Oakville Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

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 S$240 per night from 9 Aug to 10 Aug
S$240
9 Aug - 10 Aug
includes taxes & fees
9/10 Wonderful! (477 reviews)
"Always love the Chelsea. Dog friendly, great staff and amenities. Should have free nuts at the bar so as to avoiding making the bartender TELL the folks staying at the hotel, eating at the restaurant and drinking at the bar, that he has to charge $2 for the nuts. That’s embarrassing for everyone. ..."

Reviewed on 9 Jul, 2026

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
The price is S$193 per night from 26 Jul to 27 Jul
S$193
26 Jul - 27 Jul
includes taxes & fees
8.6/10 Excellent! (6,125 reviews)
"receptions need to get well trained on how to help customers."

Reviewed on 10 Jul, 2026

Holiday Inn Toronto Downtown Centre by IHG
Fairmont Royal York

Fairmont Royal York

4 out of 5
100 Front St West Toronto ON
The price is S$375 per night from 24 Jul to 25 Jul
S$375
24 Jul - 25 Jul
includes taxes & fees
9/10 Wonderful! (8,363 reviews)
"Not a luxury hotel. Slow and unhelpful staff, old musty rooms and terrible management - everything takes forever and requires extra effort - from checking in to getting a spoon in the room. They also nickel and dime you for every minor thing - like having a fridge you can use in the room. The hotel ..."

Reviewed on 10 Jul, 2026

Fairmont Royal York
See all 5,414 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.

Stay near popular Oakville attractions

Coronation Park

8.4/10 (114 reviews)
Coronation Park offers a serene lakefront escape with expansive green spaces and mature trees along Lake Ontario. Families can enjoy the accessible playground, splash pad, and picnic areas with waterfront views.
See properties

What to do in Oakville

Horseshoe Falls

Niagara Falls Day Tour from Toronto

S$90
per adult
96% of travellers recommend
Niagara Falls Day Tour from Toronto
Toronto: Casa Loma Entry Ticket

Toronto: Casa Loma Entry Ticket

S$41
per adult
90% of travellers recommend
Toronto: Casa Loma Entry Ticket
Toronto Hop-On Hop-Off Bus Tour & Free Harbour Cruise

City Sightseeing Toronto Hop-On Hop-Off Bus Tour

S$67
per adult
84% of travellers recommend
City Sightseeing Toronto Hop-On Hop-Off Bus Tour
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 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.

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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.