Book Holiday Homes in Trail
More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)
We keep it easy with the option to pay now or later on select accommodation
Book up 'til the last second - millions of rooms to crash tonight^
Featured Holiday Homes in Trail

Comfy Cozy Casa

Spectacular large custom home with a pool!

Cozy creekside home with deck, 15 min to airport, shopping, 1 hr to Crater Lk.

Fully equipped house on the river with a private fishing hole.

Eagle Point Golf Retreat w/ Patio + Grill!

Charming Rogue Valley Home in Central Point!

Cheerful 3-Bedroom home in Central Point

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

Shady Cove River House -Fly Fish, Raft, Hike or Just Relax
Trail Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Trail vacation homes are the perfect way for you to wing it.
Holiday houses in Trail let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Trail in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Trail adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Trail with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Trail vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Trail Holiday Homes essential information
Accommodation | 66 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Comfy Cozy Casa, Spectacular large custom home with a pool!, Cozy creekside home with deck, 15 min to airport, shopping, 1 hr to Crater Lk. , Fully equipped house on the river with a private fishing hole., Eagle Point Golf Retreat w/ Patio + Grill!, Charming Rogue Valley Home in Central Point!, Cheerful 3-Bedroom home in Central Point, "Home on The Rogue" - Gateway to Crater Lake!, Shady Cove River House -Fly Fish, Raft, Hike or Just Relax |
More accommodations in Trail
Top trending hotels in Trail

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

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

Fully equipped house on the river with a private fishing hole.

Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
More ways to explore Trail
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.