Photo by Kaitlin Walters

Trail Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Trail holiday rentals

9.2 out of 10, Wonderful, (15)
"We enjoyed a quiet evening. Everything was kept tidy and was a good place for us to stop for the evening."
United States
Mary P.
The price is NZ$332
includes taxes & fees
1 Jan - 2 Jan 2026
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
3.0 star property
8.4 out of 10, Very good, (5)
"Loved our stay at the Bungalow. The owners were so welcoming, helpful and friendly. The bungalow was very clean and had well equipped. It wa a great location for everything we wanted to do. The bungalow was even nicer than the pictures. We would definitely recommend this stay! "
United States
Deborah
The price is NZ$327
includes taxes & fees
31 Jan - 1 Feb 2026
On-site Winery & Tasting Room: Oregon Bungalow!
9.8 out of 10, Exceptional, (102)
"Super cute place! Perfectly located in the middle of things. Food and drink near by."
United States
Rachel B.
The price is NZ$266
includes taxes & fees
2 Jan - 3 Jan 2026
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
10.0 out of 10, Exceptional, (22)
"We had an incredible stay at this serene riverside retreat along the Rogue River. The home was spotless, well-equipped, and thoughtfully maintained—everything we needed for a comfortable getaway. Although a nearby wildfire caused a brief power outage, it didn’t dampen our experience. The host was communicative and gracious throughout, and the location is perfect for exploring Crater Lake National Park and the surrounding natural beauty. We’d gladly return for another visit!"
United States
Vishnu
The price is NZ$355
includes taxes & fees
3 Jan - 4 Jan 2026
Charming 2 BR riverside stopover in Gold Hill. Private hot tub, river access, and just down the road from Del Rio Vineyards. Perfect base for exploring the Rogue Valley. Pet-friendly!
3.0 star property
10.0 out of 10, Exceptional, (1)
"The rooms were spotless, spacious and welcomed. Thank you "
United States
Eva
The price is NZ$541
includes taxes & fees
11 Jan - 12 Jan 2026
Clearview Comfort 3BR Near Airport

Holiday Home in White City

Private Queen Room w/ Bathroom
10.0 out of 10, Exceptional, (8)
"Very nice place to stay."
United States
Anonymous traveller
The price is NZ$192
includes taxes & fees
6 Jan - 7 Jan 2026
Private Queen Room w/ Bathroom
9.6 out of 10, Exceptional, (42)
"Very clean & comfortable beds!"
United States
Luke E.
The price is NZ$268
includes taxes & fees
7 Jan - 8 Jan 2026
Serene Historic Cabin, Nine Acre Estate, Just Off I-5
9.2 out of 10, Wonderful, (17)
"The place was super cute and updated. The hot tub had been cleaned and refilled with fresh water, which was very nice. I feel we had some trouble with the keypad which should be looked into. Other than that it was a great quiet weekend. Will rent again for sure."
United States
Michele R.
The price is NZ$378
includes taxes & fees
4 Jan - 5 Jan 2026
R&R on the Rogue River! This 2 BR cottage in Gold Hill features a private hot tub with stunning scenic views. Enjoy a spacious, private setting perfect for relaxation, adventure, or remote work

Holiday Home in Douglas County

Blissful Solitude Cottage
10.0 out of 10, Exceptional, (4)
"My trip actually got canceled last minute, but the communication with the host was absolutely amazing and I will absolutely rebook as soon as possible"
United States
steve
The price is NZ$306
includes taxes & fees
22 Jan - 23 Jan 2026
Blissful Solitude Cottage

