Oakville Trips (flight + hotel)

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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 P5,288 per night from Aug 24 to Aug 25
P5,288
P6,081 total
Aug 24 - Aug 25
includes taxes & fees
8/10 Very Good! (1,004 reviews)
Thumbs up
"Nice hotel, would stay again. Bartender Anthony was great."

Reviewed on Aug 13, 2025

Wyndham Southbury
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 P6,336 per night from Aug 31 to Sep 1
P6,336
P7,286 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,065 reviews)
"It was walking distance to Thompson’s point where the music festival I went to see was being held. The staff from the front desk to cleaning staff, were all very friendly. More hooks and/or towel bars in the bathroom. Other than the shelf/rack that all the towels were stored on that is IN THE SHOWER ..."

Reviewed on Aug 15, 2025

Holiday Inn Express Southington by IHG
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is P5,822 per night from Sep 14 to Sep 15
P5,822
P6,695 total
Sep 14 - Sep 15
includes taxes & fees
7.4/10 Good! (1,001 reviews)
"Staff are"

Reviewed on Aug 13, 2025

Clarion Inn
See all 608 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.