Oakland Vacations from $892
Book a Hotel + Flight or Car together to unlock savings
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.
The Latest Oakland Vacation Packages
- Hampton Inn by Hilton Halifax Downtown
Dec 29 - Jan 4Hampton Inn by Hilton Halifax Downtown + Flight
Downtown Halifax6 nights3.0 star property8.6/10 - Excellent (1,285 reviews)"🙂"Reviewed November 7, 2026Roundtrip • Boston (BOS) - Halifax (YHZ)BOS - YHZ • Nonstop YHZ - BOS • 2 stops$1,062$892found 20 hours agoper traveler - Brewery Park Hotel
Dec 29 - Jan 4Brewery Park Hotel + Flight
North End6 nights3.5 star property9.0/10 - Wonderful (297 reviews)"We really enjoyed our stay. Very cozy and well appointed."Reviewed November 7, 2026Roundtrip • Boston (BOS) - Halifax (YHZ)BOS - YHZ • Nonstop YHZ - BOS • 2 stops$1,202$968found 1 day agoper traveler - The Hollis Halifax a DoubleTree Suites by Hilton Hotel
Dec 29 - Jan 4The Hollis Halifax a DoubleTree Suites by Hilton Hotel + Flight
Downtown Halifax6 nights4.0 star property8.8/10 - Excellent (973 reviews)Roundtrip • Boston (BOS) - Halifax (YHZ)BOS - YHZ • Nonstop YHZ - BOS • 2 stops$1,121$918found 20 hours agoper traveler - Homewood Suites by Hilton Halifax-Downtown
Dec 29 - Jan 4Homewood Suites by Hilton Halifax-Downtown + Flight
Downtown Halifax6 nights3.0 star property8.6/10 - Excellent (1,003 reviews)Roundtrip • Boston (BOS) - Halifax (YHZ)BOS - YHZ • Nonstop YHZ - BOS • 2 stops$1,134$939found 1 day agoper traveler - Residence Inn by Marriott Halifax Downtown
Dec 29 - Jan 4Residence Inn by Marriott Halifax Downtown + Flight
Downtown Halifax6 nights3.0 star property8.4/10 - Very good (1,002 reviews)"Our party of 3 stayed at the Residence Inn for 4 nights. The location was well situated for exploring the city and the room (2 bdrm suite + hide-a-bed) was very comfortable. We didn't use the kitchen, but it was nice to have. The complimentary breakfast was great and we enjoyed speaking the General Manager, Scott, who checked in with us every morning, offering suggestions and ensuring our stay was as expected. I would recommend this hotel and would stay here again, but I would note that the..."Reviewed November 5, 2026Roundtrip • Boston (BOS) - Halifax (YHZ)BOS - YHZ • Nonstop YHZ - BOS • 2 stops$1,075$895found 20 hours agoper traveler
Oakland Hotel Deals
Oak Island Resort & Conference Centre
Oak Island Resort & Conference Centre"No water pressure. Room was dirty when I arrived and was never cleaned. They took away the dirty face cloths and didn’t replace them. Won’t stay again."
Travelodge by Wyndham Bridgewater
Travelodge by Wyndham Bridgewater
Best Western Plus Bridgewater Hotel & Convention Centre
Best Western Plus Bridgewater Hotel & Convention Centre
"Great place to visit"
Days Inn & Conference Center by Wyndham Bridgewater
Days Inn & Conference Center by Wyndham Bridgewater"Room was clean but the beds are small"
Frequently Asked Questions
How much does an Oakland vacation package cost?
You'll find cheap prices from $892 on Expedia for your Oakland escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
You can typically find lower rates and greater availability in November, December and January. Explore our cheap Oakland vacation packages and you could score some great off-season discounts.
How many days is enough for Oakland?
The ideal duration for your Oakland vacation depends on what you'd like to see. Generally, a handful of days to a week will give you enough time to hit all the top sights and discover some hidden spots along the way.
How to find the best Oakland package deals?
Landing a cheap Oakland package deal is easy with Expedia. After you've entered your destination and travel dates under our "Packages" tab, set your maximum budget, apply a couple of filters and see what's available. You can tweak your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most affordable Oakland package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book an Oakland vacation as a package?
You can enjoy significant savings on your Oakland escape by booking a customized vacation package. Check the "Package" heading, then select your destination and travel dates to view some great hotel and flight 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?
If you're considering a spur-of-the-moment Oakland adventure, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can score incredible deals on your flights and hotels by booking ahead.
Does Expedia offer Book Now, Pay Later Oakland vacation packages?
Your Oakland break should be a relaxing escape from your daily routine, not a reason for money-related stress. So to give you a little more flexibility, we've partnered with online lender Affirm to bring 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 are no late payment fees or hidden costs to worry about.