Oakville Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.

Top Oakville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Peter Street Downtown Toronto Suites

Peter Street Downtown Toronto Suites

4 out of 5
Downtown Toronto
Price was CA $1,009, price is now CA $692 per person
CA $692
per person
Oct 1 - Oct 4
just found
Roundtrip non-stop flight included
Halifax (YHZ) to Toronto (YYZ)
10/10 Exceptional! (1 review)
Great stay! Modern clean condo in a central location

Reviewed on Jul 12, 2026

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was CA $2,209, price is now CA $1,313 per person
CA $1,313
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9.4/10 Exceptional! (3,874 reviews)

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Price was CA $3,369, price is now CA $2,032 per person
CA $2,032
per person
Aug 29 - Sep 3
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9.6/10 Exceptional! (762 reviews)
Absolutely stunning hotel. Amazing rooftop pool. Delicious restaurants and cocktail bar. Perfect choice for a girlfriend’s getaway.

Reviewed on Jul 18, 2026

Modern Lillian Street Condos Midtown Toronto

Modern Lillian Street Condos Midtown Toronto

4 out of 5
Old Toronto
Price was CA $1,495, price is now CA $997 per person
CA $997
per person
Sep 23 - Sep 28
found 1 day ago
Roundtrip flight included
Halifax (YHZ) 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

Shangri-La Toronto

Shangri-La Toronto

5 out of 5
Downtown Toronto
Price was CA $3,408, price is now CA $2,320 per person
CA $2,320
per person
Sep 18 - Sep 23
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9.6/10 Exceptional! (1,303 reviews)

Ready to book your vacation to Oakville?

 

Choose your dates

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
The price is CA $199 per night from Jul 26 to Jul 27
CA $199
CA $244 total
Jul 26 - Jul 27
includes taxes & fees
9/10 Wonderful! (609 reviews)
"Very good hotel"

Reviewed on Jul 18, 2026

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
The price is CA $258 per night from Jul 26 to Jul 27
CA $258
CA $317 total
Jul 26 - Jul 27
includes taxes & 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
The price is CA $204 per night from Jul 26 to Jul 27
CA $204
CA $251 total
Jul 26 - Jul 27
includes taxes & fees
8.6/10 Excellent! (6,151 reviews)
"위치 좋고 조식도 좋습니다. 다음에 또 머물가치가 있어요"

Reviewed on Jul 18, 2026

Holiday Inn Toronto Downtown Centre by IHG
See all 5,478 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Oakville attractions

Coronation Park

8.4/10 (114 reviews)
Commune with nature and explore the great outdoors at Coronation Park during your travels in Oakville. Stroll along the lakeside in this family-friendly area, or check out its top-notch restaurants.
See properties

What to do in Oakville

Toronto: Ripley's Aquarium of Canada Entry Ticket

Toronto: Ripley's Aquarium of Canada Entry Ticket

CA $46
per adult
94% of travellers recommend
Toronto: Ripley's Aquarium of Canada Entry Ticket
Toronto: Casa Loma Entry Ticket

Toronto: Casa Loma Entry Ticket

CA $45
per adult
90% of travellers recommend
Toronto: Casa Loma Entry Ticket
Art Gallery of Ontario: General Admission

Art Gallery of Ontario: General Admission

CA $30
per adult
90% of travellers recommend
Art Gallery of Ontario: General Admission
See all activities in Oakville

Frequently asked questions

How much does an Oakville vacation package cost?
You'll find cheap prices from CA $692 on Expedia for your Oakville getaway. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Oakville costs.
What are the cheapest months to go to Oakville?
If you're looking to snag a cheap Oakville vacation package, consider visiting in January, February and March. You'll usually find lower prices on hotels and flights during these months — perfect for budget-conscious travellers.
How many days is enough for Oakville?
To get the most out of an Oakville vacation, we suggest staying for 2 days. Split your time between visiting Erindale Park, iFLY Toronto Oakville and other top attractions, on top of exploring neighbourhoods like Sheridan and Clearview. If you've got some spare time, add a tour or day trip to your Oakville vacation itinerary.
Is it worth booking a vacation package to Oakville?
Oakville is a good vacation destination with attractions like Glen Abbey Golf Course among the many things to keep you entertained. Whether you're travelling with the family or planning a trip with friends, an Oakville vacation promises a good time for everyone.
How to find the best Oakville package deals?
Bagging a cheap Oakville package deal is a cinch with Expedia. After you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a few filters and see 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 discover the most wallet-friendly Oakville package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book an Oakville vacation as a package?
An Expedia vacation package could land you great savings when compared to arranging flights and stays separately. Better still, you can customize your Oakville trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Oakville?
If you have your Oakville travel dates finalized, book as soon as you can to bag some incredible deals. With Expedia, you can generally reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Oakville?

  1. Choose when to go: Check your calendar and pack your bags. Your favourite time of year and the available activities will also help you decide when to escape to Oakville.
  2. Work out your budget: Ensure you have enough money to cover everything from meals and transportation to activities and flights. Your hotel will probably be the largest expense during your trip to Oakville.
  3. Decide your trip length: Consider how much time you want to spend exploring Oakville. Plan your days so you can get to all the activities and attractions you're interested in without rushing.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Oakville vacation package.

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.