Diamond Holidays

Photo by Glenn Miller

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Diamond

DoubleTree by Hilton Hotel Portland

DoubleTree by Hilton Hotel Portland

4 out of 5
1000 NE Multnomah Street, Portland, OR
Fully refundableReserve now, pay when you stay
The price is S$177 per night from 24 Aug to 25 Aug
S$177
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,016 reviews)
"Great time"

Reviewed on 13 Aug, 2025

DoubleTree by Hilton Hotel Portland
Courtyard by Marriott Portland City Center

Courtyard by Marriott Portland City Center

3.5 out of 5
550 SW Oak Street, Portland, OR
Fully refundable
The price is S$155 per night from 24 Aug to 25 Aug
S$155
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (1,907 reviews)
"Great hotel and staff, but unfortunately noisy through the night - traffic and people. Typical for a larger city downtime location."

Reviewed on 13 Aug, 2025

Courtyard by Marriott Portland City Center
The Paramount Hotel

The Paramount Hotel

3.5 out of 5
808 SW Taylor St, Portland, OR
Fully refundableReserve now, pay when you stay
The price is S$155 per night from 1 Sept to 2 Sept
S$155
1 Sept - 2 Sept
includes taxes & fees
9.2/10 Wonderful! (2,687 reviews)
"Loved every minute here!!! Thank you so much!"

Reviewed on 13 Aug, 2025

The Paramount Hotel
See all 18,160 properties in Oregon
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 a Diamond holiday package cost?
You'll find cheap prices on Expedia for your Diamond escape. However, a range of factors like the length of stay, the season and your choice of hotel will influence how much your holiday to Diamond costs.
What are the cheapest months to go to Diamond?
You can usually find reduced prices and greater availability in January, February and November. Take a look at our cheap Diamond holiday packages and you could score some great off-season discounts.
How many days is enough for Diamond?
Usually, a handful of days is enough to tick off the top sights during your Diamond holiday. But if you prefer to have some time to chill out or take day tours, consider extending your trip.
How to find the best Diamond package deals?
Use Expedia's filters to find some fabulous Diamond package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Diamond package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your holiday package as early as possible.
Is it cheaper to book a Diamond holiday as a package?
Expedia holiday packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the flexibility to create a customised Diamond holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Diamond?
Enjoy incredible bargains by reserving your flights early with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Diamond adventure.
How to plan a trip to Diamond?

  1. Choose when to go: Check your calendar and get your bags packed. Your preferred time of year and the available activities will also help you decide when to visit Diamond.
  2. Figure out your budget: Make sure you have enough money to pay for everything from transportation and food to activities and flights. Your hotel will likely be the biggest expense during your trip to Diamond.
  3. Decide how long to go for: Now that you're up to speed on Diamond, you can work out the perfect length of your break. Pull together a draft itinerary and allocate enough time for all the things you want to do.
  4. Combine your airfare and accommodation: After you've nailed down your dates and duration, book the perfect Diamond holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.