Trail Holiday Rentals

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Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Trail holiday rentals

A wooden table with two chairs, each with a floral cushion, positioned by a window overlooking a forested area.

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

Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
Trail
9.0 out of 10, Wonderful, (20 reviews)
"Cozy spot, clean and quiet. Cute place!"
United States
Cassandra R.
The price is NZ$333
includes taxes & fees
16 Nov - 17 Nov
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!
A swimming pool with a clear view of a forested hillside in the background.

2. River Retreat with Pool, Pond, and Trails/Gateway to Crater Lake

River Retreat with Pool, Pond, and Trails/Gateway to Crater Lake
Trail
10.0 out of 10, Exceptional, (1 review)
"Beautiful property right on the river. The owner and family live on the property but lots of space that we barely saw another person. A definite plus that we could bring our dogs. Trails all around the property. The house was absolutely beautiful. Recently remodeled. Lots of wildlife on the property. Accessible river fishing on site. It was a nice quiet reset. Lots of great stargazing too."
United States
Kerrie P.
The price is NZ$511
includes taxes & fees
15 Nov - 16 Nov
River Retreat with Pool, Pond, and Trails/Gateway to Crater Lake
A patio with a glass table and chairs, overlooking a grassy area with trees and a body of water.

3. Private Rogue River Cabin For Two/Gateway to Crater Lake

Private Rogue River Cabin For Two/Gateway to Crater Lake
Trail
10.0 out of 10, Exceptional, (2 reviews)
"Perfect location for trip to Crater Lake National Park! Great communication also!!"
United States
Wendy G.
The price is NZ$436
includes taxes & fees
15 Nov - 16 Nov
Private Rogue River Cabin For Two/Gateway to Crater Lake
A view through a window with a stone-paved area and a grassy lawn leading to a wooded area with trees and a body of water.

4. Riverside 2 Bedroom Cabin on Rogue River/Gateway to Crater Lake

Riverside 2 Bedroom Cabin on Rogue River/Gateway to Crater Lake
Trail
The price is NZ$562
includes taxes & fees
16 Nov - 17 Nov
Riverside 2 Bedroom Cabin on Rogue River/Gateway to Crater Lake
A covered outdoor seating area with a dark-colored sofa and a glass-top coffee table, surrounded by a wooden deck and a grassy lawn.

5. The Shady Knoll ~ Crater Lake Basecamp ~ Hot tub ~ King Suite

The Shady Knoll ~ Crater Lake Basecamp ~ Hot tub ~ King Suite
Shady Cove
10.0 out of 10, Exceptional, (21 reviews)
"Great place to stay. Highly recommend!!"
United States
Troy P.
The price is NZ$488
includes taxes & fees
1 Dec - 2 Dec
The Shady Knoll ~ Crater Lake Basecamp ~ Hot tub ~ King Suite
A swimming pool with two people floating on inner tubes.

6. Skyfall Landing

Skyfall Landing
Eagle Point
10.0 out of 10, Exceptional, (14 reviews)
"Beautiful and comfortable space"
United States
sarah k.
The price is NZ$601
includes taxes & fees
15 Nov - 16 Nov
Skyfall Landing
A campfire, wooden chairs, and a bench in a forested area with a view of a bridge.

7. Union Creek Resort

Union Creek Resort
3.0 star property
Prospect
8.0 out of 10, Very good, (1,121 reviews)
"Nice area with lots of hiking access, nice for a weekend getaway"
United States
Brett
The price is NZ$156
includes taxes & fees
18 Nov - 19 Nov
Union Creek Resort
A covered outdoor seating area with wooden tables and chairs, a barbecue grill, and a building in the background.

8. Relax, Reconnect, Explore Scenic Retreat + Pool, Treehouses & Adventure Nearby

Relax, Reconnect, Explore Scenic Retreat + Pool, Treehouses & Adventure Nearby
White City
10.0 out of 10, Exceptional, (4 reviews)
"Great vrbo for the price and for a cozy, laid back stay."
United States
Heather W.
The price is NZ$967
includes taxes & fees
20 Nov - 21 Nov
Relax, Reconnect, Explore Scenic Retreat + Pool, Treehouses & Adventure Nearby
An outdoor seating area with a fire pit, two Adirondack chairs, and a view of a lake surrounded by trees.

9. Creekside Retreat House - Christmas Decoration

Creekside Retreat House - Christmas Decoration
Eagle Point
9.8 out of 10, Exceptional, (6 reviews)
"Great location close to town was very clean peaceful setting with the creek"
United States
jeffery c.
The price is NZ$359
includes taxes & fees
20 Nov - 21 Nov
Creekside Retreat House - Christmas Decoration
A modern living room with a sofa, a television, a fireplace, and a decorative wall.

10. Crater Lake Themed Retreat in Eagle Point

Crater Lake Themed Retreat in Eagle Point
Eagle Point
10.0 out of 10, Exceptional, (8 reviews)
"What a beautiful place. Had a great time staying here"
Canada
Hengda
The price is NZ$371
includes taxes & fees
15 Nov - 16 Nov
Crater Lake Themed Retreat in Eagle Point
A cozy living room with a stone fireplace, a leather sofa, and a view of the outdoors through large windows.

11. Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails

Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails
Prospect
10.0 out of 10, Exceptional, (247 reviews)
"We appreciated that the lodging was remote enough to be quiet, and offered hiking opportunities within steps of the home. The kitchen was particularly well equipped, making it easy for meal preparation."
United States
Anonymous traveller
The price is NZ$664
includes taxes & fees
15 Nov - 16 Nov
Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails
A covered porch with wooden railings, wicker furniture, and a white door.

