Oakville Holidays

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Top Flight + Hotel Deals in Oakville

Price found within the past 48 hours. Click for updated prices.
GLOBALSTAY. Gorgeous Apartments in the Heart of Toronto

GLOBALSTAY. Gorgeous Apartments in the Heart of Toronto

3.5 out of 5
Downtown Toronto
per person
20 Sept - 26 Sept
found 13 hours ago
Return flight included
Dublin (DUB) to Toronto (YYZ)
8.2/10 Very Good! (808 reviews)
Great view and clean property

Reviewed on 11 Aug 2025

Altitude Suites on Yonge

Altitude Suites on Yonge

4 out of 5
Downtown Toronto
per person
20 Sept - 26 Sept
found 13 hours ago
Return flight included
Dublin (DUB) to Toronto (YYZ)
9/10 Wonderful! (65 reviews)
Great location and very secure building. The wifi and TV was terrible. No channels and could not connect to any streaming services without freezing the whole apartment. Only 4 towels for 3 of us for 5 nights. No light I the shower in master and shower head in second bathroom sprayed everywhere.

Reviewed on 6 Aug 2025

151 Dan Leckie Way

151 Dan Leckie Way

2.5 out of 5
Downtown Toronto
per person
20 Sept - 26 Sept
found 13 hours ago
Return flight included
Dublin (DUB) to Toronto (YYZ)
9.2/10 Wonderful! (241 reviews)
I can’t rate this property as we did not stay there. They switched us property because of plumbing issues. For the property that we did stay at, the futon couch was broken and all bended. We put the mattress on the floor so we could use it as a bed. One of the bedrooms was way to tall for a rental property. There was 2 boxsprings and a mattress. The only seating there was, were barstools and bar height flimsy chairs. We had to be in all different rooms when we were at the Condo. The location was good.

Reviewed on 31 Jul 2025

Fairmont Royal York

Fairmont Royal York

4 out of 5
Downtown Toronto
per person
20 Sept - 26 Sept
found 13 hours ago
Return flight included
Dublin (DUB) to Toronto (YYZ)
9/10 Wonderful! (7,040 reviews)
The room was clean and tidy and well prepared for my arrival. Had everything I needed and was a pleasant stay.

Reviewed on 10 Aug 2025

The Sutton Place Hotel Toronto

The Sutton Place Hotel Toronto

4.5 out of 5
Downtown Toronto
per person
20 Sept - 26 Sept
found 13 hours ago
Return flight included
Dublin (DUB) to Toronto (YYZ)
9.6/10 Exceptional! (2,557 reviews)
Very nice hotel in the heart of Toronto. Close to everything you need. Good for business or pleasure. Very nice gym and pool.

Reviewed on 10 Aug 2025

Where to stay in Oakville

Find the best Oakville areas and neighborhoods for the activities you enjoy most. Learn more about Oakville
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Bronte

1 out of top 10 points of interest in this area

If you're spending some time in Bronte, Lake Ontario and Bronte Harbour are top sights worth seeing.

Find hotels in Bronte

Top hotels in Oakville

Chelsea Hotel, Toronto

Chelsea Hotel, Toronto

4 out of 5
33 Gerrard St W, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is €156 per night from 1 Sept to 2 Sept
€156
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (11,895 reviews)
"clean and safe"

Reviewed on 8 Aug 2025

Chelsea Hotel, Toronto
Holiday Inn Toronto Downtown Centre by IHG

Holiday Inn Toronto Downtown Centre by IHG

3.5 out of 5
30 Carlton Street, Toronto, ON
Fully refundable
The price is €163 per night from 1 Sept to 2 Sept
€163
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (4,403 reviews)
Great location
"First of all, Paulette in housekeeping gets 10/10. She was very friendly and pleasant. The hotel location is walking distance from a variety of restaurants and entertainment. I booked a suite for my son and I. The space was perfect size for 2 . He even had a half bathroom. There are some minor renovations ..."

