Oakland Vacation Packages

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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.

Top Oakland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Loews Nashville Hotel at Vanderbilt Plaza

Loews Nashville Hotel at Vanderbilt Plaza

4 out of 5
West End
Price was CA $1,640, price is now CA $1,048 per person
CA $1,048
per person
Sep 10 - Sep 14
found 14 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Nashville (BNA)
9.2/10 Wonderful! (1,007 reviews)
Everything was excellent. I stayed for the weekend for the 4th of July celebration. As every year, we traveled from Alabama. The staff was very attentive and courteous, especially Mr. Van and a guy from the cafeteria whose name I can't remember, but he was there on Saturday afternoon.

Reviewed on Jul 5, 2026

1 Hotel Nashville

1 Hotel Nashville

5 out of 5
Downtown Nashville
Price was CA $2,812, price is now CA $1,935 per person
CA $1,935
per person
Sep 17 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Nashville (BNA)
9.4/10 Exceptional! (1,001 reviews)
Such a good stay!

Reviewed on Jul 5, 2026

Waymore's Guest House

Waymore's Guest House

3.5 out of 5
East Nashville
Price was CA $1,486, price is now CA $1,063 per person
CA $1,063
per person
Aug 5 - Aug 11
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Nashville (BNA)
9.4/10 Exceptional! (1,594 reviews)
We truly enjoyed that there was a cafe on site and also festivities to join throughout the day. The Waymore is casual, yet trendy and comfortable all at the same time. Will definitely book another stay with them❣️

Reviewed on Jul 4, 2026

Kimpton Aertson Hotel by IHG

Kimpton Aertson Hotel by IHG

4.5 out of 5
Music Row
Price was CA $1,724, price is now CA $1,248 per person
CA $1,248
per person
Sep 10 - Sep 14
found 14 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to Nashville (BNA)
9.2/10 Wonderful! (1,000 reviews)
The room was moldy smelling. The bed sheets were shorted. They didn’t move. Cold all night. Towels were thread bare in many places. Front desk was very helpful. Manager of restaurant was very friendly and helpful. Hotel needs a refresher to make me want to come back.

Reviewed on Jun 30, 2026

The Gilmore, an AvantStay Hotel

The Gilmore, an AvantStay Hotel

4 out of 5
12 South
Price was CA $2,326, price is now CA $1,687 per person
CA $1,687
per person
Sep 26 - Oct 3
found 1 day ago
Roundtrip non-stop flight included
Halifax (YHZ) to Nashville (BNA)
9.8/10 Exceptional! (548 reviews)
This was my 3rd or 4th time staying here. As always the hotel was very clean and staff are very welcoming. The hotel is in an excellent area with tons of shops and food options all within walking distance. My only negative is that the elevator can sometimes take a while due to there only being one and staff and guests both have to use it, but it’s really not that bad. Overall I would absolutely recommend this hotel to someone.

Reviewed on Jul 6, 2026

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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
The price is CA $83 per night from Jul 26 to Jul 27
CA $83
CA $94 total
Jul 26 - Jul 27
includes taxes & fees
8/10 Very good! (1,176 reviews)
"Fast check in. Room had a weird smell and holes in the sheets. Located on a main road so pretty loud outside"

Reviewed on Jul 4, 2026

Days Inn & Suites by Wyndham Bowling Green
Everhome Suites Bowling Green by Choice Hotels

Everhome Suites Bowling Green by Choice Hotels

3 out of 5
1699 Charlie Court Bowling Green KY
Fully refundableReserve now, pay when you stay
The price is CA $130 per night from Jul 13 to Jul 14
CA $130
CA $148 total
Jul 13 - Jul 14
includes taxes & fees
9.2/10 Wonderful! (139 reviews)
"Everything was wonderful. Thank you for your help."

Reviewed on Jul 6, 2026

Everhome Suites Bowling Green by Choice Hotels
Wingate by Wyndham Bowling Green

Wingate by Wyndham Bowling Green

3 out of 5
185 Greenwood Lane Bowling Green KY
Fully refundableReserve now, pay when you stay
The price is CA $115 per night from Jul 13 to Jul 14
CA $115
CA $130 total
Jul 13 - Jul 14
includes taxes & fees
8.6/10 Excellent! (1,004 reviews)
"Nice"

Reviewed on Jul 5, 2026

Wingate by Wyndham Bowling Green
See all 511 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 CA $1,048 on Expedia for your Oakland escape. However, factors like the hotel choice, length of stay and season will influence how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
To score cheap Oakland vacation packages, organize your getaway outside of peak periods such as public holidays. You'll typically find better availability and lower prices for flights and hotels.
How many days is enough for Oakland?
Usually, a handful of days is enough to explore the top sights during your Oakland vacation. However, if you prefer to have time to chill out or go on day trips, think about extending your trip.
How to find the best Oakland package deals?
Bagging a cheap Oakland package deal is a breeze with Expedia. After you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can tailor your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to discover the most affordable Oakland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book an Oakland vacation as a package?
You can enjoy significant savings on your Oakland retreat by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to view the best airfares and hotel 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 vacation package to Oakland?
Land amazing discounts by booking your flights in advance with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for an impromptu Oakland trip.
How to plan a trip to Oakland?

  1. Pick the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to go to Oakland.
  2. Work out your budget: Make sure you have enough money to pay for everything from transportation and food to airfares and activities. Your accommodations will likely be the biggest expense during your trip to Oakland.
  3. Decide your trip length: Consider how much time you want to spend discovering Oakland. Plan your days so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a tailored Oakland vacation package.

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.