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

Holiday Homes in Trail

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Trail holiday homes

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.

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

The Shady Knoll ~ Crater Lake Basecamp ~ Hot tub ~ King Suite
Shady Cove
9.8 out of 10, Exceptional, (18 reviews)
"Comfortable beds, nice layout!"
United States
katie w.
The price is NZ$517
includes taxes & fees
5 Oct - 6 Oct
The Shady Knoll ~ Crater Lake Basecamp ~ Hot tub ~ King Suite
A swimming pool with two people floating on inner tubes.

2. Skyfall Landing

Skyfall Landing
Eagle Point
10.0 out of 10, Exceptional, (14 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$629
includes taxes & fees
12 Oct - 13 Oct
Skyfall Landing
A modern kitchen with a large island, stainless steel appliances, and wooden cabinets.

3. 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, (25 reviews)
"The home was a wonderful stay for us!"
United States
Charles S.
The price is NZ$822
includes taxes & fees
1 Oct - 2 Oct
This house is a 4 bedroom(s), 2 bathrooms, located in Eagle Point, OR.
An outdoor seating area with a fire pit, two Adirondack chairs, and a view of a lake surrounded by trees.

4. Creekside Retreat House in Eagle Point

Creekside Retreat House in Eagle Point
Eagle Point
9.8 out of 10, Exceptional, (6 reviews)
"I love the cleanliness of this place."
United States
Diem
The price is NZ$376
includes taxes & fees
7 Oct - 8 Oct
Creekside Retreat House in Eagle Point
A modern living room with a sofa, a television, a fireplace, and a decorative wall.

5. Crater Lake Themed Retreat in Eagle Point

Crater Lake Themed Retreat in Eagle Point
Eagle Point
10.0 out of 10, Exceptional, (6 reviews)
"What a beautiful place. Had a great time staying here"
Canada
Hengda
The price is NZ$384
includes taxes & fees
1 Oct - 2 Oct
Crater Lake Themed Retreat in Eagle Point
A river surrounded by lush greenery and trees.

6. Restful River Retreat

Restful River Retreat
Gold Hill
9.4 out of 10, Exceptional, (43 reviews)
"Great host, beautiful location. "
United States
Amy G.
The price is NZ$406
includes taxes & fees
4 Oct - 5 Oct
Restful River Retreat
A covered porch with wooden railings, wicker furniture, and a white door.

7. 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$626
includes taxes & fees
1 Oct - 2 Oct
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 living room with a wooden dining table, a sofa, and a TV mounted on the wall.

8. Comfy Cozy Casa

Comfy Cozy Casa
Medford
9.8 out of 10, Exceptional, (78 reviews)
"This is a great place to stay!! We will stay here then next time we are in Medford visiting family. The house was so clean. The amenities were great too! Real comfortable and welcoming place to stay! I highly recommend."
United States
David S.
The price is NZ$544
includes taxes & fees
5 Oct - 6 Oct
Comfy Cozy Casa
A modern living room with a grey sofa, wooden flooring, a flat-screen TV, a desk with a chair, and a patterned rug.

9. 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$476
includes taxes & fees
11 Oct - 12 Oct
Starwood Sanctuary
A modern kitchen with wooden cabinets, stainless steel appliances, granite countertops, and a wood floor.

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

Charming 2BR Cottage • Near Freeway-Cul-de-sac
Medford
9.2 out of 10, Wonderful, (15 reviews)
"This little house is prefect for a homey, comfort place. The location is great. We will definitely be back"
United States
EmilieC
The price is NZ$388
includes taxes & fees
4 Oct - 5 Oct
Charming 2BR Cottage • Near Freeway-Cul-de-sac
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, (241 reviews)
"Had a wonderful time. Went by way too fast. Definitely will be going back will a longer stay! Thank you again for having us."
United States
Corey T.
The price is NZ$717
includes taxes & fees
18 Oct - 19 Oct
Meadow House near Crater Lake South entrance, upper Rogue River, 100 acre trails
A hot tub under a wooden pergola with a view of trees and hills.

12. Charming 2-bedroom riverfront cottage! Enjoy a wood stove, W/D, and private hot tub overlooking the Rogue River. Perfect Gold Hill getaway for couples or a small family retreat.

