Oakville Vacation Packages

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Your Oakville Vacation

When a fun city break is calling, answer it with a Oakville vacation package. The neighborhood of Downtown Napa, which is great for hiking, distilleries and craft breweries and cafes, makes an awesome base for your adventures. A trip to Oakville is a great opportunity to sightsee. Be sure to look around renowned attractions like Robert Mondavi Winery, V. Sattui Winery and Opus One Winery. Your ultimate Oakville vacation is a couple of clicks away. Search accommodations, flights and more on Expedia for a trip that's tailored to suit your travel style.

Top Oakville Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Bel Abri Napa Valley Inn

Bel Abri Napa Valley Inn

3 out of 5
Central Napa
Price was CA $1,305, price is now CA $996 per person
CA $996
per person
Dec 1 - Dec 6
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
9.6/10 Exceptional! (1,006 reviews)
Very nice, comfortable bed, nice breakfast, quiet.

Reviewed on Oct 30, 2026

Solage, Auberge Collection

Solage, Auberge Collection

5 out of 5
Save 100% on your flight
Price was CA $3,862, price is now CA $2,791 per person
CA $2,791
per person
Dec 1 - Dec 6
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
9.6/10 Exceptional! (768 reviews)
The best place in Napa. Solbar restaurant is excellent , great preparation on the King Salmon Don’t miss the spa and treatments there as well as the mineral and magnesium pools. Staff is so helpful and knowledgeable about wineries

Reviewed on Oct 27, 2026

Claremont Resort & Club

Claremont Resort & Club

5 out of 5
Claremont Hills
Price was CA $2,834, price is now CA $2,088 per person
CA $2,088
per person
Dec 4 - Dec 11
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
9/10 Wonderful! (1,203 reviews)
Iconic old hotel

Reviewed on Oct 27, 2026

White House Napa - Adults Only

White House Napa - Adults Only

4 out of 5
Napa Abajo
Save 100% on your flight
Price was CA $2,227, price is now CA $1,699 per person
CA $1,699
per person
Dec 1 - Dec 6
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
9.2/10 Wonderful! (660 reviews)

Napa Valley Marriott Hotel & Spa

Napa Valley Marriott Hotel & Spa

4 out of 5
Linda Vista
Price was CA $1,453, price is now CA $1,110 per person
CA $1,110
per person
Dec 1 - Dec 6
found 1 hour ago
Roundtrip flight included
Toronto (YTO) to Oakland (OAK)
8.4/10 Very good! (1,006 reviews)
The bed was very spongy and the pillows are or were overused for my liking. better mattresses and pillows should be considered. 5 out of 10

Reviewed on Oct 26, 2026

Ready to book your vacation to Oakville?

 

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Stay near popular Oakville attractions

A building with a circular top, arched doors, and a stone facade.

Opus One Winery

8.8/10 (168 reviews)
You can enjoy a tasting or tour at Opus One Winery during your travels to Oakville. Check out the spas and top-notch restaurants in this walkable area.
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What to do in Oakville

Napa Valley Wine Train: Gourmet Express Lunch or Dinner

Napa Valley Wine Train: Gourmet Express Lunch or Dinner

CA $442
per adult
100% of travellers recommend
Napa Valley Wine Train: Gourmet Express Lunch or Dinner
Redwoods & Wine Country Escape to Sonoma & Napa with Optional Gourmet Lunch

Exclusive Muir Woods, Napa & Sonoma Full-Day Wine Tour from San Francisco

CA $253
per adult
94% of travellers recommend
Exclusive Muir Woods, Napa & Sonoma Full-Day Wine Tour from San Francisco
Self-Guided Audio Driving Tour of Sonoma and Napa Valley

Self-Guided Audio Driving Tour of Sonoma and Napa Valley

CA $24
per traveller
Self-Guided Audio Driving Tour of Sonoma and Napa Valley
See all activities in Oakville

Frequently asked questions

How much does an Oakville vacation package cost?
You'll find cheap prices from CA $996 on Expedia for your Oakville getaway. However, factors like the season, choice of hotel and length of stay will determine how much your vacation to Oakville costs.
What are the cheapest months to go to Oakville?
If you're looking to book a cheap Oakville vacation package, consider travelling in January, February and November. You're likely to find better rates on flights and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Oakville?
Generally, a handful of days is enough to see the main sights during your Oakville vacation. However, if you'd like to have time to unwind or take day tours, think about extending your trip.
How to find the best Oakville package deals?
Use Expedia's handy filters to find some fabulous Oakville package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Oakville package deals in the off-season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book an Oakville vacation as a package?
You can enjoy significant savings on your Oakville break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to see the best flight and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation 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 one week before you take off. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Oakville?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Oakville.
  2. Set a budget: Factor in expenses like flights, meals and transportation when working out how much to save for your trip to Oakville. Then, choose a hotel that works with your budget, whether that's an economical option or a more upscale getaway.
  3. Work out your trip length: Think about how long you'd like to spend exploring Oakville. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, lock in the perfect Oakville vacation package for you.

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