Oakville Vacation Packages

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  • Better together

    Save up to CA $4,200 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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Your Oakville Vacation

With all the details organized before you head off, our Oakville vacation packages mean you can concentrate on having a good time. Whether you're based in the neighborhood of Wildewood, which is great for walking, or another area, this city offers a wealth of discoveries. Fill your trip to Oakville with tours of its big-hitting attractions. Where to first? Don't miss Cape Saint Marys Marina. A few clicks is all it takes to craft a tailored Oakville vacation on Expedia.

Top Oakville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
AC Hotel by Marriott Washington DC Capitol Hill Navy Yard

AC Hotel by Marriott Washington DC Capitol Hill Navy Yard

4 out of 5
Navy Yard
Price was CA $923, price is now CA $711 per person
CA $711
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
8.8/10 Excellent! (745 reviews)
Amazing place, well located, amazing staff ready to help anytime.

Reviewed on Jul 28, 2026

Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
Historic District
Price was CA $2,013, price is now CA $1,506 per person
CA $1,506
per person
Oct 15 - Oct 18
found 18 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (1,896 reviews)

The Jefferson, Washington, DC

The Jefferson, Washington, DC

5 out of 5
Downtown Washington D.C.
Price was CA $2,323, price is now CA $1,757 per person
CA $1,757
per person
Oct 13 - Oct 16
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9.8/10 Exceptional! (1,001 reviews)
Great property

Reviewed on Jul 26, 2026

Omni Shoreham Hotel Washington DC

Omni Shoreham Hotel Washington DC

4 out of 5
Northwest
Price was CA $1,279, price is now CA $968 per person
CA $968
per person
Oct 13 - Oct 16
found 15 hours ago
Roundtrip flight included
Toronto (YTO) to Baltimore (BWI)
9/10 Wonderful! (2,409 reviews)
Didn’t appreciate how there was an extra fee in the property. The hotel should list there would be an extra $30 per day since it was booked through the third party. There was a voucher that could only be used from 4-9 PM which doesn’t make sense, it should be offered for the coffee shops etc amenities

Reviewed on Jul 28, 2026

Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was CA $1,211, price is now CA $933 per person
CA $933
per person
Sep 3 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Baltimore (BWI)
8.4/10 Very good! (1,001 reviews)

Ready to book your vacation to Oakville?

 

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Oakville Hotel Deals

avid hotel California - Lexington Park by IHG

avid hotel California - Lexington Park by IHG

3 out of 5
23274 Three Notch Road California MD
Fully refundable
The price is CA $136 per night from Aug 12 to Aug 13
CA $136
CA $151 total
Aug 12 - Aug 13
includes taxes & fees
avid hotel California - Lexington Park by IHG
La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent

3 out of 5
22769 Three Notch Rd California MD
Fully refundableReserve now, pay when you stay
The price is CA $140 per night from Aug 2 to Aug 3
CA $140
CA $155 total
Aug 2 - Aug 3
includes taxes & fees
7.8/10 Good! (1,000 reviews)
"Clean room. Easy parking."

Reviewed on Jul 26, 2026

La Quinta Inn & Suites by Wyndham Lexington Park - Patuxent
Hilton Garden Inn Solomons

Hilton Garden Inn Solomons

3 out of 5
13100 Dowell Road Solomons MD
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Aug 28 to Aug 29
CA $184
CA $204 total
Aug 28 - Aug 29
includes taxes & fees
Hilton Garden Inn Solomons
See all 297 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
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does an Oakville vacation package cost?
Offering excellent value package deals from CA $711 on Expedia, you'll be thrilled with how little a vacation to Oakville costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Oakville?
You can generally find lower rates and better availability in January, February and March. Explore our cheap Oakville vacation packages and you could get some great off-season deals.
How many days is enough for Oakville?
The ideal duration of your Oakville vacation depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to visit all the leading sights and explore some hidden gems along the way.
How to find the best Oakville package deals?
Use Expedia's filter tool to find some great Oakville package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or browse for Oakville package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book an Oakville vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customized Oakville vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Oakville?
If you have your Oakville travel dates finalized, book as soon as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Oakville?

  1. Choose when to travel: Check your calendar and get your bags packed. Your favourite time of year and the activities on offer will also help you decide when to vacation in Oakville.
  2. Set a budget: Factor in costs like transportation, flights and meals when calculating how much to set aside for your trip to Oakville. Then, pick a property that works with your budget, whether that's an economical stay or a high-end retreat.
  3. Decide how many days away: Start by listing all the activities and sights you want to get to in Oakville. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. Now all that's left is to pick an Oakville vacation package that brings all your bookings together.

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