Oakville Vacations from $761

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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.
Modern Lillian Street Condos Midtown Toronto

Modern Lillian Street Condos Midtown Toronto

4 out of 5
Old Toronto
Price was $1,074, price is now $761 per person
$761
per person
Sep 23 - Sep 28
found 14 hours ago
Roundtrip flight included
New York (NYC) to Toronto (YYZ)
8.4/10 Very Good! (301 reviews)
The confirmation process was complicated by the fact that several steps were required to finalize the contract. The room we got was not what I believed I requested but GlobalStay, the management firm would not provide any proof that I had mistakenly ordered the wrong room. Nor would they offer any option to correct the issue. The parking space that we were told to use was occupied by another vehicle. As requested by GlobalStay I provided photo evidence and a photo of where I ended up parking so GlobalStay could inform building management. They did not do so. Consequently my vehicle was ticketed for $150 dollars in fines. I would avoid GlobalStay if possible.

Reviewed on Jul 12, 2026

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Price was $2,182, price is now $1,321 per person
$1,321
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (762 reviews)

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was $1,432, price is now $890 per person
$890
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.4/10 Exceptional! (3,874 reviews)
Siempre por lo menos un ascensor dañado . Muy buen desayuno . Trato amable

Reviewed on Jul 17, 2026

Four Seasons Hotel Toronto

Four Seasons Hotel Toronto

5 out of 5
Old Toronto
Price was $1,933, price is now $1,279 per person
$1,279
per person
Sep 10 - Sep 13
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (978 reviews)
Great location, very friendly and helpful staff. Hotel is brand new and amenities are top notch.

Reviewed on Jul 17, 2026

Shangri-La Toronto

Shangri-La Toronto

5 out of 5
Downtown Toronto
Price was $2,041, price is now $1,425 per person
$1,425
per person
Sep 25 - Sep 29
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (1,287 reviews)

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Stay near popular Oakville attractions

Coronation Park

8.4/10 (114 reviews)
Coronation Park offers a serene lakefront escape with expansive green spaces and mature trees along Lake Ontario. Families can enjoy the accessible playground, splash pad, and picnic areas with waterfront views.
See properties

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)

$140
per adult
84% of travellers recommend
Niagara Falls Day & Night Tour - Cruise & Dinner (Optional)
Toronto: Casa Loma Entry Ticket

Toronto: Casa Loma Entry Ticket

$32
per adult
90% of travellers recommend
Toronto: Casa Loma Entry Ticket
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
$145 nightly
The price is $177 total per night from Jul 26 to Jul 27
$177 total
Jul 26 - Jul 27
Total with taxes and fees
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
$184 nightly
The price is $226 total per night from Jul 26 to Jul 27
$226 total
Jul 26 - Jul 27
Total with taxes and fees
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
$162 nightly
The price is $199 total per night from Jul 26 to Jul 27
$199 total
Jul 26 - Jul 27
Total with taxes and fees
8.6/10 Excellent! (6,144 reviews)
"Excellent staff. Breakfast was overpriced"

Reviewed on Jul 17, 2026

Holiday Inn Toronto Downtown Centre by IHG
See all 5,465 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 $761 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.