Oakville Vacations from $596

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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.
The Laundry Rooms Station Park Kitchener

The Laundry Rooms Station Park Kitchener

2 out of 5
K-W Hospital
Save 100% on your flight
Price was $846, price is now $596 per person
$596
per person
Mar 31 - Apr 6
found 1 day ago
Roundtrip flight included
New York (LGA) to Toronto (YYZ)
9.2/10 Wonderful! (367 reviews)
Very clean spacious space.

Reviewed on Jan 19, 2026

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,992, price is now $1,229 per person
$1,229
per person
Mar 2 - Mar 5
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Toronto (YYZ)
9.4/10 Exceptional! (632 reviews)
Everything about this hotel exceeded my expectations!

Reviewed on Jan 26, 2026

151 Dan Leckie Way

151 Dan Leckie Way

2.5 out of 5
Downtown Toronto
Price was $1,171, price is now $798 per person
$798
per person
Mar 18 - Mar 21
found 1 day ago
Roundtrip flight included
New York (JFK) to Toronto (YYZ)
9.2/10 Wonderful! (278 reviews)
Everything was great, very clean, with good access and plenty of security in the area. Good underground parking and places to eat right in front of the complex.

Reviewed on Jan 15, 2026

The Laundry Rooms Gaslight Cambridge

The Laundry Rooms Gaslight Cambridge

3 out of 5
Save 100% on your flight
Price was $873, price is now $623 per person
$623
per person
Mar 31 - Apr 6
found 1 day ago
Roundtrip flight included
New York (LGA) to Toronto (YYZ)
9.6/10 Exceptional! (454 reviews)
Room was spotless and relaxing, main desk staff were so helpful and friendly!

Reviewed on Jan 26, 2026

GLOBALSTAY Luxury Townhouse Minutes Away From Waterfront

GLOBALSTAY Luxury Townhouse Minutes Away From Waterfront

3 out of 5
Etobicoke
Price was $1,161, price is now $839 per person
$839
per person
Apr 1 - Apr 7
found 1 day ago
Roundtrip flight included
New York (LGA) to Toronto (YYZ)
8.4/10 Very Good! (9 reviews)
Easy check-in and a pleasant stay.

Reviewed on Jan 27, 2026

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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

Toronto: Ripley's Aquarium of Canada Entry Ticket

Toronto: Ripley's Aquarium of Canada Entry Ticket

$33
per adult
94% of travellers recommend
Toronto: Ripley's Aquarium of Canada Entry Ticket
Niagara Falls lit up at night with firework show nearby

Niagara Falls Day & Night Tour - Cruise & Dinner (Optional)

$136
per adult
86% of travellers recommend
Niagara Falls Day & Night Tour - Cruise & Dinner (Optional)
The highlight of any visit to the Hockey Hall of Fame is the Esso Great Hall, where guests can get close up to hockey's greatest treasure, the Stanley Cup.

Hockey Hall of Fame Admission Ticket

$18
per adult
90% of travellers recommend
Hockey Hall of Fame Admission Ticket
See all activities in Oakville

Oakville Hotel Deals

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
$121 nightly
The price is $148 total per night from Feb 22 to Feb 23
$148 total
Feb 22 - Feb 23
Total with taxes and fees
8.4/10 Very Good! (5,310 reviews)
Staff was lovely

Reviewed on Jan 27, 2026

Holiday Inn Toronto Downtown Centre by IHG
Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
30 Widmer St Toronto ON
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $167 total per night from Feb 7 to Feb 8
$167 total
Feb 7 - Feb 8
Total with taxes and fees
9.2/10 Wonderful! (1,464 reviews)
The location was perfect and it was nice to have breakfast available!

Reviewed on Jan 22, 2026

Hotel Riu Plaza Toronto
Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W Toronto ON
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $183 total per night from Feb 7 to Feb 8
$183 total
Feb 7 - Feb 8
Total with taxes and fees
8.4/10 Very Good! (13,891 reviews)
Spotless rooms and very clean bathrooms.

Reviewed on Jan 26, 2026

Chelsea Hotel, Toronto
See all 4,881 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 $596 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.

Explore a world of travel with Expedia

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