Oakville Vacations

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    Save up to SARĀ 5,400 when you book a flight and hotel together*

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

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Find the Best Oakville Vacation Packages

Oakville Hotel Deals

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 SARĀ 354 per night from Aug 9 to Aug 10
SARĀ 354
SARĀ 407 total
9 Aug - 10 Aug
includes taxes & fees
8.6/10 Excellent! (1,381 reviews)
"The hotel is closed to restaurants and shopping. It is also only about 10 to 15 minutes from Lake Compounce Water park. The room are a decent size but the hotel needs a lot of improvement. The doors were falling apart. Our room smelt like urine. Breakfast was not the greatest. The furniture is old. ..."

Reviewed on 21 July 2026

Holiday Inn Express Southington by IHG
Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

3 out of 5
201 Washington Avenue North Haven CT
Fully refundable
The price is SARĀ 436 per night from Aug 5 to Aug 6
SARĀ 436
SARĀ 501 total
5 Aug - 6 Aug
includes taxes & fees
7.6/10 Good! (1,003 reviews)
"The first floor carpet in the hallway was stained and smelled bad. The second floor was a little better as it appeared to have been replaced recently. We will find other options next time instead of staying in a clarion inn."

Reviewed on 22 July 2026

Clarion Inn North Haven - New Haven North
Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road Southbury CT
Fully refundableReserve now, pay when you stay
The price is SARĀ 348 per night from Aug 19 to Aug 20
SARĀ 348
SARĀ 400 total
19 Aug - 20 Aug
includes taxes & fees
Wyndham Southbury
See all 667 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 can snap up a vacation package to this top destination on Expedia. However, how much your vacation to Oakville costs will depend on the season, length of stay and hotel choice.
What are the cheapest months to go to Oakville?
You're likely to find lower rates and greater availability in January, February and March. Check out our cheap Oakville vacation packages and you could score some great off-season deals.
How to find the best Oakville package deals?
Use Expedia's filters to help you find some unbeatable Oakville package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Oakville package deals in the off-peak season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book an Oakville vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the flexibility to create a customized Oakville vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Oakville?
If you've got your Oakville vacation dates locked in, book early to bag some awesome deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment getaways? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Oakville?

  1. Choose when to go: Check your schedule and get packing. Your favorite time of year and the type of activities on offer will also help you decide when to escape to Oakville.
  2. Calculate your budget: Ensure you have enough money to pay for everything from transportation and food to flights and activities. Your hotel will probably be the largest expense during your trip to Oakville.
  3. Determine how many days away: Start by listing all the attractions you want to experience in Oakville. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, hotels, car rental and more into a customized Oakville vacation package.