A mountain range with a prominent peak, dense forest, and a clear sky.

Trail Holiday Rentals

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Our top choices for Trail holiday rentals

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, (18 reviews)
"Cozy spot, clean and quiet. Cute place!"
United States
Cassandra R.
The price is NZ$346
includes taxes & fees
17 Aug - 18 Aug
Luxury studio in the private hillside of Trail. Wi-Fi & Pet Friendly!

2. 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, (17 reviews)
"Comfortable beds, nice layout!"
United States
katie w.
The price is NZ$494
includes taxes & fees
23 Aug - 24 Aug
The Shady Knoll ~ Crater Lake Basecamp ~ Hot tub ~ King Suite

3. A beautiful Skyfall Landing

A beautiful Skyfall Landing
Eagle Point
10.0 out of 10, Exceptional, (12 reviews)
"We like it because it was nice and quite staying out of the city it was great "
United States
Jose P.
The price is NZ$791
includes taxes & fees
31 Aug - 1 Sept
A beautiful Skyfall Landing

4. Private Queen Room w/ Bathroom

Private Queen Room w/ Bathroom
White City
10.0 out of 10, Exceptional, (10 reviews)
"Very nice place to stay."
United States
Anonymous traveller
The price is NZ$189
includes taxes & fees
17 Aug - 18 Aug
Private Queen Room w/ Bathroom

5. 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, (126 reviews)
"We had such an amazing relaxing weekend at this little hidden jewel, tucked away in Central Point. "
United States
Chris A.
The price is NZ$274
includes taxes & fees
23 Aug - 24 Aug
Pet Friendly, Light-filled, Organic Studio, Full Kitchen, Hot Tub

6. This house is a 4 bedroom(s), 2 bathrooms, located in Eagle Point, OR.

This house is a 4 bedroom(s), 2 bathrooms, located in Eagle Point, OR.
Eagle Point
10.0 out of 10, Exceptional, (23 reviews)
"The home was a wonderful stay for us!"
United States
Charles S.
The price is NZ$829
includes taxes & fees
15 Sept - 16 Sept
This house is a 4 bedroom(s), 2 bathrooms, located in Eagle Point, OR.

7. 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, (53 reviews)
"Perfect place for a quiet getaway "
United States
Jan G.
The price is NZ$300
includes taxes & fees
10 Sept - 11 Sept
Serene Historic Cabin, Nine Acre Estate, Just Off I-5

8. 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$466
includes taxes & fees
23 Aug - 24 Aug
Starwood Sanctuary

9. Crater Lake Themed Retreat in Eagle Point

Crater Lake Themed Retreat in Eagle Point
Eagle Point
10.0 out of 10, Exceptional, (4 reviews)
"The property was clean, had everything we needed, and a friendly host."
United States
Kylie K.
The price is NZ$401
includes taxes & fees
1 Sept - 2 Sept
Crater Lake Themed Retreat in Eagle Point

10. 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, (4 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$591
includes taxes & fees
18 Aug - 19 Aug
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.

11. Chic & cozy 1 bedroom guest-house

Chic & cozy 1 bedroom guest-house
Medford
9.8 out of 10, Exceptional, (16 reviews)
"Clean, cozy, and private.This was a pleasant and comfy experience.The pillows are exquisite!I liked it."
United States
Sebastian T.
The price is NZ$306
includes taxes & fees
17 Aug - 18 Aug
Chic & cozy 1 bedroom guest-house

12. Union Creek Resort

Union Creek Resort
3.0 star property
Prospect
8.0 out of 10, Very good, (1,018 reviews)
"Quiet, relaxed atmosphere. Exactly what we needed to unplug and reset."
United States
SARAH
The price is NZ$265
includes taxes & fees
16 Sept - 17 Sept
Union Creek Resort

13. Creekside Retreat House in Eagle Point

Creekside Retreat House in Eagle Point
Eagle Point
9.6 out of 10, Exceptional, (4 reviews)
"I love the cleanliness of this place."
United States
Diem
The price is NZ$461
includes taxes & fees
17 Aug - 18 Aug
Creekside Retreat House in Eagle Point

14. Restful River Retreat

Restful River Retreat
Gold Hill
9.2 out of 10, Wonderful, (38 reviews)
"Great host, beautiful location. "
United States
Amy G.
The price is NZ$389
includes taxes & fees
19 Aug - 20 Aug
Restful River Retreat

15. Little Wolf Tiny Home cozy, pet friendly, secluded

Little Wolf Tiny Home cozy, pet friendly, secluded
Central Point
8.8 out of 10, Excellent, (6 reviews)
"everything was advertised, nice and quite, well maintained and kept. Would stay again."
Canada
william L.
The price is NZ$244
includes taxes & fees
17 Aug - 18 Aug
Little Wolf Tiny Home cozy, pet friendly, secluded

16. 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, (26 reviews)
"Couldn't be happier with my experience. Loved the location, privacy, cleanliness, and prompt replies of the host. Will be making this my preferred lodging while traveling for work in the area. "
United States
Jeff L.
The price is NZ$406
includes taxes & fees
17 Aug - 18 Aug
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!

17. Situated in a Gold Hill neighborhood that offers the convenience of I-5 access and the beauty of Rogue River views. A perfect, quick stopover point.

Situated in a Gold Hill neighborhood that offers the convenience of I-5 access and the beauty of Rogue River views. A perfect, quick stopover point.
Gold Hill
9.0 out of 10, Wonderful, (13 reviews)
"It was a great peaceful respite between the events around my father's "
United States
Wendi M.
The price is NZ$268
includes taxes & fees
17 Aug - 18 Aug
Situated in a Gold Hill neighborhood that offers the convenience of I-5 access and the beauty of Rogue River views. A perfect, quick stopover point.

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

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 reviews)
"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$249
includes taxes & fees
17 Aug - 18 Aug
Enjoy the tranquility of a scenic riverside neighborhood in Gold Hill. This area is peaceful, offers beautiful views, and is a convenient stopover location.

19. Relaxing Retreat in East Medford

Relaxing Retreat in East Medford
Medford
9.6 out of 10, Exceptional, (9 reviews)
"Host is fabulous and so is the home"
United States
Scott F.
The price is NZ$672
includes taxes & fees
26 Aug - 27 Aug
Relaxing Retreat in East Medford

20. 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
10.0 out of 10, Exceptional, (1 review)
The price is NZ$474
includes taxes & fees
30 Aug - 31 Aug
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!
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

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?

"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. Another good choice for your trip to Trail is 'RIVER HAVEN' is a serene riverside cabin on the Rogue River.

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?

Lost Creek Park and Rogue River are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Spirit of the Rogue Nature Center. Rogue River-Siskiyou National Forest and Umpqua National Forest 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.