Holiday Home in Gold Hill

Restful River Retreat
9.2 out of 10, Wonderful, (29)
"Beautiful place!"
United States
Lonna P.
The price is NZ$358
includes taxes & fees
14 Jan - 15 Jan 2026
Restful River Retreat
9.4 out of 10, Exceptional, (14)
"This was our second time staying at this property and once again we had a great experience. The house is so cozy and comfortable. The neighborhood is very quite. And the location is great. We will definitely be back!"
United States
EmilieC
The price is NZ$362
includes taxes & fees
13 Jan - 14 Jan 2026
Charming 2BR Cottage • Near Freeway-Cul-de-sac
9.2 out of 10, Wonderful, (7)
"The location worked well for us, and the view of the river at the back of the property was beautiful!"
United States
Nick D.
The price is NZ$265
includes taxes & fees
7 Jan - 8 Jan 2026
Ideal stopover location right off I-5, nestled in a scenic area by the Rogue River. Enjoy the peaceful sounds of the river while having quick access to major travel routes and nearby towns.

Holiday Home in Medford

Comfy Cozy Casa
10.0 out of 10, Exceptional, (57)
"Great place to stay "
United States
Artem V.
The price is NZ$515
includes taxes & fees
20 Jan - 21 Jan 2026
Comfy Cozy Casa
9.8 out of 10, Exceptional, (12)
"Our stay was ok. The place was clean and roomy. Trying to wash dishes in the bathroom sink was awkward. "
United States
Karyn S.
The price is NZ$238
includes taxes & fees
1 Jan - 2 Jan 2026
King Bed Guest Studio w/covered parking, private patio, Kitchenette,
10.0 out of 10, Exceptional, (4)
"everything was advertised, nice and quite, well maintained and kept. Would stay again."
Canada
william L.
The price is NZ$248
includes taxes & fees
1 Jan - 2 Jan 2026
Little Wolf Tiny Home cozy, pet friendly, secluded

Holiday Home in Douglas County

Orchard House, Orchard House Retreat
10.0 out of 10, Exceptional, (1)
"Fantastic place to spend the holiday very serene very peaceful"
United States
Gin H.
The price is NZ$336
includes taxes & fees
14 Jan - 15 Jan 2026
Orchard House, Orchard House Retreat
9.0 out of 10, Wonderful, (2)
"The room was so clean.it had everything you needed in the kitchen.was very comfy bed.easy walk down to the river.Great view.I would recommend it to everyone.Thanks for the pet treats.Also was a very guiet place to stay."
United States
Mark B.
The price is NZ$247
includes taxes & fees
8 Jan - 9 Jan 2026
Enjoy the tranquility of a scenic riverside neighborhood in Gold Hill. This area is peaceful, offers beautiful views, and is a convenient stopover location.
10.0 out of 10, Exceptional, (8)
"We had everything we would possibly need.The house was very nicely laid out and we spent a lot of time on the back deck. Saw turkeys and a family of deer in the yard. Would definitely stay again. "
United States
Cheri I.
The price is NZ$387
includes taxes & fees
1 Jan - 2 Jan 2026
The Shady Knoll - Peace & Quiet near the Rogue River!

Holiday Home in Medford

Large kitchen! Quiet Cul-de-sac!
9.2 out of 10, Wonderful, (36)
"We loved the place, the amount of space, the fenced yard with doggy door and all the extra little amenities. It was a stopover on a long trip for us and it was so nice to just relax and have our own space away from each other."
United States
Hannah M.
The price is NZ$439
includes taxes & fees
20 Jan - 21 Jan 2026
Large kitchen! Quiet Cul-de-sac!
9.8 out of 10, Exceptional, (16)
"Comfy & Cozy. Great communication from owner. A wonderful place and exactly as described. "
United States
Aviary P.
The price is NZ$312
includes taxes & fees
1 Jan - 2 Jan 2026
Chic & cozy 1 bedroom guest-house
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Trail Hotel Reviews

Find out more about Trail

Everything you need to know about Trail holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Trail holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Trail holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Trail holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Trail. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Trail holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Trail holiday rentals we have selected for you start as low as NZ$266 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Trail rentals

At Expedia, we put the best Trail holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Trail rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Trail holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Trail. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

"Home on The Rogue" - Gateway to Crater Lake!: This highly rated holiday home rental in Trail is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Trail?

Expedia has 7 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.