Oakland Vacations from $390

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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.
Hampton Inn Nashville/Vanderbilt

Hampton Inn Nashville/Vanderbilt

2.5 out of 5
West End
Save 100% on your flight
Price was $621, price is now $390 per person
$390
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
7.4/10 Good! (1,007 reviews)
Excellent location! Within walking distance to great restaurants!

Reviewed on Aug 20, 2025

Bobby Hotel

Bobby Hotel

4 out of 5
Downtown Nashville
Price was $3,399, price is now $1,662 per person
$1,662
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
9.4/10 Exceptional! (1,000 reviews)
Not far from broadway, super convenient. Loved this hotel.

Reviewed on Aug 26, 2025

Sonesta Nashville Airport

Sonesta Nashville Airport

4 out of 5
Save 100% on your flight
Price was $1,195, price is now $685 per person
$685
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (1,702 reviews)
EVERYTHING....from reservation, check in, dining, cleanliness, attentive front desk, housekeeping, close proximity to just about anywhere you could think of going(eating, shopping, museums, night life), was OUTSTANDING!! First visit...definitely not my last!!⭐️⭐️⭐️⭐️⭐️

Reviewed on Aug 25, 2025

Virgin Hotels Nashville

Virgin Hotels Nashville

4.5 out of 5
Downtown Nashville
Save 100% on your flight
Price was $2,501, price is now $1,529 per person
$1,529
per person
Oct 9 - Oct 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Nashville (BNA)
9.4/10 Exceptional! (2,223 reviews)
Fantastic hotel. Good location. Wonderful staff.

Reviewed on Aug 27, 2025

Courtyard by Marriott Nashville Green Hills

Courtyard by Marriott Nashville Green Hills

3 out of 5
Green Hills
Save 100% on your flight
Price was $649, price is now $415 per person
$415
per person
Nov 2 - Nov 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Nashville (BNA)
9/10 Wonderful! (1,002 reviews)
The location was perfect for what we were there for. Everywhere we had to go was walkable. Easy access to the airport.

Reviewed on Aug 27, 2025

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Oakland Hotel Deals

Days Inn & Suites by Wyndham Bowling Green

Days Inn & Suites by Wyndham Bowling Green

2 out of 5
181 Cumberland Trace Rd, Bowling Green, KY
Fully refundableReserve now, pay when you stay
$59 nightly
The price is $66 total per night from Sep 14 to Sep 15
$66 total
Sep 14 - Sep 15
Total with taxes and fees
8/10 Very Good! (1,293 reviews)
"Great value for the price. Room didn’t smell great but was clean and adequate. Breakfast was basic but the price was phenomenal. No complaints."

Reviewed on Aug 21, 2025

Days Inn & Suites by Wyndham Bowling Green
Holiday Inn Express Horse Cave by IHG

Holiday Inn Express Horse Cave by IHG

2.5 out of 5
750 Flint Ridge Rd, Horse Cave, KY
Fully refundable
$104 nightly
The price is $115 total per night from Sep 2 to Sep 3
$115 total
Sep 2 - Sep 3
Total with taxes and fees
Holiday Inn Express Horse Cave by IHG
La Quinta Inn & Suites by Wyndham Bowling Green

La Quinta Inn & Suites by Wyndham Bowling Green

3 out of 5
1953 Mel Browning Street, Bowling Green, KY
Fully refundableReserve now, pay when you stay
$76 nightly
The price is $86 total per night from Aug 31 to Sep 1
$86 total
Aug 31 - Sep 1
Total with taxes and fees
8.6/10 Excellent! (1,010 reviews)
"Nice person at check in"

Reviewed on Aug 27, 2025

La Quinta Inn & Suites by Wyndham Bowling Green
See all 457 properties in Oakland
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.

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Frequently asked questions

How much does an Oakland vacation package cost?
You'll find cheap prices from $390 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.