Oakville Holidays

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Top hotels in Oakville

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 Rp1.869.141 per night from 20 Nov to 21 Nov
Rp1.869.141
Rp2.149.512 total
20 Nov - 21 Nov
includes taxes & fees
8.6/10 Excellent! (1,461 reviews)
"Overall the stay was ok. What bothered us was there were people chatting loud either outside in the parking lot or a floor below us until 11:20PM, that made my son not sleeping well for his early morning game."

Reviewed on 31 Oct 2026

Holiday Inn Express Southington by IHG
Heritage Hotel, Golf & Conference Center

Heritage Hotel, Golf & Conference Center

3.5 out of 5
522 Heritage Road Southbury CT
Fully refundableReserve now, pay when you stay
The price is Rp1.946.810 per night from 18 Nov to 19 Nov
Rp1.946.810
Rp2.551.868 total
18 Nov - 19 Nov
includes taxes & fees
Heritage Hotel, Golf & Conference Center
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St Waterbury CT
Fully refundableReserve now, pay when you stay
The price is Rp1.615.083 per night from 2 Nov to 3 Nov
Rp1.615.083
Rp1.857.345 total
2 Nov - 3 Nov
includes taxes & fees
8.6/10 Excellent! (1,290 reviews)
"Everything was great! Would recommend this Hotel to family."

Reviewed on 30 Oct 2026

Courtyard by Marriott Waterbury Downtown
See all 681 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.