12. Escape to Alta Vista Retreat, a peaceful mountain getaway offering stunning views and a relaxing hot tub. Enjoy a private, comfortable stay surrounded by nature, with plenty of space to unwind and reconnect.

Escape to Alta Vista Retreat, a peaceful mountain getaway offering stunning views and a relaxing hot tub. Enjoy a private, comfortable stay surrounded by nature, with plenty of space to unwind and reconnect.
Eagle Point
9.6 out of 10, Exceptional, (5 reviews)
"Loved the home! Amazing views, so relaxing with all the accommodations! This will be my go to place when I am in town."
United States
liz
The price is NZ$616
includes taxes & fees
15 Nov - 16 Nov
Escape to Alta Vista Retreat, a peaceful mountain getaway offering stunning views and a relaxing hot tub. Enjoy a private, comfortable stay surrounded by nature, with plenty of space to unwind and reconnect.
A modern living room with a grey sofa, wooden flooring, a flat-screen TV, a desk with a chair, and a patterned rug.

13. Starwood Sanctuary

Starwood Sanctuary
3.0 star property
Medford
9.4 out of 10, Exceptional, (3 reviews)
"I was able to have early check in. The private bathroom off the main room was tiny. Coffee and cocoa were nice. The beds were comfy but the accent lights didn’t work and the shampoo dispenser was broken. Price and location were nice.. may book again.. spider webs outside 🤔😊"
United States
Erin
The price is NZ$435
includes taxes & fees
6 Dec - 7 Dec
Starwood Sanctuary
A white house with a porch, two Adirondack chairs, a tree with hanging flowers, and a birdhouse.

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

Serene Historic Cabin, Nine Acre Estate, Just Off I-5
Gold Hill
9.6 out of 10, Exceptional, (58 reviews)
"The property is beautiful, it’s quiet and excluded from reality. Definitely somewhere to come to get away from city life or just needing a break. Also, if you’re a dog person they have the best welcome pup Finnley who loves coming to say hi!"
United States
Garry A.
The price is NZ$274
includes taxes & fees
15 Nov - 16 Nov
Serene Historic Cabin, Nine Acre Estate, Just Off I-5
Private kitchen

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

Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
Central Point
9.8 out of 10, Exceptional, (130 reviews)
"Wonderful stay and will definitely do so again!!!"
United States
Kelly B.
The price is NZ$304
includes taxes & fees
16 Nov - 17 Nov
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub
A covered porch with wooden railings, wicker furniture, and a white door.

16. Remodeled 3 BR/2.5 BA Retreat near Eagle Point. Includes main house and a private cottage. Group-friendly kitchen, famous waffle bar, hot tub, and electric fireplace. Great space for cooking and connecting.

Remodeled 3 BR/2.5 BA Retreat near Eagle Point. Includes main house and a private cottage. Group-friendly kitchen, famous waffle bar, hot tub, and electric fireplace. Great space for cooking and connecting.
Eagle Point
10.0 out of 10, Exceptional, (1 review)
"Great house and a beautiful location. Host was incredibly easy to work with."
United States
Timothy C.
The price is NZ$782
includes taxes & fees
15 Nov - 16 Nov
Remodeled 3 BR/2.5 BA Retreat near Eagle Point. Includes main house and a private cottage. Group-friendly kitchen, famous waffle bar, hot tub, and electric fireplace. Great space for cooking and connecting.
A modern kitchen with white cabinets, a central island, and bar stools.

17. Comfy Cozy Casa

Comfy Cozy Casa
Medford
9.8 out of 10, Exceptional, (82 reviews)
"The property was definitely as advertised and we would stay there again."
United States
DANA W.
The price is NZ$503
includes taxes & fees
16 Nov - 17 Nov
Comfy Cozy Casa
A bedroom with a bed, bedside table, lamp, window, and a view of the outdoors.

18. Mount McLoughlin Mountain View Ranch; Near Crater Lake; sleeps up to 12

Mount McLoughlin Mountain View Ranch; Near Crater Lake; sleeps up to 12
Prospect
10.0 out of 10, Exceptional, (2 reviews)
"This home and location was perfect for our family. Would visit again without hesitation."
United States
Curtis G.
The price is NZ$888
includes taxes & fees
17 Nov - 18 Nov
Mount McLoughlin Mountain View Ranch; Near Crater Lake; sleeps up to 12
A covered outdoor seating area with wicker furniture and a view of a forested area.

19. The Sleepy Canoe - A Cozy River front house near everything in Southern Oregon

The Sleepy Canoe - A Cozy River front house near everything in Southern Oregon
Gold Hill
9.6 out of 10, Exceptional, (111 reviews)
"A beautiful home and great service!"
United States
Laurie s.
The price is NZ$708
includes taxes & fees
15 Nov - 16 Nov
The Sleepy Canoe - A Cozy River front house near everything in Southern Oregon
A hot tub with a wooden bench and a table, surrounded by a railing, overlooking a river and hilly landscape.

20. 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!

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
9.8 out of 10, Exceptional, (28 reviews)
"Great accommodations, excellent communication. We all had a great time!"
United States
Sabrina D.
The price is NZ$428
includes taxes & fees
16 Nov - 17 Nov
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!
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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Find holiday rentals that suit your style

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Top Trail Hotel Reviews

A wooden deck with outdoor seating overlooking a river, surrounded by trees and a natural landscape.
Riverfront Lodging

Riverfront Lodging

Riverfront Lodging
Shady Cove

10/10 Excellent

Great two bedroom unit, very helpfull staff, the rear deck was wonderful looking over the river waving at the paddlers enjoying a beer. Much appreciated. . Bob
Australia
Bob
Reviewed September 8, 2024
Riverfront Lodging

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$155 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. Make the most of games in this rental home to help you unwind.

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.