Oakville Vacations from $695

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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.
Burano Condos in Downtown Toronto

Burano Condos in Downtown Toronto

3 out of 5
Downtown Toronto
Price was $970, price is now $695 per person
$695
per person
Aug 6 - Aug 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Toronto (YYZ)
8.6/10 Excellent! (289 reviews)
excellent location - can walk to amenities / food places / transportation

Reviewed on Jun 10, 2026

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Price was $1,992, price is now $1,300 per person
$1,300
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Toronto (YYZ)
9.6/10 Exceptional! (748 reviews)
I was concerned when I arrived because I was in the heart of downtown during the World Cup, and this clearly was a bustling location. The clientele all appeared well-heeled and ready for a good time. I personally prefer a low key quiet stay, and I expressed that desire to the staff. They reserved me a beautiful room on a higher floor. I told them that I am partial to quite few pillows and found a veritable pillow fort waiting for me! I had asked for a steamer to prepare a dress for an event I was attending and one was brought to me almost immediately. The staff were incredibly warm and welcoming. The hotel itself if beautiful. Truly the only constructive feedback I could give was that there was no jam with my croissant, and no English Breakfast tea in my room. Both entirely non-issues. I will absolutely be staying here again.

Reviewed on Jun 17, 2026

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was $1,137, price is now $779 per person
$779
per person
Aug 6 - Aug 9
found 19 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Toronto (YYZ)
9.2/10 Wonderful! (3,715 reviews)
Breakfast is a must get in this hotel. . It's really good. You will be satisfied. Staff is great and make you feel comfortable. The hotel doesn't have its own parking but there is a couple of places near where you can park.

Reviewed on Jun 27, 2026

One King West Hotel & Residence

One King West Hotel & Residence

4 out of 5
Downtown Toronto
Price was $1,256, price is now $886 per person
$886
per person
Jul 31 - Aug 4
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Toronto (YYZ)
9.4/10 Exceptional! (7,991 reviews)
I would easily give this hotel five stars, except for one recurring issue. Leaving dirty laundry bins in the hallway next to the elevators 24/7 was an eyesore and felt quite distasteful. Aside from that, everything else was fantastic. The food was great, the service was marvelous, the fellow guests were wonderful, and I truly enjoyed the atmosphere and location.

Reviewed on Jun 26, 2026

Elegant Downtown Apartments

Elegant Downtown Apartments

4 out of 5
Downtown Toronto
Price was $1,048, price is now $739 per person
$739
per person
Aug 6 - Aug 10
found 4 hours ago
Roundtrip non-stop flight included
Chicago (CHI) to Toronto (YYZ)
8/10 Very Good! (669 reviews)
Communication is a big issue. The listed number did not have voicemail capability. Staff are not local most likely overseas best time to call and get response is between 6 am - 10 am EST. Dryer was not functioning during entire stay. Customer support indicated local support would be contacted. Never heard from anyone. Do not expect to watch anything other than Netflix during stay. Hulu was not available as advertised and local channels not available. Great location, adequately clean. Deposit refunded within 2 days

Reviewed on Jun 24, 2026

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Stay near popular Oakville attractions

Coronation Park

8.4/5 (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: Casa Loma Entry Ticket

Toronto: Casa Loma Entry Ticket

$33
per adult
90% of travellers recommend
Toronto: Casa Loma Entry Ticket
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)

$144
per adult
86% of travellers recommend
Niagara Falls Day & Night Tour - Cruise & Dinner (Optional)
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
$149 nightly
The price is $183 total per night from Jul 5 to Jul 6
$183 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (242 reviews)
"Great hotel in downtown Toronto!"

Reviewed on Jun 27, 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
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $169 total per night from Jul 6 to Jul 7
$169 total
Jul 6 - Jul 7
Total with taxes and fees
8.6/10 Excellent! (5,988 reviews)
"Pleasant and courteous staff as usual."

Reviewed on Jun 26, 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 refundableReserve now, pay when you stay
$182 nightly
The price is $223 total per night from Jun 28 to Jun 29
$223 total
Jun 28 - Jun 29
Total with taxes and fees
9/10 Wonderful! (8,263 reviews)
"Everything was wonderful"

Reviewed on Jun 27, 2026

Fairmont Royal York
See all 5,374 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 $695 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.

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