Oakville Holidays

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to €185 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

Napa Winery Inn

Napa Winery Inn

3 out of 5
1998 Trower Ave, Napa, CA
9.2/10 Wonderful! (1,037 reviews)
"Clean, quiet, modern rooms with the most comfortable mattress I have ever slept on. Nice area next to park for a walk or jog. Pool was clean and a nice temperature. Staff checked me in and knew my name which felt very personable and friendly."

Reviewed on 24 Aug 2025

Get rates
Napa Winery Inn
Hotel Indigo Napa Valley by IHG

Hotel Indigo Napa Valley by IHG

3.5 out of 5
4195 Solano Avenue, Napa, CA
Fully refundable
The price is €157 per night from 1 Sept to 2 Sept
€157
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (1,009 reviews)
"Good."

Reviewed on 25 Aug 2025

Hotel Indigo Napa Valley by IHG
Archer Hotel Napa

Archer Hotel Napa

4.5 out of 5
1230 First Street, Napa, CA
9.4/10 Exceptional! (1,006 reviews)
"Beautiful hotel in the heart of it all. Would stay here again!"

Reviewed on 23 Aug 2025

Get rates
Archer Hotel Napa
See all 1,973 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

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

What to do in Oakville

Classic Open Air Napa Valley Wine Trolley Tour

The Original Napa Valley Wine Trolley Classic Tour

€117
per traveller
94% of travellers recommend
The Original Napa Valley Wine Trolley Classic Tour
Napa Valley Wine Train: Gourmet Express Lunch or Dinner

Napa Valley Wine Train: Gourmet Express Lunch or Dinner

€252
per adult
100% of travellers recommend
Napa Valley Wine Train: Gourmet Express Lunch or Dinner
Did we mention FUN?!

Napa Valley Small Group Winery Tour

€121
per adult
94% of travellers recommend
Napa Valley Small Group Winery Tour
See all activities in Oakville

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.

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