Oakville Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Your Oakville Vacation

Say goodbye to planning hassles and hello to a Oakville vacation package. With the finer details organized before you go, you can focus on discovering every inch of this city, starting with Washington, which is great for nature, history and views. Any trip to Oakville has to include some sightseeing. Black Rock State Park is a superb place to begin exploring. A couple of clicks is all it takes to craft the ideal Oakville vacation on Expedia.

Top Oakville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Super 8 by Wyndham Old Saybrook

Super 8 by Wyndham Old Saybrook

2 out of 5
Price was CA $595, price is now CA $555 per person
CA $555
per person
Aug 9 - Aug 12
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
7/10 Good! (929 reviews)
Good area and served purpose for the price. Rooms could use some cosmetic updates.

Reviewed on Jul 6, 2026

Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $717, price is now CA $619 per person
CA $619
per person
Aug 9 - Aug 12
found 14 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8/10 Very good! (1,001 reviews)
Lage room, Clean and comfortable bed. Bathroom could use updating and an elevated toilet seat. Staff very nice. Would stay again.

Reviewed on Jul 7, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,037, price is now CA $1,873 per person
CA $1,873
per person
Aug 6 - Aug 9
found 11 hours ago
Roundtrip flight included
Montreal (YUL) to New Haven (HVN)
No reviews

Clarion Inn North Haven - New Haven North

Clarion Inn North Haven - New Haven North

3 out of 5
Price was CA $1,012, price is now CA $963 per person
CA $963
per person
Aug 14 - Aug 17
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
7.6/10 Good! (1,010 reviews)
The property is in the middle of upgrading...but it's quiet and location was perfect for me

Reviewed on Jul 5, 2026

Hamden Hotel and Suites – Hamden New Haven

Hamden Hotel and Suites – Hamden New Haven

2.5 out of 5
Price was CA $942, price is now CA $911 per person
CA $911
per person
Aug 14 - Aug 17
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
6.8/10 (1,010 reviews)
I had booked a queen bed room at a lower price. I was given a king bed at much higher price

Reviewed on Jul 4, 2026

Ready to book your vacation to Oakville?

 

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Oakville Hotel Deals

The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave Farmington CT
Fully refundableReserve now, pay when you stay
The price is CA $161 per night from Jul 12 to Jul 13
CA $161
CA $210 total
Jul 12 - Jul 13
includes taxes & fees
8.8/10 Excellent! (1,010 reviews)
"All was fine, we’d stay there again!!"

Reviewed on Jul 6, 2026

The Farmington Inn & Suites
Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St Meriden CT
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Jul 8 to Jul 9
CA $141
CA $162 total
Jul 8 - Jul 9
includes taxes & fees
7.4/10 Good! (1,004 reviews)
"Clean room"

Reviewed on Jul 7, 2026

Red Roof Inn Meriden
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 CA $126 per night from Aug 2 to Aug 3
CA $126
CA $145 total
Aug 2 - Aug 3
includes taxes & fees
8.8/10 Excellent! (1,361 reviews)
"This was a hotel hidden that we booked at the last minute due to sustaining a power outage at our home. It is a little outdated, but room was comfortable air conditioner worked it was clean hotel smell fresh no issues."

Reviewed on Jul 6, 2026

Holiday Inn Express Southington by IHG
See all 665 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.
All Inclusive Vacations
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Frequently asked questions

How much does an Oakville vacation package cost?
You can snap up a vacation package to this top destination from CA $555 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 many days is enough for Oakville?
We suggest planning an Oakville vacation for at least 2 days. This gives you enough time to tick off key attractions such as Lake Quassapaug and Middlebury Centre Historic District, and explore neighbourhoods like Middlebury Centre Historic District and Plymouth. You might even be able to fit in one or two day trips from Oakville.
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 favourite 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.

Explore a world of travel with Expedia

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