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A rocky shoreline with a forested area and a calm sea.

Oakland Vacations from $713

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The Latest Oakland Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Rowing
    Sep 24 - Sep 30

    Hearthstone Inn Boutique Hotel Halifax - Dartmouth + Flight

    Dartmouth
    6 nights
    3.5 star property
    7.4/10 - Good (1,174 reviews)
    "​Great location, clean rooms, and included breakfast. ​The main downside was an unexpected $50 deposit charged at check-in that was never mentioned during booking. At checkout, the front desk had no record of the payment until I showed my receipt. They refunded it without further issue, but the confusion was unsettling. Keep your receipts!"
    Reviewed July 19, 2026
    Roundtrip • Boston (BOS) - Halifax (YHZ)
    BOS - YHZ • Nonstop YHZ - BOS • 1 stop
    $867
    $713
    per traveler
    found 22 hours ago
    Hearthstone Inn Boutique Hotel Halifax - Dartmouth
  • Front of property
    Sep 24 - Sep 30

    Coastal Inn Halifax + Flight

    Halifax
    6 nights
    3.0 star property
    8.6/10 - Excellent (1,002 reviews)
    Roundtrip • Boston (BOS) - Halifax (YHZ)
    BOS - YHZ • Nonstop YHZ - BOS • 1 stop
    $1,027
    $792
    per traveler
    found 22 hours ago
    Coastal Inn Halifax
  • Bar (on property)
    Sep 24 - Sep 30

    Future Inns Halifax + Flight

    Clayton Park West
    6 nights
    3.0 star property
    9.2/10 - Wonderful (2,306 reviews)
    Roundtrip • Boston (BOS) - Halifax (YHZ)
    BOS - YHZ • Nonstop YHZ - BOS • 1 stop
    $1,009
    $808
    per traveler
    found 22 hours ago
    Future Inns Halifax
  • Exterior
    Sep 24 - Sep 30

    Atlantica Hotel Halifax + Flight

    South End
    6 nights
    4.0 star property
    8.6/10 - Excellent (1,322 reviews)
    Roundtrip • Boston (BOS) - Halifax (YHZ)
    BOS - YHZ • Nonstop YHZ - BOS • 1 stop
    $1,377
    $1,116
    per traveler
    found 22 hours ago
    Atlantica Hotel Halifax
  • Reception
    Sep 24 - Sep 30

    Chateau Bedford, Trademark Collection by Wyndham + Flight

    Birch Cove
    6 nights
    4.0 star property
    9.2/10 - Wonderful (2,216 reviews)
    Roundtrip • Boston (BOS) - Halifax (YHZ)
    BOS - YHZ • Nonstop YHZ - BOS • 1 stop
    $1,099
    $893
    per traveler
    found 22 hours ago
    Chateau Bedford, Trademark Collection by Wyndham

Oakland Hotel Deals

Exterior

Miller House By the Bay

Miller House By the Bay
2.0 star property
1.1 mi from Oakland
9.8 out of 10, Exceptional, (176 reviews)
"Such a lovely, warm welcome by very kind ladies. The bed was SO comfortable, the balcony was amazing! Thank you for sharing your lovely home with us!"
$109 nightly
The price is $124
Jul 26 - Jul 27
Total with taxes and fees
Miller House By the Bay
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.
See all properties in Oakland

Frequently Asked Questions

How much does an Oakland vacation package cost?

You'll find cheap prices from $713 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.