Oakland Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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Your Oakland Vacation

Our vacation packages to Oakland give you countless opportunities to delve into new sights, sounds and sensations. And with all the travel planning worked out, you can breathe easy and enjoy your city getaway without a worry in the world. Every trip to Oakland needs a well-designed itinerary. Fill yours with leading attractions like Campgaw Mountain Ski Area, High Mountain Park and Lake Erskine. Stop daydreaming and start adventuring. Explore the range of options on Expedia today and put your Oakland vacation plans into action!

Top Oakland Vacation Deals

Price found within the past 48 hours. Click for updated prices.
JW Marriott Essex House New York

JW Marriott Essex House New York

4.5 out of 5
Manhattan
Price was CA $2,033, price is now CA $1,114 per person
CA $1,114
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8.8/10 Excellent! (1,001 reviews)

Eurostars Wall Street

Eurostars Wall Street

4 out of 5
Manhattan
Price was CA $4,996, price is now CA $2,900 per person
CA $2,900
per person
Dec 26 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
8/10 Very good! (1,000 reviews)
Cons: Air conditioning never really worked well. Thankfully opening the window helped. It's kind of set up like an apartment so there isn't an ice machine on the floor. The TV was tiny and hard to watch. Breakfast wasn't complimentary ($19 per person). IDK for $2200 I expected a higher caliber of service and amenities. Pros: The staff was always helpful. The location is convenient especially for things downtown close the the financial district.

Reviewed on Nov 3, 2026

Eurostars The Chemists’ Club Hotel

Eurostars The Chemists’ Club Hotel

4 out of 5
Manhattan
Price was CA $2,738, price is now CA $1,620 per person
CA $1,620
per person
Jan 10 - Jan 15
found 20 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New York (JFK)
9.4/10 Exceptional! (555 reviews)

1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Price was CA $4,385, price is now CA $2,813 per person
CA $2,813
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9/10 Wonderful! (1,002 reviews)

Mandarin Oriental, New York

Mandarin Oriental, New York

5 out of 5
Manhattan
Price was CA $5,180, price is now CA $3,334 per person
CA $3,334
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New York (JFK)
9.2/10 Wonderful! (673 reviews)
Excellent stay

Reviewed on Oct 26, 2026

Ready to book your vacation to Oakland?

 

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Oakland Hotel Deals

Garner Hotel North Bergen - NYC Gateway by IHG

Garner Hotel North Bergen - NYC Gateway by IHG

3 out of 5
2750 Tonnelle Ave North Bergen NJ
Fully refundable
The price is CA $154 per night from Nov 16 to Nov 17
CA $154
CA $181 total
Nov 16 - Nov 17
includes taxes & fees
Garner Hotel North Bergen - NYC Gateway by IHG
La Quinta Inn & Suites by Wyndham Clifton/Rutherford

La Quinta Inn & Suites by Wyndham Clifton/Rutherford

3 out of 5
265 Route 3 East Clifton NJ
Fully refundableReserve now, pay when you stay
The price is CA $165 per night from Nov 23 to Nov 24
CA $165
CA $189 total
Nov 23 - Nov 24
includes taxes & fees
La Quinta Inn & Suites by Wyndham Clifton/Rutherford
World of Blue

World of Blue

4 out of 5
2 Meadowlands Plaza East Rutherford NJ
Fully refundableReserve now, pay when you stay
The price is CA $234 per night from Nov 16 to Nov 17
CA $234
CA $276 total
Nov 16 - Nov 17
includes taxes & fees
World of Blue
See all 2,009 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Stay near popular Oakland attractions

Crystal Lake Beach Club

Why not spend a lazy afternoon at Crystal Lake Beach Club during your trip to Oakland? Amble around the area's forest or visit its shops.
See properties

Frequently asked questions

How much does an Oakland vacation package cost?
You'll find cheap prices from CA $1,114 on Expedia for your Oakland break. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Oakland costs.
What are the cheapest months to go to Oakland?
If you're hoping to snag a cheap Oakland vacation package, consider planning a trip in January, February and March. You'll typically find lower rates on accommodations and flights during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Oakland?
The ideal length for your Oakland vacation depends on what you'd like to see and do. Usually, a handful of days to a week will give you plenty of time to go to all the main attractions and discover some hidden gems along the way.
How to find the best Oakland package deals?
Landing a cheap Oakland package deal is easy with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your budget, add a couple of filters and see what's available. You can fine-tune your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Oakland package deals. Want a simple trick to get even more savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are often lower.
Is it cheaper to book an Oakland vacation as a package?
An Expedia vacation package could land you great savings when compared to booking accommodations and flights individually. Better still, you can customize your Oakland escape to match your exact style. Choose your preferred flight time, select the hotel type and add a rental car. Explore our bundles to see how much you can save.
When to book a vacation package to Oakland?
If you've got your Oakland vacation dates finalized, book as soon as you can to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for travelling on a whim.
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. Plan your budget wisely: In addition to the price of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, put aside a little extra for unexpected expenses that may come up during your trip to Oakland.
  3. Work out your trip length: Consider how long you'd like to spend discovering Oakland. Plan your days so you can get to all the attractions and activities you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, flights, hotels and more into a customized Oakland vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.