Reviewed on 8 Aug 2025

Holiday Inn Toronto Downtown Centre by IHG
DoubleTree by Hilton Hotel Toronto Downtown

DoubleTree by Hilton Hotel Toronto Downtown

4 out of 5
108 Chestnut St, Toronto, ON
Fully refundableReserve now, pay when you stay
The price is €187 per night from 1 Sept to 2 Sept
€187
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (5,033 reviews)
"We had a great time. Food was delicious"

Reviewed on 10 Aug 2025

DoubleTree by Hilton Hotel Toronto Downtown
See all 4,416 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.

Popular places to visit

Rogers Centre

Rogers Centre

Come to this multipurpose stadium to watch baseball matches and football games, listen to concerts of famous bands, see family shows or simply tour this central entertainment complex.

Rogers Centre
CN Tower featuring a city, a skyscraper and skyline

CN Tower

Take the glass elevator to the lookout points on Toronto’s iconic landmark to enjoy views as far as Niagara Falls or have dinner in high style.

CN Tower
Canada's Wonderland

Canada's Wonderland

The highlight at this amusement park is the super-fast Leviathan ride, but there are 15 other roller coasters and more than 200 attractions to explore.

Canada's Wonderland

What to do in Oakville

Horseshoe Falls

Niagara Falls Day Tour from Toronto

€59
per adult
96% of travellers recommend
Niagara Falls Day Tour from Toronto
Niagara Falls Evening Tour with Boat, Dinner & Illumination Tower

Niagara Falls Evening Tour with Boat, Dinner & Illumination Tower

€75
per adult
94% of travellers recommend
Niagara Falls Evening Tour with Boat, Dinner & Illumination Tower
Niagara Falls Day Tour from Toronto with Buffet Lunch

Niagara Falls all inclusive tour with skip-the-line boat and lunch

€87
per adult
88% of travellers recommend
Niagara Falls all inclusive tour with skip-the-line boat and lunch
See all activities in Oakville

Frequently asked questions

How much does an Oakville holiday package cost?
You can pick up a holiday package to this popular destination from €1,131 on Expedia. However, how much your holiday to Oakville costs will depend on your hotel choice, length of stay and season.
What are the cheapest months to go to Oakville?
You can generally find lower prices and greater availability in January, February and March. Take a look at our cheap Oakville holiday packages and you could get some excellent off-season deals.
How many days is enough for Oakville?
To get the most out of your Oakville holiday, we suggest staying for 2 days. Divide your time between discovering Canadian Golf Hall Of Fame, Cameron's Brewing Company and other well-known attractions, on top of exploring neighbourhoods like Sheridan and Clearview. If you've got some time to spare, include a day trip or tour in your Oakville holiday itinerary.
Is it worth booking a holiday package to Oakville?
Oakville has everything you need for a wonderful getaway. Get your Oakville holiday off to a flying start by checking out top attractions like Glen Abbey Golf Course.
How to find the best Oakville package deals?
Bagging a cheap Oakville package deal is easy with Expedia. Once you've entered your destination and preferred dates under our "Packages" tab, set your maximum budget, add a couple of filters and browse what's available. You can tailor your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Oakville package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
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 car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually snag 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 type of stay, airline and car class.
When to book a holiday package to Oakville?
If you have your Oakville holiday dates finalized, book early to score some fantastic deals. With Expedia, you can generally 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 when to go: Check your calendar and pack your bags. Your preferred time of year and the type of activities available will also help you decide when to visit Oakville.
  2. Set your budget: Consider costs like transportation, flights and meals when calculating how much to put aside for your trip to Oakville. Then, select a hotel that fits your budget, whether that's an affordable option or a lavish retreat.
  3. Determine how many days away: Start by listing all the attractions and activities you want to get to in Oakville. Then, estimate how long you'll need for each, along with any travel time.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, car rental, flights and more into a personalised Oakville holiday package.

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