Oakley Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Your Oakley Vacation
With one of our vacation packages to Oakley, you'll discover endless opportunities for fun and excitement. There's lots to look forward to, including its rural countryside and small-town feel. If your trip to Oakley includes some sightseeing, drop by well-known attractions like Lone Tree Golf Course, Brentwood Country Club and Golf Club at Brentwood. Stop dreaming and start adventuring. Explore the many options on Expedia today and finally put your Oakley vacation plans into action!
Top Oakley vacation deals
- Elm House Inn
Dec 12 - Dec 18Elm House Inn + Flight
Central Napa6 nights2.5 star property9.6/10 - Exceptional (1,658 reviews)"Great staff and a nice breakfast"Reviewed November 7, 2026Roundtrip • Toronto (YTO) - Oakland (OAK)YYZ - SFO • 1 stop SFO - YYZ • 1 stopCA $1,657CA $1,286found 1 day agoper traveller - Solage, Auberge Collection
Dec 12 - Dec 18Solage, Auberge Collection + Flight
Calistoga6 nights5.0 star property9.6/10 - Exceptional (773 reviews)Roundtrip • Toronto (YTO) - Oakland (OAK)YYZ - SFO • 1 stop SFO - YYZ • 1 stopCA $4,230CA $3,033found 1 day agoper traveller - Napa Valley Marriott Hotel & Spa
Dec 12 - Dec 18Napa Valley Marriott Hotel & Spa + Flight
Linda Vista6 nights4.0 star property8.4/10 - Very good (1,000 reviews)Roundtrip • Toronto (YTO) - Oakland (OAK)YYZ - SFO • 1 stop SFO - YYZ • 1 stopCA $1,820CA $1,334found 1 day agoper traveller - White House Napa - Adults Only
Dec 12 - Dec 18White House Napa - Adults Only + Flight
Napa Abajo6 nights4.0 star property9.2/10 - Wonderful (661 reviews)Roundtrip • Toronto (YTO) - Oakland (OAK)YYZ - SFO • 1 stop SFO - YYZ • 1 stopCA $4,402CA $3,236found 1 day agoper traveller - The Estate Yountville
Dec 12 - Dec 18The Estate Yountville + Flight
Yountville6 nights5.0 star property9.4/10 - Exceptional (1,008 reviews)Roundtrip • Toronto (YTO) - Oakland (OAK)YYZ - SFO • 1 stop SFO - YYZ • 1 stopCA $3,572CA $2,766found 1 day agoper traveller
Oakley Hotel Deals
Best Western Plus Delta Inn & Suites
Best Western Plus Delta Inn & Suites
"It sure looks like it could use some maintenance. Spots and nicks on walls and trim. Waffles are good"
Holiday Inn Express & Suites Brentwood by IHG
Holiday Inn Express & Suites Brentwood by IHG"Great breakfast offered by the price. Nothing to complain about. Great service."
Hampton Inn & Suites Pittsburg, CA
Hampton Inn & Suites Pittsburg, CA"Clean room"
Days Inn & Suites by Wyndham Antioch
Days Inn & Suites by Wyndham Antioch
Home2 Suites By Hilton Pittsburg
Home2 Suites By Hilton Pittsburg"Nice hotel. Will definitely recommend!"
Frequently Asked Questions
How much does an Oakley vacation package cost?
Offering excellent value package deals from CA $1,286 on Expedia, you'll be thrilled with how little a vacation to Oakley costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Oakley?
December, January and February are the best times to look for cheap Oakley vacation packages. Travelling in quieter periods means you can usually find better prices on flights and accommodations.
How many days is enough for Oakley?
When planning your Oakley vacation, a handful of days will be enough to tour the top spots. Make sure to check out Brentwood Family Aquatic Complex — it's one of the most popular attractions in this destination. If you're after more adventure, consider basing yourself here and going on some trips from Oakley.
How to find the best Oakley package deals?
Use Expedia's filters to help you find some terrific Oakley package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or browse for Oakley package deals in the off-season. Switch up your travel dates and you may score even better 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 Oakley vacation as a package?
You can enjoy significant savings on your next Oakley break by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to view some great hotel and flight 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 Oakley?
Secure incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Oakley escape.
How to plan a trip to Oakley?
- Choose when to get away: Check your calendar and get your bags packed. Your favourite time of year and the available activities will also help you decide when to vacation in Oakley.
- Plan your budget wisely: On top of the cost of your accommodations, you'll need to consider other expenses too. These include food, transportation and flights. Also, set aside a little extra for unexpected expenses that may arise during your trip to Oakley.
- Decide your trip length: Consider how long you'd like to spend exploring Oakley. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to pick an Oakley vacation package that brings all your bookings together.