Photo by Kaitlin Walters

Trail Holiday Rentals

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Holiday Rentals in Trail

Romantic & private cabin on Rogue River, 1 hr from Crater Lake
10.0 out of 10, Exceptional, (455)
"This is a historical cabin on the Rogue River. Like most historical cabins it is small and dark. Fortunately the outdoor space is amazing. This is the perfect place to go for any season except for winter when it would be too dark. It does need some updating. The kitchen is outfitted to match the time of the cabin. Sorting out the fridge and the oven/stove was a little challenging. There is not much room for groceries and it is definitely a one person kitchen. There is a bar to sit at but would...
Romantic & private cabin on Rogue River, 1 hr from Crater Lake
'RIVER HAVEN' is a serene riverside cabin on the Rogue River
10.0 out of 10, Exceptional, (17)
"The home was very clean and charming. We cooked full meals each night and found the kitchen well stocked with fresh, new cookware, dishes and utensils. The pictures and description of the backyard were very accurate. It was gorgeous, peaceful and so relaxing. Very convenient 5 minutes drive to the store and restaurants. We will be going back. Thanks Vicky."
'RIVER HAVEN' is a serene riverside cabin on the Rogue River
Fully equipped house on the river with a private fishing hole.
10.0 out of 10, Exceptional, (21)
"Perfect place to stay for a relaxing adventure. It's about 1 hour away from the Crater Lake Lodge and an easy drive. The house is clean and comfortable. The outdoor area by the river is covered so you can enjoy even when it's raining. Our only critique was that there was only one kitchen towel for use. I would suggest a few more for guests that like to cook and do not want to waste paper towels."
Fully equipped house on the river with a private fishing hole.
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Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
The price is NZ$273
includes taxes & fees
30 May - 31 May
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
Riverfront Stunning Open Concept 3bdrm near outdoor activities
8.0 out of 10, Very good, (5)
"This cabin by the river had great views and was clean. Even though the water in the river was high, both levels of the backyard were dry enough for use in May. It was relaxing to sit on the back porch and drink coffee in the morning or cider in the afternoon. Bring your sleeping mask since sunrise is early, but beautiful. Every room has wonderful views of outside. Plenty of room for a family of 4-5 without sleeping on a couch. We would stay here again."
Riverfront Stunning Open Concept 3bdrm near outdoor activities
Cozy retreat on 3 acres near Lost Creek Lake. Pet Friendly
Cozy retreat on 3 acres near Lost Creek Lake. Pet Friendly
Adorable 1 bedroom cottage on the river.
Adorable 1 bedroom cottage on the river.
Red Blanket Cabin Near Crater Lake National Park
10.0 out of 10, Exceptional, (337)
"This place has it all!"
Red Blanket Cabin Near Crater Lake National Park
Shady Cove River House -Fly Fish, Raft, Hike or Just Relax
9.8 out of 10, Exceptional, (135)
"Love the property cute and cozy. Kitchen was awesome. They didn’t miss any details. Outside was amazing to have river and peaceful surrounding while being in a quiet neighborhood. Close to town, store and restaurants. Will be back in springtime. "
Shady Cove River House -Fly Fish, Raft, Hike or Just Relax
Renovated Home in Central Point
10.0 out of 10, Exceptional, (13)
"Very clean and comfortable house in a nice quiet neighborhood. Everything about our booking and check in process was seamless."
Renovated Home in Central Point
Chic Medford Retreat - Outdoor Pool & Sauna!
10.0 out of 10, Exceptional, (4)
"Absolutely perfect place to stay for a family. Everything was clean and we’ll done. So many fun thinks for kids to do. And parents will love the master bedroom."
Chic Medford Retreat - Outdoor Pool & Sauna!
Restful River Retreat
9.8 out of 10, Exceptional, (10)
"Great find on our way home. The second bunk is higher than a normal bunk and none of our kids would sleep up there because it didn't feel protected enough to them. Would be great for ages 10+. The cookware is great, but it was sparse on basics. We would stopover again if it works with our itinerary."
The price is NZ$339
includes taxes & fees
31 May - 1 Jun
Restful River Retreat
Comfy Cozy Casa
10.0 out of 10, Exceptional, (25)
"The home was beautiful and well stocked. Beds were comfy. I will recommend this home to friends."
The price is NZ$482
includes taxes & fees
3 Jun - 4 Jun
Comfy Cozy Casa
Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails
10.0 out of 10, Exceptional, (191)
"This is a whole house with a big backyard for wildlife viewing. It is conveniently located to local sites; a 3-ring binder is provided in the house with information. This house was spotlessly clean, comfortable and quiet. The hosts were very warm and helpful. This is a 5 star location."
The price is NZ$678
includes taxes & fees
30 May - 31 May
Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails
Cozy getaway located near the Rogue River and the beautiful Crater Lake
Cozy getaway located near the Rogue River and the beautiful Crater Lake
Cheerful 3-Bedroom home in Central Point
10.0 out of 10, Exceptional, (16)
"Worked great as a home base for visiting family for the holidays. Easy access to anywhere in the rogue valley and folks could easily come to us too so we didn’t have to load the kids up to visit or eat"
The price is NZ$608
includes taxes & fees
2 Jun - 3 Jun
Cheerful 3-Bedroom home in Central Point
Serene Historic Cabin, Nine Acre Estate, Just Off I-5
10.0 out of 10, Exceptional, (14)
"A lovely semi-rural setting with helpful/responsive hosts. The cabin is basic but comfortable with excellent beds. Hunting-themed art and trophies on the walls. Lots of natural light during the day, but would have liked reading lamps for nighttime use. Loved the trees, grasses, and birds."
The price is NZ$282
includes taxes & fees
6 Jun - 7 Jun
Serene Historic Cabin, Nine Acre Estate, Just Off I-5
Blue Gate Cottage on the Rogue River
9.8 out of 10, Exceptional, (17)
"So grateful for the quality of this place that takes pets! When someone is staying in the Lodge next door it’s good to at least meet each other, and cooperate to share the outdoor spaces. Plenty of room for everyone. Lovely part of the Rogue Valley."
Blue Gate Cottage on the Rogue River
Spectacular large home with seasonal pool.
9.8 out of 10, Exceptional, (7)
"We had good room for our group. Everything was clean and everything worked well. We entertained family there one night. Thank you so much for helping our family get together and just enjoy ourselves worry-free."
Spectacular large home with seasonal pool.
This fishing themed cottage is a perfect road trip stop along I-5
8.8 out of 10, Excellent, (6)
"This was a great place to stay near town and river. Good size and clean. Would stay again"
The price is NZ$249
includes taxes & fees
30 May - 31 May
This fishing themed cottage is a perfect road trip stop along I-5
Don't see what you're looking for?
See all available 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.

