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.
Executive Inn & Suites Embarcadero Cove

Executive Inn & Suites Embarcadero Cove

San Antonio
CA $800
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Oakland (OAK)
9/10 Wonderful! (1,219 reviews)
Clean, good breakfast and nice staff.

Reviewed on Sep 15, 2026

White House Napa

White House Napa

Napa Abajo
CA $1,103
per person
Nov 23 - Nov 26
found 7 hours ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
9.2/10 Wonderful! (648 reviews)
Be prepared for noisy people coming through the front door late in the evening. Bring ear plugs.

Reviewed on Sep 14, 2026

Hilton Garden Inn San Francisco/Oakland Bay Bridge

Hilton Garden Inn San Francisco/Oakland Bay Bridge

CA $912
per person
Oct 19 - Oct 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Oakland (OAK)
8.8/10 Excellent! (1,251 reviews)
Claremont Resort & Club

Claremont Resort & Club

Claremont Hills
CA $1,394
per person
Nov 5 - Nov 8
found 10 hours ago
Roundtrip non-stop flight included
Vancouver (YVR) to Oakland (OAK)
9/10 Wonderful! (1,102 reviews)
This hotel is considered 5-star, but it acts like a 3-star, especially the pool area. It's just really a country club that happens to have hotel rooms because there's no regard for the hotel guests. The chairs are pressed together, literally pressed together. There's no regard for personal space. People have kids' classes going on all day long, and today, to top it off, they have construction. The room smelled musty, and I'll have to say that the food in the dining room, although it has a lovely setup on the balcony outside, is very expensive and beyond mediocre. The place, in my opinion, is way overpriced. At $500 a night,I expect a lot more, and I've seen a lot more for $500 a night. I'm surprised that it gets booked so often because, at one point, somebody's got to step back and say, "Enough is enough."

Reviewed on Sep 15, 2026

Lavender, A Four Sisters Inn

Lavender, A Four Sisters Inn

CA $1,307
per person
Nov 23 - Nov 26
found 7 hours ago
Roundtrip flight included
Calgary (YYC) to Oakland (OAK)
8.8/10 Excellent! (448 reviews)
I would definitely stay here again. They were very helpful and attentive but not in the way. It's a very quiet place just off the main road that runs through town. I loved sitting on the porch in the mornings and drinking my coffee. Close to everything we wanted to see in the valley.

Reviewed on Aug 10, 2026

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Oakville Hotel Deals

Oxford Suites Sonoma County

Oxford Suites Sonoma County

67 Golf Course Drive W. Rohnert Park CA
Fully refundableReserve now, pay when you stay
CA $174
CA $214 total
Sep 22 - Sep 23
includes taxes & fees
Oxford Suites Sonoma County
Archer Hotel Napa

Archer Hotel Napa

1230 First Street Napa CA
CA $469
CA $540 total
Sep 21 - Sep 22
includes taxes & fees
Archer Hotel Napa
Casa Mani Resort Napa Valley, Curio Collection by Hilton

Casa Mani Resort Napa Valley, Curio Collection by Hilton

1075 California Blvd Napa CA
Fully refundableReserve now, pay when you stay
CA $513
CA $591 total
Sep 20 - Sep 21
includes taxes & fees
Casa Mani Resort Napa Valley, Curio Collection by Hilton
See all 2,051 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

Large wooden fermentation tanks in a brewery.
Photo by There & Back Again

Robert Mondavi Winery

8.8/10 (687 reviews)
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 romantic area.
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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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A tree-lined street with yellow leaves.

Far Niente Winery

You can enjoy a tasting or tour at Far Niente Winery during your travels to Oakville. Amble around this romantic area's picturesque gardens, or seek out the local tours.
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Cardinale Estate Winery

You can enjoy a tasting or tour at Cardinale Estate Winery during your travels to Oakville. Amble around this family-friendly area's picturesque gardens, or seek out the local tours.
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Rudd Winery & Vineyards

You can enjoy a tasting or tour at Rudd Winery & Vineyards during your travels to Oakville. Make time for the spas and local tours in this romantic area.
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Welcome to Napa Valley Sign

You can learn about the history of Oakville with a trip to Welcome to Napa Valley Sign. Discover the area's mountain views and monuments.
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Folie a Deux

Take the family on an outing to Folie a Deux during your trip to Oakville. Make time for the spas and local tours in this walkable area.
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Nickel & Nickel Winery

You can enjoy a tasting or tour at Nickel & Nickel Winery during your travels to Oakville. Discover the area's mountain views and monuments.
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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 $384
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 $223
per adult
94% of travellers recommend
Exclusive Muir Woods, Napa & Sonoma Full-Day Wine Tour from San Francisco
Classic Open Air Napa Valley Wine Trolley Tour

The Original Napa Valley Wine Trolley Classic Tour

CA $201
per traveller
94% of travellers recommend
The Original Napa Valley Wine Trolley Classic Tour
See all activities in Oakville

Frequently asked questions

How much does an Oakville vacation package cost?
You'll find cheap prices from CA $800 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.