Trail Holidays

Photo by Kaitlin Walters

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Top hotels in Trail

"Home on The Rogue" - Gateway to Crater Lake!

"Home on The Rogue" - Gateway to Crater Lake!

Trail
9.8/10 Exceptional! (87 reviews)
Beautiful location
"House was as advertised"

Reviewed on 1 Jul 2025

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"Home on The Rogue" - Gateway to Crater Lake!
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! (392 reviews)
"This was an awesome place to stay. The picture of the river from the deck is 100% accurate. We enjoyed sitting and relaxing on the deck each morning. A couple suggestions: use fragrance free laundry soap for those of us that have sensitivities - luckily I bring my own pillow case just in case. And ..."

Reviewed on 13 Jul 2025

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Romantic & private cabin on Rogue River, 1 hr from Crater Lake
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!

Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!

Trail
The price is €196 per night from 26 Aug to 27 Aug
€196
26 Aug - 27 Aug
includes taxes & fees
9.4/10 Exceptional! (11 reviews)
Cozy, quite get-a-way
"Property was amazingly gorgeous, exactly as described, pet friendly, check-in process was simple.....would highly recommend both the room and host. Extraordinary experience!"

Reviewed on 27 Nov 2024

Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
See all 150 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.