Oakland Vacations from $786
Book a Hotel + Flight or Car together to unlock savings
Your Oakland Vacation
The fascinating city of Oakland is calling. Uncover both its hidden gems and highlights with a Oakland vacation package that's custom made for you. In the mood to explore the sights but not sure where to start? Any trip to Oakland should include Ephram White Park. Don't put off visiting this destination any longer. The perfect Oakland vacation is only a few clicks away with Expedia.
The Latest Oakland vacation packages
Price found within the past 48 hours. Click for updated prices.
Bluegreen Downtown Nashville
Downtown Nashville
$979
per person
Oct 20 - Oct 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (509 reviews)
The location was amazing. The staff was lovely and helpful. However, we did not receive any housekeeping. The hotel and the room were very clean, though. Overall, we liked our 3-night stay.
Reviewed on Aug 4, 2026
The Outrider by AvantStay
East Nashville
$1,235
per person
Oct 13 - Oct 18
found 19 hours ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.6/10 Exceptional! (19 reviews)
Lovedddd staying here!! Was the perfect spot and was so roomy. All the great stops were so close by!!!
Reviewed on Aug 7, 2026
The Hermitage Hotel
Downtown Nashville
$1,173
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9.6/10 Exceptional! (903 reviews)
We absolutely loved our 2 night stay here. The service was excellent and it was perfect as a place to stay for taking in the downtown sights.
Reviewed on Aug 2, 2026
Oakland Hotel Deals
La Quinta Inn & Suites by Wyndham Bowling Green
1953 Mel Browning Street Bowling Green KY
Fully refundableReserve now, pay when you stay
$82 nightly
$93 total
Aug 16 - Aug 17
Total with taxes and fees
8.8/10 Excellent! (1,493 reviews)
"Our room was clean & spacious. We were unable to use the amenities but breakfast was great & the staff was helpful!"
Reviewed on Aug 8, 2026
Everhome Suites Bowling Green by Choice Hotels
1699 Charlie Court Bowling Green KY
Fully refundableReserve now, pay when you stay
$92 nightly
$104 total
Sep 7 - Sep 8
Total with taxes and fees
Wingate by Wyndham Bowling Green
185 Greenwood Lane Bowling Green KY
Fully refundableReserve now, pay when you stay
$77 nightly
$87 total
Sep 6 - Sep 7
Total with taxes and fees
8.6/10 Excellent! (1,009 reviews)
"Workable Cable TV. Told it was only temporary."
Reviewed on Aug 8, 2026
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.
Find the Best Oakland Vacation Packages
Oakland Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Top Sights | National Corvette Museum, Beech Bend Park and Southern Kentucky Performing Arts Center |
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Frequently asked questions
How much does an Oakland vacation package cost?
You'll find cheap prices from $786 on Expedia for your Oakland escape. However, a range of factors like the length of stay, hotel choice and season will influence how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
November, December and January are great times to look for cheap Oakland vacation packages. Opting to travel in less busy periods means you can generally find better prices on hotels and flights.
How many days is enough for Oakland?
Typically, a handful of days is enough to see the top attractions during your Oakland vacation. However, if you'd like to have more time to relax or take day tours, think about extending your trip.
How to find the best Oakland package deals?
Begin your search for an Oakland package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to tailor 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 Oakland package deal straight away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oakland escape underway.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you considerable savings when compared to booking flights and stays separately. Better still, you can customize your Oakland trip to fit your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Oakland?
If you're planning a spur-of-the-moment Oakland adventure, browse our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can score amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
Your Oakland break should be an escape from your daily routine, not a reason for money-related stress. So to allow you extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.