Oakville Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top hotels in Oakville
Holiday Inn Express Southington by IHG
120 Laning St Southington CT
Fully refundableReserve now, pay when you stay
S$135
16 Aug - 17 Aug
includes taxes & fees
8.6/10 Excellent! (1,416 reviews)
"It was ok a little dated breakfast was pretty good coffee was excellent ..."
Reviewed on 11 Aug, 2026
Wyndham Southbury
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
S$140
6 Sept - 7 Sept
includes taxes & fees
8.2/10 Very good! (1,273 reviews)
"We were hungry and there wasn’t any restaurants off the exit, but fortunately for us Wyndham had a restaurant. The service was friendly and fast and the food was delicious!"
Reviewed on 11 Aug, 2026
Courtyard by Marriott Waterbury Downtown
63 Grand St Waterbury CT
Fully refundableReserve now, pay when you stay
S$111
30 Aug - 31 Aug
includes taxes & fees
8.4/10 Very good! (1,270 reviews)
"Only dislike is payed parking otherwise very clean and comfortable!!!"
Reviewed on 11 Aug, 2026
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?
- Choose your travel dates: What you plan to do in Oakville and your favourite season can help you decide when to travel.
- 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.
- 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.
- 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
