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A wooden pier extending into a rocky, snow-covered shoreline with a small blue building at the end.

Dillingham Vacations from $1,085

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The Latest Dillingham Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • BBQ/picnic area
    Aug 29 - Aug 31

    Bear Paw Inn + Flight

    Dillingham
    1 night
    2.0 star property
    8.6/10 - Excellent (4 reviews)
    "Great place."
    Reviewed July 14, 2026
    Roundtrip • Oahu (HNL) - Dillingham (DLG)
    HNL - DLG • 2 stops DLG - HNL • 1 stop
    $1,124
    $1,085
    per traveler
    found 8 hours ago
    Bear Paw Inn

Dillingham Hotel Deals

BBQ/picnic area

Bear Paw Inn

Bear Paw Inn
2.0 star property
0.3 mi from Dillingham
8.6 out of 10, Excellent, (4 reviews)
"Great place."
$294 nightly
The price is $323
Jul 20 - Jul 21
Total with taxes and fees
Bear Paw Inn
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 Dillingham

Frequently Asked Questions

How much does a Dillingham vacation package cost?

You'll find cheap prices from $1,085 on Expedia for your Dillingham break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Dillingham costs.

What are the cheapest months to go to Dillingham?

If you're hoping to snag a cheap Dillingham vacation package, consider visiting in September, October and November. You'll usually find better rates on hotels and airfares during these quieter months — perfect for budget-conscious travelers.

How many days is enough for Dillingham?

Usually, a handful of days is enough to see the top sights during your Dillingham vacation. However, if you prefer to have time to kick back or take day trips, think about extending your trip.

How to find the best Dillingham package deals?

Use Expedia's filter tool to help you find some fabulous Dillingham package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or look for Dillingham package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.

Is it cheaper to book a Dillingham vacation as a package?

An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights separately. Better still, you can tailor your Dillingham trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.

When to book a vacation package to Dillingham?

Land amazing discounts by booking your flights early with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Dillingham getaway.

Does Expedia offer Book Now, Pay Later Dillingham vacation packages?

If you're like us, you love traveling but are not a fan of the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the cost of your Dillingham break across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you spot them.