Trail Holiday Rentals

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Our top choices for Trail holiday rentals

Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!

Trail
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 AU$299
includes taxes & fees
13 Dec - 14 Dec
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!

On-site Winery & Tasting Room: Oregon Bungalow!

3.0 star property
Central Point
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 AU$332
includes taxes & fees
14 Dec - 15 Dec
On-site Winery & Tasting Room: Oregon Bungalow!

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Central Point
9.8 out of 10, Exceptional, (101)
"This was just what we needed as our halfway point of our trip. Area was quiet and close torestaurants. L9ved our stay here. It was a very hot day, but we were able to remain cool here."
United States
carol A.
The price is AU$270
includes taxes & fees
14 Dec - 15 Dec
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

Private Queen Room w/ Bathroom

White City
10.0 out of 10, Exceptional, (8)
"Very nice place to stay."
United States
Anonymous traveller
The price is AU$171
includes taxes & fees
23 Dec - 24 Dec
Private Queen Room w/ Bathroom

Serene Historic Cabin, Nine Acre Estate, Just Off I-5

Gold Hill
9.6 out of 10, Exceptional, (42)
"Such great communication, and overall a great stay!"
United States
Kathryn W.
The price is AU$251
includes taxes & fees
19 Dec - 20 Dec
Serene Historic Cabin, Nine Acre Estate, Just Off I-5

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

Gold Hill
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 AU$338
includes taxes & fees
11 Dec - 12 Dec
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

Comfy Cozy Casa

Medford
10.0 out of 10, Exceptional, (56)
"Great place to stay "
United States
Artem V.
The price is AU$451
includes taxes & fees
6 Jan - 7 Jan 2026
Comfy Cozy Casa

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!

Gold Hill
10.0 out of 10, Exceptional, (22)
"The hot tub was awesome, gorgeous of the river. Situated nicely between Medford and Grants pass with a short drive to either. Hosts were communicative and pleasant. All necessities that could be reasonably expected on site. Shower has great water pressure. "
United States
Alexis B.
The price is AU$322
includes taxes & fees
14 Dec - 15 Dec
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!

Blissful Solitude Cottage

Douglas County
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 AU$270
includes taxes & fees
16 Dec - 17 Dec
Blissful Solitude Cottage

Enjoy the tranquility of a scenic riverside neighborhood in Gold Hill. This area is peaceful, offers beautiful views, and is a convenient stopover location.

Gold Hill
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 AU$218
includes taxes & fees
11 Dec - 12 Dec
Enjoy the tranquility of a scenic riverside neighborhood in Gold Hill. This area is peaceful, offers beautiful views, and is a convenient stopover location.

Located in a scenic area perfect for travelers along I-5. You are right by the Rogue River, offering stunning views and tranquility, yet conveniently positioned for easy travel access.

Gold Hill
9.0 out of 10, Wonderful, (4)
"Loved the river view. Very clean and good sized. Great host. Would definitely stay again."
United States
Daniel B.
The price is AU$236
includes taxes & fees
23 Dec - 24 Dec
Located in a scenic area perfect for travelers along I-5. You are right by the Rogue River, offering stunning views and tranquility, yet conveniently positioned for easy travel access.

Little Wolf Tiny Home cozy, pet friendly, secluded

Central Point
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 AU$219
includes taxes & fees
23 Dec - 24 Dec
Little Wolf Tiny Home cozy, pet friendly, secluded

Restful River Retreat

Gold Hill
9.0 out of 10, Wonderful, (28)
"Beautiful place!"
United States
Lonna P.
The price is AU$311
includes taxes & fees
7 Jan - 8 Jan 2026
Restful River Retreat

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

Medford
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 AU$358
includes taxes & fees
19 Dec - 20 Dec
Charming 2BR Cottage • Near Freeway-Cul-de-sac

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

Medford
9.8 out of 10, Exceptional, (9)
"Stayed in this place for one night while passing through and it was a great stay! It was clean, spacious and the beds were comfortable!"
United States
Marissa M.
The price is AU$623
includes taxes & fees
21 Dec - 22 Dec
HOT TUB! Firepit - Bright Open-Near Airport & Freeway

A beautiful Skyfall Landing

Eagle Point
10.0 out of 10, Exceptional, (9)
"The property was great! The pool was amazing and Jennifer was a wonderful host. I will definitely come back. "
United States
Jared F.
The price is AU$511
includes taxes & fees
14 Dec - 15 Dec
A beautiful Skyfall Landing

Cozy Tiny House! Small But Mighty ~ Comfy & Gorgeous Location

Central Point
10.0 out of 10, Exceptional, (10)
"I had a lovely stay at the Bee home! I loved the location and how peaceful it was! The place had everything one would need in a clean and compact package. I was able to see the meteor shower on my second night there. I would definitely stay there again!"
United States
Shannon S.
The price is AU$244
includes taxes & fees
22 Dec - 23 Dec
Cozy Tiny House! Small But Mighty ~ Comfy & Gorgeous Location

King Bed Guest Studio w/covered parking, private patio, Kitchenette,

Medford
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 AU$211
includes taxes & fees
14 Dec - 15 Dec
King Bed Guest Studio w/covered parking, private patio, Kitchenette,

The Shady Knoll - Peace & Quiet near the Rogue River!

Shady Cove
10.0 out of 10, Exceptional, (7)
"Really nice and quiet. Plus shady cove is a nice town. Great spot for fishing, hiking and some golf. As advertised. "
United States
Timothy G.
The price is AU$374
includes taxes & fees
11 Dec - 12 Dec
The Shady Knoll - Peace & Quiet near the Rogue River!

Starry Skies Campout

Douglas County
The price is AU$130
includes taxes & fees
18 Dec - 19 Dec
Starry Skies Campout
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.
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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 favourite 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 depend 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 AU$251 per night. Entering your travel dates in the search wizard might find you 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.