Oakland 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*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Oakland Vacation
Book a custom vacation package to Oakland and prepare to experience this interesting city the way you want. Consider staying in the neighborhood of Garden Lots, which is good for watersports and a whole lot more. Fill your trip to Oakland with visits to some of its most popular attractions. Where to first? Head straight for Halifax and Southwestern Railway Museum. Don't put off exploring this destination any longer. The perfect Oakland vacation is a few quick clicks away with Expedia.
Top Oakland Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hearthstone Inn Boutique Hotel Halifax - Dartmouth
CA $582
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
7.4/10 Good! (1,204 reviews)
Although the room was clean, the hotel itself is pretty old and has not been properly maintained. The staff seem to have been only doing their jobs and cared less for the comfort of the guests. There is no room service.
Reviewed on Aug 11, 2026
Brewery Park Hotel
North End
CA $879
per person
Nov 5 - Nov 9
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
9.2/10 Wonderful! (268 reviews)
We stayed at this property for one night. It is more like an Airbnb than a hotel. Our unit was located on the first floor on top of a coffee shop. Access to the property is through passcodes and there are no staff. There is no elevator in the property and there were 15-20 stairs to reach each floor. We didn’t mind climbing the stairs but it can be a challenging for some people. The room was very clean. Mattress was queen size but very comfy. Bedding were clean too. There was a leak from AC in the room making a wet floor which was a bit disappointing. There are no parking spots on the property and we had to park by the street across the property.
Reviewed on Aug 10, 2026
Ready to book your vacation to Oakland?
Oakland Hotel Deals
Travelodge by Wyndham Bridgewater
49 North St Bridgewater NS
Fully refundableReserve now, pay when you stay
CA $184
CA $223 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,023 reviews)
"Me and my boyfriend were checking in for a wedding and they were extremely accommodating. We messed up and didn’t realize that you had to call in advance for early check in but they still tried to make it work so we were on time for the wedding, even after they were short staffed. Front desk was ..."
Reviewed on Aug 11, 2026
Bridgewater Hotel
35 High St. Bridgewater NS
Fully refundableReserve now, pay when you stay
CA $137
CA $161 total
Aug 25 - Aug 26
includes taxes & fees
6/10 (465 reviews)
"The staff is wonderful and care about the customer. When there were towels missing, they sent them to room before I requested. The overall condition is not good, but I saw renovation projects took places. I hope they could finish the project soon."
Reviewed on Aug 11, 2026
Best Western Plus Bridgewater Hotel & Convention Centre
527 Highway 10 Exit 12 Cookville NS
Fully refundableReserve now, pay when you stay
CA $246
CA $281 total
Sep 3 - Sep 4
includes taxes & fees
9.2/10 Wonderful! (1,017 reviews)
"Just wow! Great staff! Great service! Great pool for the kids! Side by side room as requested. It was perfect! Soooo clean"
Reviewed on Aug 11, 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.
Frequently asked questions
How much does an Oakland vacation package cost?
You can snap up a vacation package to this top destination from CA $582 on Expedia. However, how much your vacation to Oakland costs will depend on the length of stay, hotel choice and season.
What are the cheapest months to go to Oakland?
If you're hoping to book a cheap Oakland vacation package, consider visiting in January, February and November. You'll generally find better rates on hotels and flights during these quieter months — perfect for budget-conscious travellers.
How many days is enough for Oakland?
With a well-planned itinerary, you can easily tick off the main Oakland attractions in a handful of days. But if you prefer to discover hidden spots or go on day tours, think about booking your Oakland vacation for longer.
How to find the best Oakland package deals?
Use Expedia's handy filters to help you find some fabulous Oakland package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Oakland package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you significant savings when compared to arranging hotels and flights individually. Better still, you can tailor your Oakland escape to fit your exact needs. Pick your preferred flight time, select the hotel type and add a rental car. Check out our great deals to see how much you can save.
When to book a vacation package to Oakland?
If you've got your Oakland travel dates confirmed, book as soon as you can to score some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are great for travelling on a whim.
How to plan a trip to Oakland?
- Choose your travel dates: The things you plan to do in Oakland and your favourite season will help you decide when to go.
- Figure out your budget: Make sure you have enough money to cover everything from transportation and meals to flights and experiences. Your hotel will likely be the largest expense during your trip to Oakland.
- Set the duration of your trip: Start by compiling a list of the attractions you'd like to experience in Oakland. Then, estimate how long you'll need at each, as well as any travel time.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find an Oakland vacation package that brings all your bookings together.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
