Diamond Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top hotels in Diamond

Riverhouse Lodge

Riverhouse Lodge

3.5 out of 5
3075 N. Business 97 Bend OR
Fully refundableReserve now, pay when you stay
The price is S$294 per night from 13 Jul to 14 Jul
S$294
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (1,249 reviews)
"Good location, nice facility, but the buildings interiors were outdated. The one disappointing factor was 95° outside and our air conditioner in our room did not work."

Reviewed on 10 Jul, 2026

Riverhouse Lodge
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$160 per night from 9 Aug to 10 Aug
S$160
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (3,531 reviews)
"Fantastic"

Reviewed on 10 Jul, 2026

The Paramount Hotel
Tolovana Inn

Tolovana Inn

2.5 out of 5
3400 S. Hemlock Cannon Beach OR
Fully refundableReserve now, pay when you stay
The price is S$293 per night from 23 Jul to 24 Jul
S$293
23 Jul - 24 Jul
includes taxes & fees
8.8/10 Excellent! (2,031 reviews)
"Nice location next to the beach."

Reviewed on 11 Jul, 2026

Tolovana Inn
See all 19,111 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.

Stay near popular Diamond attractions

Diamond Craters Outstanding Natural Area

8.6/10 (4 reviews)
This 17,000-acre volcanic wonderland showcases diverse basaltic formations from craters to lava tubes. Explore the geological marvels while hiking through unspoiled terrain—just remember to bring water.
See properties

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.

Explore a world of travel with Expedia

* 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.