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
- Napa Valley Marriott Hotel & Spa
Jan 8 - Jan 12Napa Valley Marriott Hotel & Spa + Flight
Linda Vista4 nights4.0 star property8.4/10 - Very good (1,000 reviews)Roundtrip • Toronto (YTO) - Oakland (OAK)YYZ - OAK • 2 stops OAK - YYZ • 2 stopsCA $1,501CA $1,171found 4 hours agoper traveller - Archer Hotel Napa
Jan 13 - Jan 17Archer Hotel Napa + Flight
Downtown Napa4 nights4.5 star property9.6/10 - Exceptional (1,411 reviews)Roundtrip • Edmonton (YEG) - Oakland (OAK)YEG - OAK • 2 stops OAK - YEG • 2 stopsCA $2,031CA $1,559found 1 day agoper traveller - Carneros Resort and Spa
Jan 8 - Jan 12Carneros Resort and Spa + Flight
Napa4 nights5.0 star property9.2/10 - Wonderful (395 reviews)Roundtrip • Toronto (YTO) - Oakland (OAK)YYZ - OAK • 2 stops OAK - YYZ • 2 stopsCA $3,337CA $2,602found 4 hours agoper traveller - White House Napa - Adults Only
Jan 13 - Jan 17White House Napa - Adults Only + Flight
Napa Abajo4 nights4.0 star property9.2/10 - Wonderful (661 reviews)Roundtrip • Edmonton (YEG) - Oakland (OAK)YEG - OAK • 2 stops OAK - YEG • 2 stopsCA $2,190CA $1,731found 1 day agoper traveller - The Estate Yountville
Jan 8 - Jan 12The Estate Yountville + Flight
Yountville4 nights5.0 star property9.4/10 - Exceptional (1,007 reviews)"Pros: walkable, awesome breakfast every morning -truly fantastic, rooms clean and spacious. Snacks available in the lobby throughout the day. The car service was also very nice. Cons: The resort fee is high. Not sure why that isn’t just rolled into the nightly cost, bit deceiving. Spa was closed."Reviewed November 4, 2026Roundtrip • Toronto (YTO) - Oakland (OAK)YYZ - OAK • 2 stops OAK - YYZ • 2 stopsCA $2,915CA $2,316found 4 hours agoper traveller
Discover the most popular places to visit in Oakville
What to do in Oakville
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Oakville Hotel Deals
"Clean, immaculate, well appointed and convenient to tons of vineyards in the area."
"Such a cozy, beautiful place to stay! Absolutely loved every part of my stay at Rancho Caymus!"
"very clean and spacious room. photo of the room had lovely vaulted ceiling however our room did not - i think ground floor does not and upper does. the hotel expanded some years ago and felt like they had taken over an old apartment complex so you - i did not like that feeling. lobby and bar very dark - could do with an interior design update."
"Overpriced for what you get."
"Such a beautiful and relaxing stay."
"Great central location to wine tasting! Love the town of St Helena! Was nice to have water in carafe in room and excellent Italian espresso! Breakfast is served to you in your room per breakfast order placed night before. Was great service right on time as requested 7am and excellent choices with carafe of coffee and fresh fruit. Plus spa is access to use sauna, steam room etc no booking necessary. Would definitely stay here again!"
"It rained one day and the ceiling over the bed leaked. Not terribly but enough to be an annoyance. Otherwise our stay in the Caboose was fine. Especially for the price in the area. A genuine good value. If all you need is a good nights sleep I recommend it here. (When it’s not raining)"
"Great location to visit wineries in the Napa area. Rooms are neat and clean. Great light breakfast offerings before starting your adventure."
Frequently Asked Questions
How much does an Oakville vacation package cost?
You'll find cheap prices from CA $1,171 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?
- 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.
- 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.
- 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.
- Bundle your airfare and accommodations: Once you've settled on your trip dates and duration, lock in the perfect Oakville vacation package for you.