Oakville Vacations from $817

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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.

The Latest Oakville vacation packages

Price found within the past 48 hours. Click for updated prices.
New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY

New 3BR Townhouse, Minutes to Niagara Falls and Brock University by GLOBALSTAY

4 out of 5
Save 100% on your flight
Price was $1,209, price is now $817 per person
$817
per person
Jun 18 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9/10 Wonderful! (32 reviews)
Really enjoyed my stay at this townhouse. It’s located in a quiet, peaceful neighborhood, which made it easy to relax. The home itself was clean, comfortable, and had all the amenities I needed for a smooth stay. The backyard was a great bonus. This was a great balance of comfort, convenience, and privacy. I’d definitely stay here again!

Reviewed on Apr 30, 2026

Etobicoke Suites

Etobicoke Suites

3 out of 5
Etobicoke
Price was $1,925, price is now $1,245 per person
$1,245
per person
Jun 22 - Jun 29
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9/10 Wonderful! (29 reviews)
The space was bright and nicely arranged. Made our trip more enjoyable.

Reviewed on Feb 5, 2026

Vine Ridge Resort

Vine Ridge Resort

2.5 out of 5
Price was $1,367, price is now $902 per person
$902
per person
Jul 4 - Jul 11
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
8.6/10 Excellent! (93 reviews)
perfect for family get away! will surely comeback

Reviewed on Nov 12, 2025

Hotel Riu Plaza Toronto

Hotel Riu Plaza Toronto

4 out of 5
Downtown Toronto
Price was $1,218, price is now $831 per person
$831
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Toronto (YYZ)
9.2/10 Wonderful! (3,130 reviews)
Breakfast was nice, the staff were always friendly and the room was really nice. It’s also in a great location

Reviewed on May 13, 2026

1 Hotel Toronto

1 Hotel Toronto

5 out of 5
Downtown Toronto
Price was $2,061, price is now $1,431 per person
$1,431
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Toronto (YYZ)
9.6/10 Exceptional! (712 reviews)
The rooms are beautifully designed. The service is impeccable. Would definitely stay here again.

Reviewed on May 10, 2026

Don't see what you're looking for?
See all available trips from Columbus to Oakville
View all trips

Discover the most popular places to visit in Oakville

Rogers Centre

Rogers Centre

4.5/5(670 reviews)

Come to this multipurpose stadium to watch baseball matches and football games, listen to concerts of famous bands, see family shows or simply tour this central entertainment complex.

Rogers Centre
CN Tower

CN Tower

4.5/5(1,752 reviews)

Take the glass elevator to the lookout points on Toronto’s iconic landmark to enjoy views as far as Niagara Falls or have dinner in high style.

CN Tower
Canada's Wonderland

Canada's Wonderland

4/5(283 reviews)

The highlight at this amusement park is the super-fast Leviathan ride, but there are 15 other roller coasters and more than 200 attractions to explore.

Canada's Wonderland

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 Day Tour from Toronto

Niagara Falls Day Tour from Toronto

$52
per adult
96% of travellers recommend
Niagara Falls Day Tour from Toronto
See all activities in Oakville

Oakville Hotel Deals

Sandman Hotel Oakville

Sandman Hotel Oakville

3.5 out of 5
3451 South Service Road West Oakville ON
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $113 total per night from Jun 13 to Jun 14
$113 total
Jun 13 - Jun 14
Total with taxes and fees
8.8/10 Excellent! (2,267 reviews)
Nice place great room! Friendly staff.

Reviewed on May 12, 2026

Sandman Hotel Oakville
Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W Toronto ON
Fully refundableReserve now, pay when you stay
$133 nightly
The price is $163 total per night from May 18 to May 19
$163 total
May 18 - May 19
Total with taxes and fees
8.4/10 Very Good! (14,887 reviews)
The room was nice and

Reviewed on May 13, 2026

Chelsea Hotel, Toronto
DoubleTree by Hilton Hotel Toronto Downtown

DoubleTree by Hilton Hotel Toronto Downtown

4 out of 5
108 Chestnut St Toronto ON
Fully refundableReserve now, pay when you stay
$160 nightly
The price is $196 total per night from May 17 to May 18
$196 total
May 17 - May 18
Total with taxes and fees
9/10 Wonderful! (5,934 reviews)
Clean room, sheets feel great, staff were very nice and allow us to check out late at no extra cost.

Reviewed on May 13, 2026

DoubleTree by Hilton Hotel Toronto Downtown
See all 4,925 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does an Oakville vacation package cost?
You can pick up a vacation package to this popular destination from $817 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.