Oakville Vacation Packages

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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.

Top Oakville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cozy Family Retreat Minutes From Falls

Cozy Family Retreat Minutes From Falls

3 out of 5
Hennepin
Price was CA $1,151, price is now CA $811 per person
CA $811
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Winnipeg (YWG) to Toronto (YYZ)
No reviews

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Price was CA $5,765, price is now CA $3,683 per person
CA $3,683
per person
Oct 20 - Oct 27
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Toronto (YYZ)
9.6/10 Exceptional! (773 reviews)

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was CA $1,582, price is now CA $1,033 per person
CA $1,033
per person
Oct 11 - Oct 15
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Toronto (YYZ)
9.4/10 Exceptional! (4,215 reviews)
This was a great hotel. Beautiful clean and great staff. Central location to every ring in Toronto. Great buffet breakfast I visited everyday. Can’t wait to stay again soo .

Reviewed on Aug 5, 2026

Kent Motel Niagara on the Lake

Kent Motel Niagara on the Lake

2.5 out of 5
Queenston
Price was CA $1,821, price is now CA $1,274 per person
CA $1,274
per person
Sep 6 - Sep 13
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Toronto (YYZ)
9.6/10 Exceptional! (342 reviews)
Room is very nice parking was easy staff very pleasant. I missed no on site restaurant.

Reviewed on Aug 4, 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
The price is CA $229 per night from Aug 30 to Aug 31
CA $229
CA $274 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (952 reviews)
"The location was great for my hospital visit. Also very close to the Eaton Center. Room was clean; mattress was comfortable."

Reviewed on Aug 5, 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 $314 per night from Aug 30 to Aug 31
CA $314
CA $376 total
Aug 30 - Aug 31
includes taxes & fees
9/10 Wonderful! (8,466 reviews)
"Was awesome"

Reviewed on Aug 5, 2026

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
The price is CA $269 per night from Aug 31 to Sep 1
CA $269
CA $322 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (6,290 reviews)
"Room was cramped, no microwave, poor tv choices"

Reviewed on Aug 4, 2026

Holiday Inn Toronto Downtown Centre by IHG
See all 5,505 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
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Family Vacations
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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
Toronto: Niagara Falls Tour with Boat Cruise and/or Journey

Toronto: Niagara Falls Day Tour + Boat & Behind Falls Entry

CA $87
per adult
98% of travellers recommend
Toronto: Niagara Falls Day Tour + Boat & Behind Falls Entry
See all activities in Oakville

Frequently asked questions

How much does an Oakville vacation package cost?
You'll find cheap prices from CA $811 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.