Oakville Holidays

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Top hotels in Oakville

Archer Hotel Napa

Archer Hotel Napa

1230 First Street Napa CA
Fully refundableReserve now, pay when you stay
S$353
7 Sept - 8 Sept
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
S$481
31 Aug - 1 Sept
includes taxes & fees
9.4/10 Exceptional! (105 reviews)
"The rooms were recently updated, the bathrooms had jets in the shower, and an automatic toilet. Very clean."

Reviewed on 24 Aug, 2026

Casa Mani Resort Napa Valley, Curio Collection by Hilton
Silverado Resort

Silverado Resort

1600 Atlas Peak Road Napa CA
Fully refundableReserve now, pay when you stay
S$525
30 Aug - 31 Aug
includes taxes & fees
9/10 Wonderful! (1,187 reviews)
"We Love Silverado! Everything was lovely!"

Reviewed on 26 Aug, 2026

Silverado Resort
See all 2,063 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)
This pioneering winery established Napa Valley as a world-class wine region with its exceptional vintages. Enjoy immersive tastings led by expert staff while exploring curated art collections in an elegant setting.
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A building with a circular top, arched doors, and a stone facade.

Opus One Winery

8.8/10 (168 reviews)
Born from the legendary partnership of Robert Mondavi and Baron de Rothschild, Opus One crafts Napa's most celebrated Bordeaux-style blends. Reserve an intimate tasting for panoramic valley views and exceptional wines.
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A tree-lined street with yellow leaves.

Far Niente Winery

This historic 1885 estate showcases Napa Valley's finest Chardonnay and Cabernet Sauvignon in a stunning setting. Explore the atmospheric wine caves before enjoying a seated tasting with artisanal cheese pairings.
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Cardinale Estate Winery

Cardinale Estate crafts a single, exceptional Cabernet Sauvignon blend showcasing Napa Valley's diverse terroirs. Enjoy an intimate tasting with culinary pairings and panoramic valley views.
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Welcome to Napa Valley Sign

You can learn about the history of Oakville when you stop by Welcome to Napa Valley Sign. Discover the area's mountain views and monuments.
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Rudd Winery & Vineyards

This boutique Oakville estate crafts wines showcasing Napa Valley's distinctive terroir. Enjoy an intimate tasting amid picturesque vineyards, but remember appointments are required for this exclusive visit.
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Folie a Deux

Famed for its Menage à Trois collection, Folie à Deux Winery offers tastings in a tranquil Napa Valley setting. Bring a picnic to enjoy among the vineyards while sampling their renowned red, white, and rosé blends.
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Turnbull Winery

This Napa Valley estate showcases exceptional Cabernet Sauvignon amid a gallery of fine black and white photography. Reserve a private tasting to sample their premium wines while overlooking picturesque vineyards.
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What to do in Oakville

Redwoods & Wine Country Escape to Sonoma & Napa with Optional Gourmet Lunch

Redwoods & Wine Country Escape to Sonoma & Napa with Optional Gourmet Lunch

S$231
per adult
94% of travellers recommend
Redwoods & Wine Country Escape to Sonoma & Napa with Optional Gourmet Lunch
Napa Valley Wine Train: Gourmet Express Lunch or Dinner

Napa Valley Wine Train: Gourmet Express Lunch or Dinner

S$412
per adult
100% of travellers recommend
Napa Valley Wine Train: Gourmet Express Lunch or Dinner
Classic Open Air Napa Valley Wine Trolley Tour

The Original Napa Valley Wine Trolley Classic Tour

S$187
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 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.

Explore a world of travel with Expedia

* 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.