Trail Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Kaitlin Walters
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    Better together
    Save up to NZ$616 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

Trail Holiday

Our pick of the best Trail Hotel Deals

Romantic & private cabin on Rogue River, 1 hr from Crater Lake
Romantic & private cabin on Rogue River, 1 hr from Crater Lake
Trail
9.8/10 Exceptional! (390 reviews)
Fantastic Getaway for any occaision
"Took me and my lady and our dog here for a nice getaway from our hectic lives. This spa offers everything that you need and more if you want pristine natural beauty with all the comforts of a resort. We brought all of our own food with us to cook for dinner and breakfast and have no problem easily ..."

Reviewed on 16 May 2025

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Romantic & private cabin on Rogue River, 1 hr from Crater Lake
"Home on The Rogue" - Gateway to Crater Lake!
"Home on The Rogue" - Gateway to Crater Lake!
Trail
9.8/10 Exceptional! (86 reviews)
Quilt Retreat
"We came to Oregon to attend a quilt retreat. This is our 2nd year to stay in this house. It is minutes from the grange hall we did our retreat in. The house has a beautiful view of the river. We enjoy watching the fishermen drift by in the morning. The house is very clean and has everything you need ..."

Reviewed on 21 May 2025

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"Home on The Rogue" - Gateway to Crater Lake!
Fully equipped house on the river with a private fishing hole.
Fully equipped house on the river with a private fishing hole.
Trail
Lovely riverfront house
"Fabulous location on the river with clean, well kept and equipped house."

Reviewed on 25 Jul. 2024

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Fully equipped house on the river with a private fishing hole.
See all 155 properties in Trail
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 Trail holiday package cost?
You'll find cheap prices on Expedia for your Trail 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 Trail costs.
What are the cheapest months to go to Trail?
Plan your getaway for the off-season and you're likely to get cheap Trail holiday packages. Remember that school holiday periods and major local events can impact prices, so do some research before booking.
How many days is enough for Trail?
The ideal duration for your Trail holiday depends on what you'd like to do and see. Usually, a few days to a week will give you plenty of time to check out all the main attractions and explore some hidden gems along the way.
How to find the best Trail package deals?
Begin your search for a Trail package deal by entering your destination and preferred travel dates under our "Packages" tab. Then select a few filters, like "Popular locations" and "Property type," to tailor the results to your exact needs. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Trail package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Trail escape underway.
Is it cheaper to book a Trail holiday as a package?
You can enjoy significant savings on your Trail break by booking a tailored holiday package. Click on the "Package" heading, then select your travel dates and destination to browse the best hotel prices and airfares. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a holiday package to Trail?
If you have your Trail travel dates locked in, book early to snap up some awesome deals. With Expedia, you can generally reserve some flights up to one year ahead of time. Prefer spontaneous adventures? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Trail?

  1. Choose when to go: Check your schedule and pack your bags. Your favourite time of year and the available activities will also help you decide when to escape to Trail.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to activities and airfares. Your hotel will probably be the largest expense during your trip to Trail.
  3. Work out your trip length: Consider how much time you want to spend exploring Trail. Plan your itinerary so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your car rental, hotels, flights and more into a personalised Trail holiday package.

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