such a beautiful hotel!"

Reviewed on Jul 13, 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
$180 nightly
The price is $221 total per night from Jul 20 to Jul 21
$221 total
Jul 20 - Jul 21
Total includes taxes and fees
8.4/10 Very Good! (4,284 reviews)
"Older hotel. Rooms are smaller. But the buffet option is affordable and the hotel is very close to the subway."

Reviewed on Jul 15, 2025

Holiday Inn Toronto Downtown Centre by IHG
See all 4,399 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.

Find the Best Oakville Vacation Packages

Oakville Essential Information

Language
English
Currency
Canadian dollars
Closest Airport
Pearson Intl. Airport (YYZ)
Population
165,700
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Living Arts Centre, Oakville Centre for the Performing Arts and Playdium

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Frequently asked questions

How much does an Oakville vacation package cost?
You can pick up a vacation package to this popular destination from $650 on Expedia. However, how much your vacation 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 usually find reduced prices and better availability in December, January and February. Take a look at our cheap Oakville vacation packages and you could get some great off-season discounts.
How many days is enough for Oakville?
To fully enjoy an Oakville vacation, we suggest staying for 2 days. Split your time between visiting Canadian Golf Hall Of Fame, Cameron's Brewing Company and other major sights, on top of experiencing neighborhoods like Clearview and Bronte. If you've got some spare time, include a day trip or tour in your Oakville vacation itinerary.
Is it worth booking a vacation package to Oakville?
Oakville offers everything you need for an amazing getaway. Begin your Oakville vacation on a high note by exploring popular 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 vacation as a package?
Expedia vacation 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 personalized Oakville vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Oakville?
If you have your Oakville vacation 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 diary and get your bags packed. Your preferred season and the activities available will also help you decide when to visit Oakville.
  2. Budget wisely: In addition to the cost of your hotel, you should consider other expenses. These include transportation, food and flights. Also, put aside a little extra for unexpected costs that may come up during your trip to Oakville.
  3. Organize your Oakville getaway with our trip planning tool: Search for and book stays and activities all in one place. You can also collaborate with your group to plan an unforgettable trip to Oakville together.
  4. Determine how many days away: Start by compiling a list of the attractions and activities you'd like to get to in Oakville. Then, estimate how long you'll need at each, as well as any travel time.
  5. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalized Oakville vacation package.
  6. Book experiences or activities in advance: Whether it's a ticket to a big attraction or a day trip, you won't have to worry about missing out on Oakville's highlights. Find all the exciting things to do in Oakville in Oakville with our dedicated travel guide.

Does Expedia offer Book Now, Pay Later Oakville vacation packages?
If you're like us, you love discovering new places but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can break down the overall cost of your Oakville break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.