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

Search Vacation 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
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Southern Oregon vacation homes

A modern living room with a wooden dining table, a bench, and a fireplace.

1. 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 P8,715
P16,392 total
includes taxes & fees
Sep 29 - Sep 30
Redwoods Stopover by WanderLodges
A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

2. 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 P8,715
P17,728 total
includes taxes & fees
Sep 29 - Sep 30
Barclay Klum House by WanderLodges
A covered patio with a hammock chair, outdoor furniture, and a garden area with a stone pathway.

3. 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, (1 review)
The price is P7,028
P12,870 total
includes taxes & fees
Sep 29 - Sep 30
Basecamp GP Private Unit in Quiet Duplex
A modern living room with a grey sofa, wooden flooring, a flat-screen TV, a desk with a chair, and a patterned rug.

4. 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 P8,715
P18,169 total
includes taxes & fees
Sep 29 - Sep 30
Starwood Sanctuary
A deck with a fire pit, outdoor seating, and a view of the countryside.

5. Grandview of Ashland

Grandview of Ashland
3.0 star property
Ashland
10.0 out of 10, Exceptional, (9 reviews)
"The Grandview house and property far exceeded our expectations. We especially enjoying making meals together in the beautiful kitchen and reminiscing on the deck while taking in the spectacular views. We were fortunate to see lots of wildlife too. We hope to come back next year."
United States
Sonja
The price is P16,812
P29,683 total
includes taxes & fees
Oct 4 - Oct 5
Grandview of Ashland
A kitchen with a stainless steel sink, wooden cabinets, a black stove, and a window with curtains.

6. Rosewood Studio by WanderLodges

Rosewood Studio by WanderLodges
3.0 star property
Medford
The price is P7,366
P11,449 total
includes taxes & fees
Sep 29 - Sep 30
Rosewood Studio by WanderLodges
A modern living room with a wooden floor, a sofa, a coffee table, and a kitchen area in the background.

7. 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 P14,557
P25,555 total
includes taxes & fees
Sep 29 - Sep 30
The Rellik House and Winery
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Southern Oregon Hotel Reviews

Stratford Inn

Stratford Inn

8/10 Good
"Clean and plain but very nice, convient and a real Shakespeare vibe."
Richard 5-night trip
Posted 2 hours ago
Stratford Inn

Find out more about Southern Oregon

Southern Oregon Vacation Homes information

Number of reviews
32
Accommodation
39 Vacation Homes
Lowest Price
P11,449
Highest Price
P29,683

Explore a world of travel with Expedia