A town nestled in a valley with a prominent building in the foreground and hills in the background.

Holiday Homes in Southern Oregon

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Southern Oregon holiday homes

1. Basecamp GP Private Unit in Quiet Duplex

Basecamp GP Private Unit in Quiet Duplex
3.5 star property
Grants Pass
10.0 out of 10, Exceptional, (4 reviews)
"Easy location to find, quiet neighborhood, comfy beds and perfect for my dogs. I would recommend people to stay there."
United States
Chantelle
The price is NZ$310
includes taxes & fees
6 Dec - 7 Dec
Basecamp GP Private Unit in Quiet Duplex

2. Whimsy on B

Whimsy on B
3.0 star property
Historic Railroad District
The price is NZ$298
includes taxes & fees
15 Nov - 16 Nov
Whimsy on B

3. Barclay Klum House by WanderLodges

Barclay Klum House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (10 reviews)
"Great ~ memorable stay. "
United States
Melissa
The price is NZ$459
includes taxes & fees
6 Dec - 7 Dec
Barclay Klum House by WanderLodges

4. Savage Upon Siskiyou

Savage Upon Siskiyou
3.0 star property
Siskiyou-Hargadine Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Had an amazing stay, thank you!"
United States
megan
The price is NZ$629
includes taxes & fees
15 Nov - 16 Nov
Savage Upon Siskiyou

5. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (11 reviews)
"Stunning views!! A+++ Experience!!"
United States
Jose
The price is NZ$652
includes taxes & fees
2 Dec - 3 Dec
Grandview of Ashland

6. Whimsy On B 2br & Studio

Whimsy On B 2br & Studio
2.5 star property
Historic Railroad District
The price is NZ$574
includes taxes & fees
16 Nov - 17 Nov
Whimsy On B 2br & Studio

7. Redwoods Stopover by WanderLodges

Redwoods Stopover by WanderLodges
2.0 star property
Cave Junction
10.0 out of 10, Exceptional, (4 reviews)
"Beautiful home. My truck didn’t fit in the garage but there’s a gate that I was able to park it behind. Support staff were super helpful."
United States
Braden
The price is NZ$373
includes taxes & fees
19 Nov - 20 Nov
Redwoods Stopover by WanderLodges

8. Hanna's House by WanderLodges

Hanna's House by WanderLodges
4.0 star property
Historic Railroad District
10.0 out of 10, Exceptional, (6 reviews)
"Very cute cottage, 10 min walk to OSF theaters. It has everything you need - full kitchen, front room, and AC for the hot summers! Owner very kind. Will stay there again!"
United States
Robert
The price is NZ$322
includes taxes & fees
19 Nov - 20 Nov
Hanna's House by WanderLodges

9. Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is NZ$240
includes taxes & fees
15 Nov - 16 Nov
Rosewood Studio by WanderLodges

10. Riverside Cabin 5 - (Brand New Construction)

Riverside Cabin 5 - (Brand New Construction)
Grants Pass
10.0 out of 10, Exceptional, (109 reviews)
"We had a great stay and look forward to returning"
United States
Nancy
The price is NZ$231
includes taxes & fees
4 Dec - 5 Dec
Riverside Cabin 5 - (Brand New Construction)

11. The Mountain Ave House by WanderLodges

The Mountain Ave House by WanderLodges
4.0 star property
Ashland
10.0 out of 10, Exceptional, (8 reviews)
"Lovely space and very comfortable; walkable from downtown "
United States
Joyce
The price is NZ$536
includes taxes & fees
15 Nov - 16 Nov
The Mountain Ave House by WanderLodges

12. 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$433
includes taxes & fees
6 Dec - 7 Dec
Starwood Sanctuary

13. Cottage 9 – Downtown Jacksonville Retreat Steps from Shops & Britt Gardens

Cottage 9 – Downtown Jacksonville Retreat Steps from Shops & Britt Gardens
Jacksonville Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Great place to stay while visiting the Rogue Valley. In the heart of Jacksonville, a walking distance to all of the quaint shops, restaurants and Britt Festival!"
United States
Denise M.
The price is NZ$369
includes taxes & fees
13 Nov - 14 Nov
Cottage 9 – Downtown Jacksonville Retreat Steps from Shops & Britt Gardens

14. Spacious Western Home on 2 acres in the Pines close to Crater Lake

Spacious Western Home on 2 acres in the Pines close to Crater Lake
Chiloquin
10.0 out of 10, Exceptional, (152 reviews)
"Lovely and LOTS of space for a family of 4!"
United States
Krista L.
The price is NZ$535
includes taxes & fees
15 Nov - 16 Nov
Spacious Western Home on 2 acres in the Pines close to Crater Lake

15. The Rellik House and Winery

The Rellik House and Winery
3.5 star property
Central Point
9.4 out of 10, Exceptional, (6 reviews)
"A perfect place to enjoy the winery and countryside! Staff were responsive and friendly!"
United States
Kimberlee
The price is NZ$625
includes taxes & fees
9 Dec - 10 Dec
The Rellik House and Winery

16. Cedar Mountain - Suite E

Cedar Mountain - Suite E
Grants Pass
10.0 out of 10, Exceptional, (87 reviews)
"We loved our stay in Grants Pass. Will definitely be back."
United States
Angela H.
The price is NZ$253
includes taxes & fees
23 Nov - 24 Nov
Cedar Mountain - Suite E

17. Tilty House in the Hidden Hills

Tilty House in the Hidden Hills
Downtown Klamath Falls
9.4 out of 10, Exceptional, (22 reviews)
"Very well updated, kitchen is definitely tilty but we enjoyed our stay and it was close to the graduation festivities."
United States
Juanitta P.
The price is NZ$336
includes taxes & fees
13 Nov - 14 Nov
Tilty House in the Hidden Hills

18. Bear Mountain -Suite 6

Bear Mountain -Suite 6
Grants Pass
10.0 out of 10, Exceptional, (10 reviews)
"We enjoyed our stay. Plenty of room for our family of 5. Was clean and well taken care of with large TV, full kitchen, fridge and laundry. The kids loved the cute log cabin style. It was the perfect stop over on our way to an Alaskan cruise."
United States
Katherine E.
The price is NZ$275
includes taxes & fees
11 Dec - 12 Dec
Bear Mountain -Suite 6

19. East Main Downtown Bungalow

East Main Downtown Bungalow
Historic Railroad District
9.2 out of 10, Wonderful, (56 reviews)
"Fantastic spot, walkable to anything in downtown. Well-appointed, clean, easy. Definitely recommend."
United States
Melissa D.
The price is NZ$370
includes taxes & fees
17 Nov - 18 Nov
East Main Downtown Bungalow

20. Hanna`s House | Downtown Retreat, Steps to OSF

Hanna`s House | Downtown Retreat, Steps to OSF
Historic Railroad District
10.0 out of 10, Exceptional, (171 reviews)
"Excellent quaint cottage….great location….easy check in….very well stocked and very comfortable….second year at this cottage and will be back next year!!"
United States
Jim L.
The price is NZ$393
includes taxes & fees
15 Nov - 16 Nov
Hanna`s House | Downtown Retreat, Steps to OSF
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Southern Oregon Hotel Reviews

Find out more about Southern Oregon

Southern Oregon Holiday Homes information

Number of reviews
658
Accommodation
509 Holiday Homes
Lowest Price
NZ$231
Highest Price
NZ$652

Explore a world of travel with Expedia