Oakville Holidays

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 Rp173.195 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

Top hotels in Oakville

Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
The price is Rp1.507.138 per night from 27 Jul to 28 Jul
Rp1.507.138
Rp1.733.209 total
27 Jul - 28 Jul
includes taxes & fees
8/10 Very Good! (1,003 reviews)
"No room service on Monday I was not notified about that The Dish tv network I have a problem with every time I stay"

Reviewed on 16 Jul 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 Rp1.645.407 per night from 14 Aug to 15 Aug
Rp1.645.407
Rp1.892.218 total
14 Aug - 15 Aug
includes taxes & fees
7.4/10 Good! (1,022 reviews)
"Good stay no problems at all"

Reviewed on 7 Jul 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 Rp1.905.579 per night from 10 Aug to 11 Aug
Rp1.905.579
Rp2.191.416 total
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (1,032 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 13 Jul 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 holiday 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 holiday to Oakville costs.
What are the cheapest months to go to Oakville?
If you're hoping to snag a cheap Oakville holiday package, consider travelling in January, February and March. You're likely to find better rates on airfares and hotels during these months --- ideal for budget-conscious travellers.
How many days is enough for Oakville?
The ideal duration of your Oakville holiday 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 holiday as a package?
Expedia holiday 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 personalised Oakville holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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 favourite 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 accommodation: After you've settled on your dates and duration, lock in the right Oakville holiday package for you.

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