Oakville Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Plan, book, travel with confidence

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    Better together

    Save up to ₩234,741 when you book a flight and hotel together*
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    Find the right fit

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

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

Find the Best Oakville Vacation Packages

Oakville Hotel Deals

Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is ₩128,603 per night from Jul 27 to Jul 28
₩128,603
₩147,893 total
Jul 27 - Jul 28
includes taxes & fees
8/10 Very Good! (1,017 reviews)
"The only thing I didn’t care for was the handicap rooms are way at the end of the hallway hard to get to the rooms"

Reviewed on Jul 14, 2025

Wyndham Southbury
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is ₩140,401 per night from Aug 13 to Aug 14
₩140,401
₩161,462 total
Aug 13 - Aug 14
includes taxes & fees
7.4/10 Good! (1,025 reviews)
"Q"

Reviewed on Jul 15, 2025

Clarion Inn
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
120 Laning St, Southington, CT
Fully refundable
The price is ₩162,402 per night from Aug 10 to Aug 11
₩162,402
₩186,762 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (1,034 reviews)
"Very nice staff, I was able to check in early and it was a quick process. I got to switch rooms (didn’t need two beds) with no problem at all."

Reviewed on Jul 13, 2025

Holiday Inn Express Southington by IHG
See all 594 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.

Frequently asked questions

How much does an Oakville vacation package cost?
You'll find cheap prices on Expedia for your Oakville break. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Oakville costs.
What are the cheapest months to go to Oakville?
If you're hoping to snag a cheap Oakville vacation package, consider traveling in January, February and March. You're likely to find better rates on airfares and hotels during these months --- ideal for budget-conscious travelers.
How many days is enough for Oakville?
The ideal duration of your Oakville vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to check out all the leading sights and discover some hidden spots along the way.
How to find the best Oakville package deals?
Start your search for an Oakville package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply a few filters, like "Popular locations" and "Property type," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Oakville package deal straight away, simply change your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Oakville escape off to a flying start.
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 hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically score 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 airline, accommodation type and car class.
When to book a vacation package to Oakville?
If you have your Oakville travel dates locked in, book as soon as you can to grab some incredible deals. With Expedia, you can often 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 your travel dates: What you plan to do in Oakville and your favorite season can help you decide when to travel.
  2. Set your budget: Factor in expenses like transportation, flights and meals when calculating how much to save for your trip to Oakville. Then, choose a property that fits your budget, whether that's a wallet-friendly option or a deluxe getaway.
  3. 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 for each, including any travel time.
  4. Bundle your airfare and accommodations: After you've settled on your dates and duration, lock in the right Oakville vacation package for you.

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