Book Holiday Homes in Trail

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Featured Holiday Homes in Trail

Whether you're here to explore the Rogue River, Crater Lake, or the Britt Festival, this location is the perfect home base for your Southern Oregon experience!

Whether you're here to explore the Rogue River, Crater Lake, or the Britt Festival, this location is the perfect home base for your Southern Oregon experience!

Central Point OR
The price is AU$420 per night from 31 Jan to 1 Feb
AU$420
31 Jan - 1 Feb
includes taxes & fees
With a stay at this vacation home in Central Point, you'll be within a 10-minute walk of Rogue Creamery and Central Point Library.
Opens in a new windowWhether you're here to explore the Rogue River, Crater Lake, or the Britt Festival, this location is the perfect home base for your Southern Oregon experience!
Family Friendly Great Location Inviting and Comfortable Lovely Clean Home

Family Friendly Great Location Inviting and Comfortable Lovely Clean Home

Central Point OR
Located in Central Point, this vacation home is within a 5-minute drive of Crater Rock Museum and Rogue Creamery.
Opens in a new windowFamily Friendly Great Location Inviting and Comfortable Lovely Clean Home
Comfy Cozy Casa

Comfy Cozy Casa

Medford OR
The price is AU$351 per night from 1 Feb to 2 Feb
AU$351
1 Feb - 2 Feb
includes taxes & fees
A stay at this vacation home places you in the heart of Medford, a 4-minute drive from Providence Medford Medical Center and 5 minutes from Cinemark Tinseltown ...
Opens in a new windowComfy Cozy Casa
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Restful River Retreat

Restful River Retreat

Gold Hill OR
The price is AU$326 per night from 2 Feb to 3 Feb
AU$326
2 Feb - 3 Feb
includes taxes & fees
Located in Gold Hill, this vacation home is on a river, within a 5-minute walk of Rogue River and Gold Hill Library.
Opens in a new windowRestful River Retreat
East Medford Home Getaway

East Medford Home Getaway

2 out of 5
Medford OR
The price is AU$386 per night from 1 Feb to 2 Feb
AU$386
1 Feb - 2 Feb
includes taxes & fees
Located in Medford, this vacation home is a 5-minute drive from Medford Railroad Park and 5 minutes from Providence Medford Medical Center.
Opens in a new windowEast Medford Home Getaway
The Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7

The Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7

Eagle Point OR
The price is AU$424 per night from 31 Jan to 1 Feb
AU$424
31 Jan - 1 Feb
includes taxes & fees
When you stay at this vacation home in Eagle Point, you'll be in the mountains, within a 5-minute drive of Eagle Point Library and Butte Creek Mill.
Opens in a new windowThe Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7
HOT TUB! Firepit - Bright Open-Near Airport & Freeway

HOT TUB! Firepit - Bright Open-Near Airport & Freeway

Medford OR
The price is AU$385 per night from 4 Feb to 5 Feb
AU$385
4 Feb - 5 Feb
includes taxes & fees
With a stay at this vacation home in Medford, you'll be within a 5-minute drive of Providence Medford Medical Center and Cinemark Tinseltown Medford 15.
Opens in a new windowHOT TUB! Firepit - Bright Open-Near Airport & Freeway
Charming 2BR Cottage • Near Freeway-Cul-de-sac

Charming 2BR Cottage • Near Freeway-Cul-de-sac

Medford OR
The price is AU$294 per night from 3 Feb to 4 Feb
AU$294
3 Feb - 4 Feb
includes taxes & fees
With a stay at this vacation home in Medford, you'll be within a 5-minute drive of Providence Medford Medical Center and Medford Railroad Park.
Opens in a new windowCharming 2BR Cottage • Near Freeway-Cul-de-sac
This is a 3 bedroom 2 bath home with large backyard. In the back of the property features a 1 bedroom fully equipped guest house with a gate from the backyard for easy access.

This is a 3 bedroom 2 bath home with large backyard. In the back of the property features a 1 bedroom fully equipped guest house with a gate from the backyard for easy access.

Central Point OR
The price is AU$771 per night from 1 Feb to 2 Feb
AU$771
1 Feb - 2 Feb
includes taxes & fees
With a stay at this vacation home in Central Point, you'll be within a 10-minute walk of Rogue Creamery and Central Point Library.
Opens in a new windowThis is a 3 bedroom 2 bath home with large backyard. In the back of the property features a 1 bedroom fully equipped guest house with a gate from the backyard for easy access.
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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.

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
64 Holiday Homes
Lowest Price
AU$294
Highest Price
AU$771
Popular accommodation
Whether you're here to explore the Rogue River, Crater Lake, or the Britt Festival, this location is the perfect home base for your Southern Oregon experience!, Family Friendly Great Location Inviting and Comfortable Lovely Clean Home, Comfy Cozy Casa, Restful River Retreat, East Medford Home Getaway, The Fairway Townhouse | Minutes from Golf Course | Sleeps Up To 7, HOT TUB! Firepit - Bright Open-Near Airport & Freeway, Charming 2BR Cottage • Near Freeway-Cul-de-sac, This is a 3 bedroom 2 bath home with large backyard. In the back of the property features a 1 bedroom fully equipped guest house with a gate from the backyard for easy access.

Top trending hotels in Trail

*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
With a stay at this cabin in Trail, you'll be on the waterfront, just steps from Rogue River and a 3-minute drive from Shady Cove Library.
Opens in a new window*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
With a stay at this cabin in Trail, you'll be on a river, just steps from Rogue River and a 3-minute drive from Shady Cove Library.
Opens in a new windowRomantic & 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
Located in Trail, this vacation home is on the waterfront, a 5-minute drive from Rogue River and 9 minutes from Spirit of the Rogue Nature Center.
Opens in a new window"Home on The Rogue" - Gateway to Crater Lake!
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Riverfront Stunning Open Concept 3bdrm near outdoor activities

Riverfront Stunning Open Concept 3bdrm near outdoor activities

Trail OR
With a stay at this vacation home in Trail, you'll be steps from Rogue River and a 4-minute drive from Shady Cove Library.
Opens in a new windowRiverfront Stunning Open Concept 3bdrm near outdoor activities
Don't see what you're looking for?
See all available properties in Trail
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.