Holiday Homes in Trail

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Check prices for these dates

Our top choices for Trail holiday homes

1. 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$588
includes taxes & fees
16 Nov - 17 Nov
Skyfall Landing

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, (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

3. 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

4. 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

5. 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.

6. 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

7. 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

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

Charming 2BR Cottage • Near Freeway-Cul-de-sac
Medford
9.2 out of 10, Wonderful, (16 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$315
includes taxes & fees
16 Nov - 17 Nov
Charming 2BR Cottage • Near Freeway-Cul-de-sac

9. 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

10. Restful River Retreat

Restful River Retreat
Gold Hill
9.4 out of 10, Exceptional, (44 reviews)
"Great host, beautiful location. "
United States
Amy G.
The price is NZ$432
includes taxes & fees
17 Nov - 18 Nov
Restful River Retreat

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

Family & Dog Friendly-LG Kitchen-Gazebo &Fire Pit-
Medford
10.0 out of 10, Exceptional, (3 reviews)
"Beds were super comfortable and house was perfect! "
United States
Jessica S.
The price is NZ$443
includes taxes & fees
16 Nov - 17 Nov
Family & Dog Friendly-LG Kitchen-Gazebo &Fire Pit-

12. Blissful Solitude Cottage

Blissful Solitude Cottage
Douglas County
10.0 out of 10, Exceptional, (8 reviews)
"It is a nice place to stay"
United States
Matthew O.
The price is NZ$307
includes taxes & fees
1 Dec - 2 Dec
Blissful Solitude Cottage

13. 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

14. Relaxing Retreat in East Medford

Relaxing Retreat in East Medford
Medford
9.6 out of 10, Exceptional, (10 reviews)
"This house is well equipped and very clean. The Host, Deanna, was very accommodating and communicated well. We enjoyed our 3 day stay very much. We would come back to this house again in the future while in Medford."
United States
Kathryn F.
Relaxing Retreat in East Medford

15. 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$377
includes taxes & fees
7 Dec - 8 Dec
Orchard House, Orchard House Retreat

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.

17. Beautiful & Comfortable Home in Central Point

Beautiful & Comfortable Home in Central Point
Central Point
9.8 out of 10, Exceptional, (7 reviews)
"The house was lovely and the host was quick to communicate."
United States
Vince K.
The price is NZ$609
includes taxes & fees
15 Nov - 16 Nov
Beautiful & Comfortable Home in Central Point

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

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

Quiet 3BR Home w/ Fenced Yard Near Airport
Medford
8.4 out of 10, Very good, (5 reviews)
"Easy check in.. would reccommend more lighting outside for safety and ability to see the front entrance. "
United States
Jinger S.
The price is NZ$565
includes taxes & fees
6 Dec - 7 Dec
Quiet 3BR Home w/ Fenced Yard Near Airport

20. 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$447
includes taxes & fees
16 Nov - 17 Nov
HOT TUB! Firepit - Bright Open-Near Airport & Freeway
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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