Oakville Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to S$134 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top hotels in Oakville

Archer Hotel Napa
Archer Hotel Napa
4.5 out of 5
1230 First Street, Napa, CA
Fully refundableReserve now, pay when you stay
The price is S$399 per night from 23 Feb to 24 Feb
S$399
includes taxes & fees
23 Feb - 24 Feb
9.4/10 Exceptional! (963 reviews)
"I pretty much liked everything about the Archer. Rooms are spacious and nice, the staff is friendly and they are very dog friendly."

Reviewed on 9 Feb,2025

Archer Hotel Napa
Silverado Resort
Silverado Resort
4 out of 5
1600 Atlas Peak Road, Napa, CA
Fully refundableReserve now, pay when you stay
The price is S$408 per night from 16 Mar to 17 Mar
S$408
includes taxes & fees
16 Mar - 17 Mar
8.4/10 Very Good! (1,000 reviews)
"Great Place!"

Reviewed on 9 Feb,2025

Silverado Resort
The Sandman Hotel
The Sandman Hotel
3 out of 5
3421 Cleveland Ave, Santa Rosa, CA
Fully refundableReserve now, pay when you stay
The price is S$113 per night from 19 Feb to 20 Feb
S$113
includes taxes & fees
19 Feb - 20 Feb
8.2/10 Very Good! (2,025 reviews)
"Very clean and comfortable. Only issue was 🐜 ants in the bathroom. But it was not anything that impacted my visit!"

Reviewed on 10 Feb,2025

The Sandman Hotel
See all 1,968 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 holiday package cost?
You’ll find cheap prices on Expedia for your Oakville break. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Oakville costs.
What are the cheapest months to go to Oakville?
If you’re hoping to snag a cheap Oakville holiday package, consider planning a trip in January, February and November. You’ll typically find better prices on flights and accommodation during these quieter months — perfect for a budget-friendly break.
How many days is enough for Oakville?
The ideal duration for your Oakville holiday depends on what you’d like to do. Typically, a few days to a week will give you enough time to tick off all the major attractions and explore some hidden treasures along the way.
How to find the best Oakville package deals?
Begin your search for an Oakville package deal by entering your destination and preferred travel dates under our “Packages” tab. Then apply some filters, like “Popular locations” and “Property type,” to fine-tune the results to your exact needs. You can also sort by “Package discount” and browse offers that come with huge savings. If you don’t find the ideal Oakville package deal straight away, just play around with your dates and search again. Remember that deals are only available for a limited time, so book early and get your Oakville adventure underway.
Is it cheaper to book an Oakville holiday as a package?
You can enjoy significant savings on your Oakville retreat by booking a customised holiday package. Check the “Package” heading, then select your destination and travel dates to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Oakville?
If you’re considering a spur-of-the-moment Oakville trip, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land terrific deals on your hotels and flights by booking well in advance.
How to plan a trip to Oakville?

  1. Choose when to go: Check your diary and get packing. Your preferred season and the type of activities available will also help you decide when to holiday in Oakville.
  2. Work out your budget: Make sure you have enough money to cover everything from dining out and transportation to airfares and activities. Your hotel will likely be the largest expense during your trip to Oakville.
  3. Set the duration of your trip: Start by compiling a list of the sights and activities you want to experience in Oakville. Then, estimate how long you’ll need for each, as well as any travel time.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that’s left is to choose an Oakville holiday package that brings all your bookings together.

Popular places to visit

Napa Valley Wine Train which includes dining out and interior views as well as a small group of people

Napa Valley Wine Train

4.5/5(4 reviews)

Travel through the beautiful vineyards of Napa Valley in old-world style and enjoy gourmet dining and unbeatable scenery from your vintage railcar.

Napa Valley Wine Train
Robert Mondavi Winery

Robert Mondavi Winery

4/5(1 review)

You can enjoy a tasting or tour at Robert Mondavi Winery during your travels to Oakville. Make time for the spas and local tours in this family-friendly area.

Robert Mondavi Winery
Opus One Winery

Opus One Winery

You can enjoy a tasting or tour at Opus One Winery during your travels to Oakville. Visit the spas and top-notch restaurants in this walkable area.

Opus One Winery

What to do in Oakville

Classic Open Air Napa Valley Wine Trolley Tour

The Original Napa Valley Wine Trolley Classic Tour

S$184
per traveller
94% of travellers recommend
The Original Napa Valley Wine Trolley Classic Tour
Napa Valley: Airplane Napa Valley Tour

Napa Valley: Airplane Napa Valley Tour

S$434
per adult
Napa Valley: Airplane Napa Valley Tour
Wine Experience Day Trip to Napa & Sonoma

Wine Experience Day Trip to Napa & Sonoma

S$210
per adult
86% of travellers recommend
Wine Experience Day Trip to Napa & Sonoma
See all activities in Oakville

* 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.