Charming 2-bedroom riverfront cottage! Enjoy a wood stove, W/D, and private hot tub overlooking the Rogue River. Perfect Gold Hill getaway for couples or a small family retreat.
Gold Hill
9.4 out of 10, Exceptional, (8 reviews)
"Great place to stay! The back deck overlooking the river was great for morning coffee and evening chats and the jacuzzi was a wonderdul treat :)"
United States
Lauren
The price is NZ$476
includes taxes & fees
14 Oct - 15 Oct
Charming 2-bedroom riverfront cottage! Enjoy a wood stove, W/D, and private hot tub overlooking the Rogue River. Perfect Gold Hill getaway for couples or a small family retreat.
A red deck with two Adirondack chairs and a stone fire pit in a forest setting.

13. Orchard House, Orchard House Retreat

Orchard House, Orchard House Retreat
Douglas County
10.0 out of 10, Exceptional, (3 reviews)
"Great little well needed romantic getaway!"
United States
Shawn M.
The price is NZ$334
includes taxes & fees
1 Oct - 2 Oct
Orchard House, Orchard House Retreat
A patio area with a blue sofa set, a small table with a vase of flowers, and a striped rug.

14. Beautiful & Comfortable Home in Central Point

Beautiful & Comfortable Home in Central Point
Central Point
9.6 out of 10, Exceptional, (4 reviews)
"The house was lovely and the host was quick to communicate."
United States
Vince K.
The price is NZ$614
includes taxes & fees
2 Oct - 3 Oct
Beautiful & Comfortable Home in Central Point
A covered outdoor seating area with wooden tables and chairs, a barbecue grill, and a building in the background.

15. 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$1,097
includes taxes & fees
31 Oct - 1 Nov
Relax, Reconnect, Explore Scenic Retreat + Pool, Treehouses & Adventure Nearby
A hotel room with a bed, a bedside table, a lamp, and a curtain.

16. 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$499
includes taxes & fees
1 Oct - 2 Oct
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!
Enjoy connecting around the porch firepit!

17. Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (8 reviews)
"Clean, beautiful property "
United States
Loyd H.
The price is NZ$350
includes taxes & fees
1 Oct - 2 Oct
Blissful Solitude Cottage
A kitchen with wooden cabinets, a white microwave, a stove, and a sink.

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

HOT TUB! Firepit - Bright Open-Near Airport & Freeway
Medford
9.8 out of 10, Exceptional, (9 reviews)
"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 NZ$558
includes taxes & fees
4 Oct - 5 Oct
HOT TUB! Firepit - Bright Open-Near Airport & Freeway
A modern living room with a sofa, a coffee table, a TV, and a bed with a blanket.

19. Family & Dog Friendly-LG Kitchen-Gazebo &Fire Pit-

Family & Dog Friendly-LG Kitchen-Gazebo &Fire Pit-
Medford
10.0 out of 10, Exceptional, (2 reviews)
"Beds were super comfortable and house was perfect! "
United States
Jessica S.
The price is NZ$696
includes taxes & fees
5 Oct - 6 Oct
Family & Dog Friendly-LG Kitchen-Gazebo &Fire Pit-
A modern living room with a grey wall, a wooden TV stand, a sofa, a coffee table with a plant, and a decorative lamp.

20. Quiet 3BR Home w/ Fenced Yard Near Airport

Quiet 3BR Home w/ Fenced Yard Near Airport
Medford
8.6 out of 10, Excellent, (4 reviews)
"Easy check in.. would reccommend more lighting outside for safety and ability to see the front entrance. "
United States
Jinger S.
Quiet 3BR Home w/ Fenced Yard Near Airport
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

Executive Residency by Best Western Medford

Executive Residency by Best Western Medford

10/10 Excellent
"Best Western took over this hotel recently. They've been upgrading each room. Thats why inside elevator and corridors are dirty but our room was brand new with small kitchen. No pots & pan nor dishes are available. No breakfast even though Hotels.com mentioned they did."
Yuko 3-night trip
Posted 11 hours ago
Executive Residency by Best Western Medford

Find out more about Trail

Trail Holiday Homes information

Number of reviews
428
Accommodation
69 Holiday Homes
Lowest Price
NZ$334
Highest Price
NZ$1,097