Trail Vacations from $335

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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.
Hummingbird Estate Wine & Suites

Hummingbird Estate Wine & Suites

4.5 out of 5
Price was $386, price is now $335 per person
$335
per person
Mar 13 - Mar 15
found 13 hours ago
Roundtrip flight included
Los Angeles (LAX) to Medford (MFR)
9.6/10 Exceptional! (145 reviews)
A beautiful place to relax and enjoy life. Excellent service at the wine bar. The room was comfortable, clean and overall exceeded expectations.

Reviewed on Jan 4, 2026

Compass by Margaritaville in Medford

Compass by Margaritaville in Medford

4 out of 5
Price was $708, price is now $571 per person
$571
per person
Apr 20 - Apr 24
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Medford (MFR)
9.6/10 Exceptional! (1,003 reviews)
The feel of being in a little tropical paradise right in Medford. The restaurant is a perfect little get away and the breakfast in the morning is fantastic. Great staff. Super clean.

Reviewed on Jan 28, 2026

A Cowslip's Belle Inn

A Cowslip's Belle Inn

3 out of 5
Price was $718, price is now $605 per person
$605
per person
Apr 20 - Apr 24
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Medford (MFR)
9.8/10 Exceptional! (40 reviews)
Lovely yard courtyard area with koi pond

Reviewed on Aug 25, 2025

McCall House Boutique Inn

McCall House Boutique Inn

4 out of 5
Historic Downtown District
Price was $1,007, price is now $852 per person
$852
per person
Apr 20 - Apr 24
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Medford (MFR)
9.2/10 Wonderful! (574 reviews)
Absolutely beautiful hotel. Our stay was wonderful!

Reviewed on Jan 31, 2026

Ashland Hills Hotel & Suites

Ashland Hills Hotel & Suites

3 out of 5
Price was $630, price is now $548 per person
$548
per person
Apr 20 - Apr 24
found 12 hours ago
Roundtrip non-stop flight included
Detroit (DTT) to Medford (MFR)
9/10 Wonderful! (1,497 reviews)
Great hotel I highly recommend 😊

Reviewed on Jan 26, 2026

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Discover the most popular places to visit in Trail

Lost Creek Park

Explore the great outdoors at Lost Creek Park, a lovely green space in Trail. Wander the riverfront in this relaxing 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 quaint 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! (165 reviews)
The location is just beautiful. But no one said anything about the traffic noise which can be very loud, especially at night. We did not sleep well. The other thing that kept us up was small black flies that were inside the lamps beside the bed. They come alive at night and hop all over you. We couldnt ...

Reviewed on Dec 20, 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
"Home on The Rogue" - Gateway to Crater Lake!

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

Trail OR
9.8/10 Exceptional! (99 reviews)
Very nicely furnished, clean and well organized home located on the Rogue. It had all the amenities you would want in a rental.The property was beautiful with the river flowing through the backyard. However, the house is facing a major road so it was very noisy, especially at night when trying to ...

Reviewed on Oct 8, 2025

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"Home on The Rogue" - Gateway to Crater Lake!
See all 162 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 $335 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.