Oakville Vacations from $1,007

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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.
Hotel Victoria

Hotel Victoria

3 out of 5
Downtown Toronto
Price was $1,412, price is now $1,007 per person
$1,007
per person
Aug 18 - Aug 22
found 21 hours ago
Roundtrip non-stop flight included
New York (JFK) to Toronto (YYZ)
8.4/10 Very Good! (1,397 reviews)
Location is pretty central.

Reviewed on Jun 12, 2026

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $2,265, price is now $1,269 per person
$1,269
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Toronto (YYZ)
9.2/10 Wonderful! (3,600 reviews)
Service was outstanding

Reviewed on Jun 13, 2026

TOOR Hotel Toronto, part of JdV by Hyatt

TOOR Hotel Toronto, part of JdV by Hyatt

4 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,773, price is now $1,165 per person
$1,165
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Toronto (YYZ)
9.4/10 Exceptional! (750 reviews)
Very well maintained, and close to downtown

Reviewed on Jun 7, 2026

Residence Inn by Marriott Toronto Downtown / Entertainment District

Residence Inn by Marriott Toronto Downtown / Entertainment District

3.5 out of 5
Downtown Toronto
Save 100% on your flight
Price was $1,999, price is now $1,383 per person
$1,383
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Toronto (YYZ)
9.2/10 Wonderful! (3,298 reviews)
Very nice stay! Clean and comfortable room. Staff very friendly and helpful.

Reviewed on Jun 10, 2026

Modern Apartments in North York

Modern Apartments in North York

4 out of 5
North York
Save 100% on your flight
Price was $1,517, price is now $1,070 per person
$1,070
per person
Aug 20 - Aug 23
found 14 hours ago
Roundtrip flight included
Miami (MIA) to Toronto (YYZ)
8.2/10 Very Good! (346 reviews)
check in was a bit delayed due to cleaning. (Our check-in was at 3, we got in a little after 3:30) Apart from that, parking was quite easy to find along with great public transportation and restaurants near by. I would stay here again, very justifiable for the price.

Reviewed on Jun 6, 2026

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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
$157 nightly
The price is $193 total per night from Jun 21 to Jun 22
$193 total
Jun 21 - Jun 22
Total with taxes and fees
8.4/10 Very Good! (15,199 reviews)
"Great hotel with friendly staff. Our daughter loved the pool with slide."

Reviewed on Jun 13, 2026

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
$137 nightly
The price is $168 total per night from Jul 5 to Jul 6
$168 total
Jul 5 - Jul 6
Total with taxes and fees
8.6/10 Excellent! (5,956 reviews)
"Great location, but the bed linens had a very unpleasant odor."

Reviewed on Jun 13, 2026

Holiday Inn Toronto Downtown Centre by IHG
Fairmont Royal York

Fairmont Royal York

4 out of 5
100 Front St West Toronto ON
Fully refundable
$224 nightly
The price is $275 total per night from Jul 5 to Jul 6
$275 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (8,219 reviews)
"We enjoyed our stay for FIFI World Football opening game of Canada vs Bosnia."

Reviewed on Jun 13, 2026

Fairmont Royal York
See all 5,287 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 $1,007 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.