Other types of properties in Trail you may be interested in

Fully equipped house on the river with a private fishing hole.
10.0 out of 10, Exceptional, (21)
"Perfect place to stay for a relaxing adventure. It's about 1 hour away from the Crater Lake Lodge and an easy drive. The house is clean and comfortable. The outdoor area by the river is covered so you can enjoy even when it's raining. Our only critique was that there was only one kitchen towel for use. I would suggest a few more for guests that like to cook and do not want to waste paper towels."
Fully equipped house on the river with a private fishing hole.
Romantic & private cabin on Rogue River, 1 hr from Crater Lake
10.0 out of 10, Exceptional, (455)
"This is a historical cabin on the Rogue River. Like most historical cabins it is small and dark. Fortunately the outdoor space is amazing. This is the perfect place to go for any season except for winter when it would be too dark. It does need some updating. The kitchen is outfitted to match the time of the cabin. Sorting out the fridge and the oven/stove was a little challenging. There is not much room for groceries and it is definitely a one person kitchen. There is a bar to sit at but would...
Romantic & private cabin on Rogue River, 1 hr from Crater Lake
'RIVER HAVEN' is a serene riverside cabin on the Rogue River
10.0 out of 10, Exceptional, (17)
"The home was very clean and charming. We cooked full meals each night and found the kitchen well stocked with fresh, new cookware, dishes and utensils. The pictures and description of the backyard were very accurate. It was gorgeous, peaceful and so relaxing. Very convenient 5 minutes drive to the store and restaurants. We will be going back. Thanks Vicky."
'RIVER HAVEN' is a serene riverside cabin on the Rogue River
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Trail holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Trail. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Trail. Seeing all the best attractions is bound to make you fall in love with Trail. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Trail short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Trail?

Yes, there are holiday rentals in Trail close to Spirit of the Rogue Nature Center, or you can select a more secluded option if you're looking for a relaxing stay. Trail is known for its riverfront.

What are some of the best holiday rentals that Trail has to offer?

Fully equipped house on the river with a private fishing hole.: This highly rated holiday home rental in Trail is located on a river, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind. Some other top choices in Trail are 'RIVER HAVEN' is a serene riverside cabin on the Rogue River and Riverfront Stunning Open Concept 3bdrm near outdoor activities .

How many holiday rentals are there in Trail?

Expedia has 6 holiday rentals for your stay in Trail.

What can I see and do in Trail?

Rogue River and Rogue River-Siskiyou National Forest are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Spirit of the Rogue Nature Center. Umpqua National Forest and Lost Creek Park are other places to visit while you're in town.

What are holiday rentals like in Trail?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Trail. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can offer a sense of seclusion away from public hotel lifts and bustling concierge desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.

Recent reviews of Trail properties
Expedia verified reviews