Trail Vacations from $196

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Your Trail Vacation

There's no better way to travel than with one of our vacation packages to Trail. The outdoorsy activities and adventurous activities are two of the countless reasons you'll want to visit this interesting city. A trip to Trail wouldn't be complete without exploring a few popular attractions, like Spirit of the Rogue Nature Center. Whoever you're traveling with and whatever your bank balance, your dream Trail vacation is only clicks away with Expedia.

The Latest Trail vacation packages

Price found within the past 48 hours. Click for updated prices.
Clarion Pointe Medford

Clarion Pointe Medford

2.5 out of 5
Price was $277, price is now $196 per person
$196
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
8/10 Very Good! (1,077 reviews)
Food (if it can be called that) was horrible. I couldn't tell what the sausage was made of, the eggs were powdered? nasty! Service

Reviewed on Dec 17, 2025

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $397, price is now $294 per person
$294
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (1,003 reviews)
Love staying at this hotel! Clean, comfortable beds, good happy hour and great breakfast!

Reviewed on Dec 14, 2025

Rogue Regency Inn and Suites

Rogue Regency Inn and Suites

3 out of 5
Price was $326, price is now $253 per person
$253
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9/10 Wonderful! (2,611 reviews)
Great room. Very Clean

Reviewed on Dec 16, 2025

Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Save 100% on your flight
Price was $729, price is now $573 per person
$573
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (145 reviews)
We had an amazing stay at the Hummingbird Estate. The staff was so welcoming and our room was so cozy. Definitely will be back!

Reviewed on Dec 9, 2025

Ashland Springs Hotel

Ashland Springs Hotel

3 out of 5
Historic Downtown District
Price was $417, price is now $329 per person
$329
per person
Jan 28 - Jan 31
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.2/10 Wonderful! (1,000 reviews)
Beautiful hotel, lovely room, and the front desk person was really kind. Unfortunate that they charge a $15/day fee for Parking/Gym/Wifi amenities that they hide in small print.... that was not cool. We didn't use the gym nor parking. Other than that, beautiful hotel, great location.

Reviewed on Dec 17, 2025

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Discover the most popular places to visit in Trail

Lost Creek Park

4/5(2 reviews)

Explore the great outdoors at Lost Creek Park, a lovely green space in Trail. Wander the riverfront in this quaint area.

Lost Creek Park

Cole M. Rivers Hatchery

Explore the great outdoors at Cole M. Rivers Hatchery, a lovely green space in Trail. Wander the riverfront in this relaxing area.

Cole M. Rivers Hatchery

Spirit of the Rogue Nature Center

Enjoy an outing to Spirit of the Rogue Nature Center during your stay in Trail. Wander the riverfront in this quaint area.

Spirit of the Rogue Nature Center

Trail Hotel Deals

*Riverfront* "Cabin on The Rogue", Gateway to Crater Lake! Sleeps 2-4

*Riverfront* "Cabin on The Rogue", Gateway to Crater Lake! Sleeps 2-4

Trail OR
9.8/10 Exceptional! (164 reviews)
Owner was super responsive to small issue we had. Loved the river front back yard.

Reviewed on Oct 15, 2025

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*Riverfront* "Cabin on The Rogue", Gateway to Crater Lake! Sleeps 2-4
Romantic & private cabin on Rogue River, 1 hr from Crater Lake

Romantic & private cabin on Rogue River, 1 hr from Crater Lake

Trail OR
9.8/10 Exceptional! (405 reviews)
Amazing stay! Every detail of the cabin was thoughtful. The kitchen was fully stocked with all cooking utensils plus coffee and half n half. We stayed for thanksgiving and I was able to bake my pie in the oven which was really helpful. The spa and sauna were the icing on the cake. The host was very ...

Reviewed on Nov 29, 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 OR
$192 nightly
The price is $195 total per night from Dec 19 to Dec 20
$195 total
Dec 19 - Dec 20
Total with taxes and fees
9.2/10 Wonderful! (14 reviews)
Loved the solitude and my Yorkie pups loved the coy pond.The sleeping accommodations are the reason for 4 stars not very comfortable.Host was VERY RESPONSIVE to our questions and needs.

Reviewed on Nov 25, 2025

Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
See all 157 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.

Find the Best Trail Vacation Packages

Trail Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Rogue Valley Intl. Airport (MFR)
Population
700
Top Sights
Joseph H Stewart State Park, Joseph H. Stewart State Recreation Area and Cole M. Rivers Hatchery

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Frequently asked questions

How much does a Trail vacation package cost?
You'll find cheap prices from $196 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 vacation to Trail costs.
What are the cheapest months to go to Trail?
January, October and December are great times to search for cheap Trail vacation packages. Traveling in quieter periods means you can usually find reduced prices on hotels and flights.
How many days is enough for Trail?
Generally, a handful of days is enough to explore the main attractions during your Trail vacation. But if you want to have more time to rest or go on day tours, consider extending your itinerary.
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 vacation as a package?
You can enjoy significant savings on your Trail break by booking a tailored vacation 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 vacation 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.
Does Expedia offer Book Now, Pay Later Trail vacation packages?
Secure your perfect trip to Trail with help from our Book Now, Pay Later vacations. No need to scrimp and save or wait for payday — we've joined forces with online lender Affirm to offer you flexibility and choice. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no hidden charges or late payment fees, you can easily stick to your budget and snap up bargains while they last.

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.